The HoneyDew with Ryan Sickler - Tim Dillon
Episode Date: January 27, 2020My HoneyDew this week is Tim Dillon! Tim returns to talk more about his parents - his mom is a former mermaid who currently suffers from schizophrenia and his dad is a former musician who is currently... still a former musician. Tim shares stories about hanging out in crack houses, doing cocaine and drinking in middle school. He also talks about coming out of the closet and what it was like when his subprime mortgage gig bottomed out. It’s a wild one! Sponsor: Go to http://omaxhealth.com today and enter code HONEYDEW to get 20% off CryoFreeze and sitewide!
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This episode of The Honeydew is brought to you by Omax Health.
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I want to tell you about some dates I have coming up here.
February 22nd, I'm at the Ice House in Pasadena, out in Pasadena, California, February 22nd.
March 19th through the 21st, I'm back in Phoenix at the House of Comedy.
Come on out, Phoenix.
And April 23rd through the 25th, I'll be up in Vancouver.
That's my first time up there.
Looking forward to that.
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Welcome back to The Honeydew, y'all.
We're over here at Studio Jeans doing it at your mom's house. I'm Ryan Sickler. Welcome back to the honeydew, y'all.
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And I fucking love you for it.
I love this show.
I love that it's resonating with you.
And I love that the people come on here and sit down and open up.
We're all going through some shit.
Everybody's going through some shit.
So if you can get away from it a little bit and laugh at it, it's a great thing.
We highlight the lowlights over here.
And as you know, these are the stories behind the storytellers.
And today's storyteller is a return guest first time on video ladies and
gentlemen tim dylan's on oh thank you so much thank you for coming back look who's at your
mom's house guys yeah i did it i made it i made it to the mecca officially and it's it's uh you
know how can you enjoy me without video you know that's translucent irish skin blister up in real time in front of you
how could you possibly but you need you hear my voice and then you hear the tragedy of what i'll
say and then i think the physical just brings it all together it's where people go around oh yeah
because that's what the show is right you want? You want to hear sad things from sad people that make it funny.
I mean, that's what the show is.
It's an exercise in masochism.
It is.
And you bring people on, and they talk about their horrible lives.
And some of the people you have on are successful,
and some of the people you have on are like me that are just clawing.
We're still clawing.
Clawing.
And it's nice to watch people look at a lot of your guests and go,
will they be people that I know in five years,
or will they be dead in the street?
And that's what I like about, that's what this show really is.
People are going, hey, I wonder if that guy will be a household name,
or will they find him dead in a hotel room in Tampa?
We don't know.
Who knows?
Who knows? Who knows?
It's definitely Florida.
It's just what the show is.
That's what the show is.
The best version of the show
is let's bring these people on.
We don't know if they're going to be successful.
Statistically, it's a real uphill battle.
And, you know...
I'd give you longer than five.
Yeah, well, I appreciate that.
For fame and death.
Oh, well, thank you.
I appreciate that. I know you got five in, well, thank you. I appreciate that.
I know you got five in your brother.
If anybody wants to come see me, Tim Dillon Comedy.
Yeah, please, promote everything.
TimDillonComedy.com.
You know, February, we're Zany's in Chicago,
5th through the 8th of February.
The Grand Gerard Theater in Ontario, Canada,
the 14th and the 15th.
New York Carolines, March 12th through 14th.
That'll be a big show.
It's my homecoming.
I'm from New York.
I live here now.
That's great.
And it's really going to be fun.
Bloomington,
Minneapolis,
House of Comedy,
April,
Phoenix,
Arizona,
House of Comedy,
May,
Comic Ship in Edmonton,
something in Vancouver,
whatever.
TimDillonComedy.com,
TimJDillon,
D-I-L-L-O-N on Instagram and Twitter.
And I put all that stuff there too.
Well, thank you for coming back.
Oh, well, thank you for having me.
Yeah, you were one of my early audio guests only.
I didn't want to stop podcasting.
I jumped right in after the crap he said
that the next week kicking off this honeydew year.
It was a therapeutic time when I did the show.
And it was the first time I had really met you
and talked to you or anything.
You were so open and honest. If you haven't't heard tim's first episode you have to go back
and listen um because we'll be jumping off from there but you talked about your mom was a mermaid
in florida at what's it called again the wiki watchy mermaid so many people have sent me this
yeah no a lot of people it connects with a lot of people you know and there's a lot of people out there
that have had it pretty rough yeah and they know all about the wiki watching mermaids in florida
which my mother my mother by the way very proud of that job it's not something that she has hidden
and it's not something she has called it her favorite job really many times what else has
your mom done so wait
let's in front of when we would go out when i'd have a friend as a kid we'd go out to dinner and
my mother would go i'm was a mermaid in florida and it was my favorite job and uh of course people
would be that would be the last play date i would have with that kid they'd be like oh okay
they go and tell their parents these people. These people are insane. Yeah.
Your dad was a musician.
He was a musician.
And met your mom there.
He met my mother.
Loved Blossoms and Boom. He was a Long Island, really good musician,
but didn't take it to the next level
because he never left Long Island
because the pull of a bacon, egg, and cheese sandwich
is too much.
He didn't go further.
But, like, I knew he was good because he doesn't really talk about that he was good.
But I will meet other people from Long Island that were like, oh, your dad was a good guy.
Really?
Yeah, he had a great band, and everybody loved him.
He was super talented.
And, you know, but it was like, you know, I just think he never pushed it.
And then he had me, and then he got, you know, he got a sales job and whatever.
But I came from that like. And is he, I can't remember, is he passed me and then he got you know he got a sales job and whatever and but i came from that like and is he i can't remember is he passed no he's still alive he's still alive and listens to most things i do um but he he had a studio in our house when we grew
up where he would make music uh and try to like you know he'd have a bunch of mixers and everything
and he would do jam with his friends and everything.
So he was and then he would still play out in bars when I was growing up.
Like he would play in bars on the weekends, you know, at the Coyote Grill in, you know, in Long Island, New York, you know.
So it never launched.
Quite obviously, it never went anywhere.
But he's still very good at it.
And at a family party he'll take
out his guitar and start playing so do you see him off wait so let's go back and just recap
you your parents split um your mom is i believe like my cousin a paranoid schizophrenic paranoid
schizophrenic although she's in a an institution it's uh we kind of had enough with her you know
um well that's the thing with
schizophrenics it's fun for a while yes but like anything else it starts to wear on you so we
locked her up um and she's good i visit her i visit her a lot tell me yeah and uh the last time
i visited her she said i just i she sat me down she goes i hope you're grateful about all the
great things donald trump is doing for this country oh my god and i said And I said, okay. And she goes, old Donald Trump, she goes,
I don't know why everyone's mad at him.
He just doesn't want Muslims to kill us.
And she goes, I don't know why Aunt Donna's mad at him for that.
Aunt Donna.
I don't know why Aunt Donna.
Maybe Aunt Donna wants Muslims to come kill us.
She goes, I don't want Muslims to come kill us.
I was like, well, this is.
And then she asked if I could get her a Make America Great Again hat.
And I said, no promises, but I might.
So she's doing good.
She's, hey, she's not all wrong, but she's not all right.
There's certain lines that stand out from your first episode where you said she mentioned something to you about your weight.
And you were like, hey, how about you worry about you?
You're in a mental institution. She's in a mental institution.
She's also obese.
But when I saw her, here's the thing about my mother.
She does understand things.
Like the last time she saw me, she goes, I said, hello.
This is true.
I said, hello.
Merry Christmas.
And she said, oh, Merry Christmas.
And then the first words out of her mouth, she goes,
you are too fat to be on TV
consistently
she goes they will put you on
every now and then but
you are too fat and she goes if you lose weight
maybe someone will give you money to fix your
teeth
and I said I don't even know
I don't even know if that
would work I don't even know who would do that
and then I was thinking maybe she's right if i lost 50 pounds would my agent fix my
teeth i mean they're not bad but i could cap them but so she's kind of like brutal but not
always wrong yeah no i know i i talked to my cousin and i can see these they're like these
pockets of clarity yeah i'm like oh whoa we're
having a real one here yeah he's with it he's he's clear he's conscious he's and it's not that
that you know that lost eyed glossy right look away in the deep space you know yeah yeah um
you also talked about and i will never forget this it I don't know why I curse you a little bit for it because I think about it on random days.
Yeah.
You talked about how you were a teenager and you used to go to this crack house and you would do drugs.
But hold on.
And there was a filthy cigarette burn stained blanket and a couch.
And you would pull that blanket up.
Yeah.
And you would take naps on that couch and
i was like oh that is so disgusting and you said what did i say you said you loved it i said i
loved it i don't i don't really trust anyone who hasn't done that i gotta be honest yeah i don't
trust anyone who hasn't pulled a cigarette stain blanket over themselves a burned blanket you have
in a crack house you have to try to experience the range of human experiences.
I don't know what to tell you.
Like, you know, sometimes people are in pain all over the place, right?
We know that.
But there's also a lot of, listen, there was a lot of fun in that crack house. I hear.
There were a lot of positive people.
I mean, I know I mean genuinely positive. I know you mean this, though.
Genuinely grateful and positive people.
Like, there were people there that if you gave them a cigarette
would act like you paid for their college.
So to me, it's like, how bad can it be?
Like, they were so.
I just remember how happy if you gave someone a cigarette, they would be happy.
And it's like, I know people with oodles of money and fame that just can't figure out how to be happy.
You're right about that.
And there's something just so beautiful and simple.
It's a binary.
Being a drug addict is a binary existence.
You're either high on drugs or you're looking for drugs.
There's a clarity to that.
It's not you don't want to live like that.
I'm not saying do it right but it gives
you a focus that many of my friends lack i i once heard that that you know there's a it was on the
internet somewhere but it said that that crackhead is going to get up today and he's going to go
hustle for that fucking crack and he's going to get that crack absolutely are you going to let a
crackhead out hustle you a hundred percent what are you watching gary v now is that a gary v it sounds like it are you gonna let that crackhead
out hustle you do you know what that crackhead does he grinds he hustles grinds his fucking teeth
there's a business inside of every crackhead um i watched him today though and he said the very
thing you did he mentioned friends he has that have make fifty thousand dollars a year and they're
happier than some of the people he knows that have a hundred million in the bank from the silicon
boom i know you know it doesn't buy happiness it doesn't buy happiness it helps it helps it
motherfucking helps but living in that environment right not living in it but being in it you know
and and and and seeing it kind of gave me an understanding of like you know what generational poverty was because a lot of
those people had children that's about that okay so let's let's talk about that because you're how
old you're a teenager i'm 17 right now you've got your whole life in front of you no i mean i'm 17
currently right i'm very big on tiktok i i'm what they call young sexy sexy Hollywood. I walk down the street and Hollywood producers.
My mother said the other day, by the way, she goes, there's a lot of Hollywood producers that try to have sex with children.
Has anyone tried to have sex with you?
I said, I look like I'm 64.
I don't know what.
How old would a producer have to be?
Stan Lee?
How old would someone have to be to?
But yeah, a lot of these people are kids.
At this point, I'm 14.
I'm 14.
You're 14.
You're a child.
I'm in eighth grade.
You're a child in a crack house.
13 or 14, yeah.
Surrounded by mostly adults.
They're adults.
And then my other buddy.
Who have kids. Shay went with me adults. They're adults. And then my other buddy. Who have kids.
Shay went with me and hung out with me.
But you also said you heard an adult one time say, if one of them ODs, we have to roll them up in the rug and put them out back.
Yeah, but of course.
It's like, what are we?
Yeah, I mean.
Yeah.
We laughed at that.
Did we laugh?
You know, because it's, of course, like, it's funny.
One of them said to the wife, I don't want to mention their names because I think they're still on Facebook.
By the way, everyone is on Facebook.
I thought they were all dead, and then I went on Facebook, and they were all on Facebook.
But, you know, it's funny.
I did another podcast where I talked about being a subprime mortgage guy and how everybody I was with was a thief
and would kill their mother and lie and cheat and steal and steal and then they all messaged me on instagram and
said brother i heard that podcast i love what you're doing you pegged us it was brilliant it
was beautiful they're like i hadn't remembered those days in so long i felt things i was crying
i was laughing i was like oh god it's a man but it's a man because you can't you know yeah um
but the thing about uh being young in that environment was we knew we shouldn't have been there.
And we heard the guy say to the chick, what if one of these fucking kids are these?
What are we going to do?
Roll them up like rug and throw them in the thing.
And, you know, we just left because it was like, we got it.
We understood we shouldn't have been there.
You know, I mean.
So how does it skew your view of adults as you then get that do you ever what what
would you how would you say they were because you said they had kids they were probably in their
late 20s or early 30s and i was maybe 13 or 14 i was in eighth grade uh it was the year was 1999
i remember that i remember that uh new year's 1998 99 uh they were living in my town in the mayor's son, a house the mayor's son was renting or whatever.
There was maybe three to four rooms in the house, and every family had a room.
That's how you knew it was kind of a cracker.
It was like one room was two people.
The other room was a woman and her three kids.
The other room, and then everybody at the house,
and some guy slept on the couch,
and everybody at the house would do drugs. I say crack house, but it was mostly cocaine,
and there was a lot of weed, and there was drinking.
I think some people were doing crack.
We weren't doing crack, but it was a drug house.
There was drugs being sold.
There were deals being made.
There were people getting in and out of jail. It was just one of those houses where if you wanted to
purchase drugs in my town and here's the thing we were 13 14 we had nowhere to go with you know and
it was cold it's it's long island it's december well it's december it's freezing right so in the
fall yeah sure it's fun to walk around outside in the spring.
But in the dead of winter, you got to go somewhere.
So we found this place and the people, they were very welcoming and hospitable to us.
And we would buy weed there and cocaine there and do it there with them.
And you just kind of like have fun and meet people.
And it was kind of like a teen night for me and my friend.
And it was, again, you know, it was not, you know, my parents, they didn't know we were
doing this.
They thought we were like walking around.
My parents are boomers.
And with all due respect, you know, no generation has cared less about their children than Boop.
They just, it wasn't, raising us wasn't part of the thing.
For most of the boomer generation,
they just didn't, they would go,
here's some Wendy's, now go get molested.
They didn't really, that's just what it was.
They didn't really concern themselves.
It was all about them.
It was all about them.
So they would just feed us poison.
Feed us poison.
Let's go to Pizza Hut.
Here's a big pizza.
And then go walk around our town for five hours.
Figure something out.
God only knows what they thought we were doing.
But we were, you know, we were in a crack.
I mean, they didn't know we were in a crack house.
They thought we were, like, hanging out in the schoolyard or something.
And we were, like, you know, we were just hanging out with these people.
But what it showed me was that adults weren't always authority figures,
which I kind of knew.
So that was a big thing, right?
Learning about this, I was like, adults aren't authority figures. authority figures and then i also saw like there were kids around the house i'm like fuck how are these kids gonna have any shot at life
being raised in this type of environment and then i also not to get political but i was like
what could you do like as a government what could you do for these people?
Now, I'm sure there are things you could do.
But, like, I was always skeptical because then I would hear, like, I would go to, like, you know, get in high school and college or whatever.
And people would be like, here's how to fix poverty.
Here's how to fix this.
And I'm like, but you don't know anything because you've never been.
Right.
So you have no idea.
You're just looking.
I get that you
know so i was always like yeah it's it's deeply complex these issues or there's a lot of a lot
of issues that intersect and and make it very hard i think not that i'm not saying the government
shouldn't do more for people they should but it's very difficult to pinpoint exactly what needs to
be done because these cases are very complex.
You have a lot of people with bad or no jobs, very little education, really addicted to drugs.
The only way they're making money is selling drugs. You have kids being raised in that type
of environment. What can you do to truly break that cycle? It's very difficult.
Well, what finally got you out of there?
truly break that cycle, it's very difficult.
Well, what finally got you out of there?
So my parents, I was living with my mother.
My parents got divorced in, they got divorced in sixth, seventh grade.
Now they announced they were going to get divorced in fifth grade, but then they didn't have the money to get divorced.
So they brought in a mediator.
They didn't have the money for lawyers.
They brought in a mediator who would sit at my dining room table and divide up all of their spoils.
Do you remember this?
Yes.
All of the things that they would have a big.
The toaster oven.
Yeah, the Beanie Babies, the collections of McDonald's toys.
For real.
The lamp.
Oh, yeah.
That's right, because your mom would.
My mother would.
That's right.
You told that story about her yelling. And get McDonald's toys and beanie babies and hess trucks and everything you know
so they would divide their their estate i guess is the term
the mediator would i'm getting all the hess trucks yeah yeah so my father like uh you know
my dad and her divided up whatever i think she took most of that and he got a lamp or whatever
and it was two years it was hellish you know in terms of like they again they just weren't My dad and her divided up whatever. I think she took most of that, and he got a lamp or whatever.
And it was two years, and it was hellish in terms of like, again, they just weren't concerned with being parents.
I love both of them.
They weren't concerned with parenting.
Well, obviously, your mom had something going on for quite a while.
She had something going on, and she was a schizophrenic.
And even worse than that, my father was in a band.
So it's like, what are you going to do?
So, again, they were going to.
I mean, you've got to remember, this was a generation of people that were like, they were at Woodstock.
And then 10 years later, my dad was selling office equipment.
Like, what the fuck happened?
He didn't know what happened.
So I get it. I mean, my mother got married in a puka shell necklace.
And he had a powder blue suit on.
And they got married on a beach.
And then years later, Reagan's in office. And they're fucking trying to figure out what a home equity loan is so they were like i get it i get how how much it all turned okay i'm well aware
i have how much it all this is what happened so they finally got divorced and then i live with mom for two years and then as
i live with mom i drugged it up i was i was my dad was gone my mother was gone out of state or
just living with his brother in jersey i was trying to figure out how to become a person
sexuality was weird because then i was like oh i kind of don't like girls like the way all my
friends do whatever uh i hadn't you know because when you're in seventh grade, eighth grade,
that stuff starts to. Yeah. So then the drugs became a thing to like medicate and kill those
thoughts. And then also I was unsupervised because I had my grandmother was really trying to watch me
and my buddy. If anybody's trying to govern a teenager you know
you just you're you're out you're doing things you're and what happened was i started to kind
of spiral so a decision was made to have me go live with my father in ninth grade because your
mom at this point she can't hold a job she can't she's starting to have a real problem with holding
a job it's you know it's very tough for her to hold a job because she'll swim though
right she can still swim she's talking about people that are following her she's talking
about all these things that's what i would always also my mother i don't know how much i got into
this my mother to keep her house long island rents the house out did i go into this i don't remember
okay like she lets people come in she rents rooms out in the house
and who is renting rooms in houses crack drug dealers so they move into my house and by the way
if you've ever had your mother rent rooms to cocaine dealers when you're in eighth grade, you know how convenient it is.
It's just easy.
It's so convenient to buy cocaine at breakfast, which was what I was doing.
I was watching a drug dealer flip pancakes, and then we would do lines.
But it was a good time.
That's what you always say. It was a good time. That's what you always say.
It was a good time.
I hear you.
If it was all bad, I would tell you drugs work.
Cigarettes work.
Cigarettes are like $90.
The package is like, it kills you.
No one cares.
It just, so the drugs don't work forever,
and there's other things you should do instead of them.
But, I mean, this was an era.
But are these people you know of?
Yes, I know them from my town.
I know them from my town.
I remember hanging out in my town one day and some guy going,
we're going to buy an ounce of weed.
We're going to 269 Madison Avenue, which is where I used to live.
And I'm like, can I get a ride with you?
And they're like, are you buying something there?
I said, I live there.
And they're like, really? I was like, can I get a ride with you? And they're like, are you buying something there? I said, I live there. And they're like, really?
I was like, yeah.
I would walk into a house and see my mother and big drug dealers from my town.
I mean, not the Sinaloa cartel, but big for Long Island.
Yeah, right.
Eating baked clams.
And this was the time of really great baked clams.
Really good, really good Long Island seafood.
And I would walk in and be like, hi, mom. Hi, drug dealer I've known for a long time. Eating baked clams. Really good, really good Long Island seafood. And I would walk in and be like,
hi, mom. Hi, drug dealer. I've known for a long time eating baked clams. You know,
she rented a room to a guy named Dennis, who is not a drug dealer, but he was he loved to drink.
And in my show, The Tim Dillon Show, I've told the story a bunch and it's become like the de facto
saying of my show Life in the Big City, because Dennis, no matter
what you said to Dennis, he would just go, Life in the Big City.
And like my mother said to him once, you know, your kids haven't spoken to you in five years.
They called the other day.
You were drunk and you answered the phone drunk and they hung up and now they don't
want to speak to you ever again.
And Dennis would go, he would have a Burger King cup with wine in it and i wine and marlboro
reds and he would go life in the big city you know my mother would go the house is going to
be foreclosed on you're going to be homeless life in the big city he lived in her van for six months
after six months six months after and he would say to us he'd go hey i'm living in a van that's
life in the big city.
What was great about this, I'm pretty sure Dennis had never been to a city.
He'd never, other than like Vietnam or wherever he went.
But that's not a city, but you know what I mean?
Like I think that might have been the biggest city he'd been to.
But he had a great attitude about the trials and tribulations of life,
the waves that hit us all.
He would say, life in the big city.
Oh, you lost your job.
Life in the big city.
Your brother hates you because he's accusing you of stealing his money.
Life in the big city.
He was a great, like I appreciated the way he just kind of breezed through it all, you know? It really is a way to go.
And he died, as most people that are like him do, shark fishing in Montauk.
He just clutched his heart one day on the boat, and it was over.
And these are the things.
These are the stories.
But so...
So wait, I'll be...
Yeah, it's A3.
So many goddamn questions here.
Is your mom also using at the time?
No, she's not a druggie.
She's really not.
And she kind of knows that they are doing something.
Does she know you're using from them?
She knows that I'm smoking pot.
She doesn't know that I'm buying it there.
She has an inkling that I'm smoking pot,
but she's also schizophrenic.
So she's all over the place.
Like, I remember one time we had dropped acid from the guy upstairs,
and she was screaming, what's wrong with your eyes?
I can't believe, what is wrong with you?
And then she just started screaming, I can't believe I'm with all these drug addicts,
drug addicts, alcoholics, drug addicts.
And Dennis just opened his door and said, Patty, it's just acid.
Shut the fuck up.
He goes, you'd ruin anyone's trip.
Get the fuck in your room.
And I went, this guy really is an advocate of mine.
And it was just, you know, she was not happy that I was using drugs.
She was angry about it.
But she was trying to save her house, and she rented rooms to these people.
Did it work that she saved the house?
No, no.
Did it work?
Yes, Ryan.
It all turned out just fine.
All the drug addicts and her, they all live happily ever after.
What a great question.
Did it work?
Oh, yes, it worked.
Didn't it sound like it was working?
How long did it work?
It worked two years.
That's a minute.
Anything can really work for two years.
So she basically...
So she...
Sorry, I had to text.
That's one of the drug dealers.
She... No, I'm kidding. She tried's one of the drug dealers. She, no, I'm kidding.
She tried to hold on to this house.
I still remember, you know, being in eighth grade, living in this house.
How many bedrooms?
What does this house look like?
Three upstairs.
Three upstairs.
One downstairs.
You, her, and then she'd rent those two?
She had one room downstairs. Dennis had a room downstairs. I had a room upstairs, and then she'd rent those two? She had one room downstairs.
Dennis had a room downstairs.
I had a room upstairs.
And then she rented two upstairs.
Two, okay.
And then there was another little room downstairs.
And then eventually I went downstairs and she rented that third room.
She rented to a woman named Michelle once who was just a fun, just a fun.
You know, there are people that are just fun.
They're just fun. You know, there are people that are just fun. They're just fun.
And we would, this woman had an old Lincoln Town car.
And we used to just, me and my friend would just get in her car and we'd blast lines of coke and smoke cigarettes.
And she would just drive around our town.
While you're doing the coke and smoking cigarettes?
Yeah, this woman, Michelle.
And we would drive around.
We would all do coke.
I was like 13, 14. And we would drive around. We would all do coke. I was like 13, 14.
And we'd all drive around the town.
And she would just be like,
these people are real white trash.
And I'm like, yeah, fuck those people.
They're real trash.
And she was just fun.
Again, she was a wild lady.
She was fun.
I think that, I don't know what happened to her.
I don't know what happened to a lot of these people.
They actually all survived.
They're all kind of fine.
That's amazing.
They do.
You know who dies?
Like good people.
You're right.
That's really the reality.
You're right.
Good people get brain cancer.
Bad people are like roaches.
Bad people are just around.
So I think it was a decision made by my mother and my father that we got to get him out of
this environment and he's got to go live with my dad.
So I went to my dad and I went and moved in with my dad in ninth grade and I went to Catholic school and I found out that
nobody in Catholic school did drugs. And then I sobered up and then everything was fine. Kidding.
I was going to say, yeah. I found out that drugs are actually better in big backyards
with swimming pools and people at Lexuses. It was great.
And then I learned about my love of real estate.
You know, I love property.
And I didn't know that until I met really rich kids
I could do cocaine with in Catholic school.
So my parents introducing me to a better class of drug addict
was very smart of them, you know, long term.
So that's when I moved in with my dad
and I went to Holy Trinity Diocese in high school.
It was a hip Catholic school like the teachers would make out with the kids.
I'm kidding, but that did happen twice.
That did happen twice.
Two times?
Two times.
Not to me, to the hot kids.
We get it.
But so it was.
Did they get caught?
Yeah.
Yeah.
It was a thing.
People got fired.
It was a problem.
Did you have women, female teachers, or was it all boy school, all male teachers?
No, it was a co-ed, racially diverse school in Hicksville, Long Island,
right by the Village Green where Billy Joel wrote that song.
You remember those days, hanging out by the Village Green?
And it was as Long Island as you could get.
as long island as you could get like it was just it was pretty uh i would say middle solidly middle class with a sprinkling of wealthy kids solidly middle class again for long island that might not
be the middle class for kansas but middle class meeting that you know my friends lived in levitt
houses you know it and a few kids had sprawling, you know, big,
one kid lived next to Vinny Testaverde, like some people had, but pretty much it was a
somewhat middle class school.
It wasn't a prep school.
It wasn't a bunch of rich kids, but there were a few of them.
And it was, you know, it was where I spent four years of high school.
And at that point I started to transition and, you because I wasn't so what I did was like I
stopped when I moved with my dad I you know during ninth grade I was still doing blow
and during a little bit of 10th grade but then I started to just kind of I phased out of that
and I phased into just kind of drinking.
I found drinking in 11th grade because that was what everybody else was doing.
Cocaine before drinking.
Cocaine before drinking, which is my family crest.
Low before liquor.
But what happened was I wanted to fit in with these kids.
So what happened was I wanted to fit in with these kids, which means that I, whatchamacallit, that I wanted to do what they were doing.
I wanted to do what they were doing.
And what were they drinking?
What was back then?
Whiskey?
Yeah, anything we could get our hands on.
I mean, I was never a beer drinker.
I never drank anything with bubbles.
So I always drank like hard liquor.
I hate carbonation.
I drink, don't drink soda.
I don't do any of that.
So in 11th grade, I was like,
I want to drink and smoke pot
or whatever these kids are doing.
So I want to fit in with them
and I don't want to hang out with these,
you know, and by that time,
that house had been broken up.
They'd all moved upstate, you know.
And what about dating in high school for you?
I mean, no real dating.
I mean, I would hook up with girls because that was what I was trying to do.
I was trying to be straight.
So I would hook up with girls, but it wasn't like, it was kind of to show off.
But you were trying to be straight for who?
For everybody.
I mean, it was a Long Island Catholic school.
It was 2002.
I mean, it was just a different time.
Now kids are like gay at four.
They're like trans at seven.
They're leading a march at nine. Leading a march?
It's not. It's not. You know, it's different.
It's different now.
Now people aren't even gay. People are like,
I'm a gender. And you're like, you're not even gay.
But they don't care. It's like, they're like,
but on Instagram it says I am. It's like, whatever.
So now people are just like, whatever
identity will do, you know, as long as I don't have
to have a personality. So you're worried about the image at the time or being bullied or all of it.
Well, all of it.
I wanted friends.
And I didn't think I would have friends if I was like, you know, and I also.
Did you have any other gay friends at the time?
Was anyone?
No one was out at all.
Or at least quietly to each other.
There were people that were out in high school.
There were.
And I was fine with them.
Like, I wasn't. But I don't think I wasn't friendly with them.
I was a popular kid.
I tried to be popular.
And I got nominated for Homecoming King.
In the beginning of high school, I wasn't popular.
But then I tried to be popular because I wanted to be popular.
And I wanted people to like me.
So I got nominated for Homecoming King in senior year and became a popular person, whatever the hell that means.
I went to parties and all that bullshit.
So that was more important to me than living an honest life you know still is you don't live in la you know so the thing is i yeah i mean if i come out of the closet earlier
i would have went to a liberal arts college and been happier and not funny and i wouldn't do this
for a living uh maybe i would have been able to control my drug use whatever i'd be like all the other gay comics
who'd suck i'm kidding i'm kidding they're great um i'm kidding it's a joke um but uh yeah it's
when i look back i go yeah there were kids who were out so i always say like i don't blame the who were out. So I always say, like, I don't blame the environment.
I could have been stronger.
I could have been more.
I don't blame the environment.
I try not to blame environments for things, even though that's the rage.
I try not to blame anyone.
It was all about me because I wanted to just be this popular kid.
I could have came out of the closet and had, like, three friends that are, like,
these are my diehard friends.
I wanted to be popular and, you know. So that was more important use my diehard friends. I want it to be popular. And you know,
so that was more important to me than being true.
So you have a lot going on.
There's a lot going on.
There's a lot going on.
Parents,
your parents,
turmoil,
all inner turmoil.
Like I felt like a lot of the problem with,
um,
it's hard.
I think for certain gay people that don't identify, like, they're
not the stereotype of what a gay person is.
So it's hard for them because they're like, well, I don't fit in here, but I kind of don't
fit in there either.
So it's like, you're in this weird place.
And there's a lot of people I know now that are either more private about it or they're
not like, they're just whatever, like, they're just like, hey, I live my life.
I do what I want.
I don't, because now there's this agenda of all these things you have to agree with and i don't think there's a lot of gay people that do agree with all of those things like now
it's like uh men and women don't exist and you're like whoa wait a minute well that that actually
flies in the face of gay because if like if you're if you're attracted to dudes and there's a woman
who goes well identifies a dude you go well you can identify as whatever you want but to me you're attracted to dudes and there's a woman who goes, well, identify as a dude. You go, well, you can identify as whatever you want.
But to me, you're a woman.
So it's this weird contradictory space now where I think a lot of people are kind of, it's confusing.
Everything is very confusing now.
But back then, I think it was just the same.
It was just motivated by fear and not wanting to be uncool.
So did you have a girlfriend through high school?
I would go out with people.
I mean, it wasn't like a solid.
There was a girl that I liked who was very fun to hang out with
who's still a friend of mine.
I mean, I would just try to make out with the girl at a party
and have everybody be like, yeah, how cool is that?
Well, you told the story about the guy you had met online.
Yeah, I met a guy.
Was that your first experience? Yeah, I think so think so yeah 100 so when what age was that again and you don't have to tell
that whole story again first year of college uh it was just a firefighter that i met in a hotel
room in brooklyn and he wasn't really a firefighter he was like he was in a firefighter training
program or something it was after 9-11 um he was like oh yeah. He was like, oh yeah, I'm going to say it. You know, I was,
you know,
and then he said he learned
he was gay during a trip to Italy
or whatever.
And I'm like,
but he was like a Guido guy.
He was like,
oh yeah,
I went to Italy.
But he kept saying,
I'm not gay.
I went to Italy.
Yeah,
he kept saying,
I'm not gay.
I'm not gay.
You know,
which if you blow somebody
and they keep saying that,
you have to keep looking up
and going,
no,
I know,
I know.
It's awful.
It's very strange.
It's like an odd, it's an odd interaction to have to keep looking up and going, no, I know, I know. It's awesome. It's very strange. It's like an odd interaction to have.
To be like, yeah.
Oh, me neither.
No, I believe you.
I believe you.
This is a joke.
He was not that bright.
He said when we checked into the hotel, he says to the guy behind the thing,
he's like, yo, we're not smoking crack in here or nothing.
And I'm like, well, why would you say that?
He's like, I don't want people thinking we're smoking crack.
I'm like, that's the best case thing people are thinking about it
that's our great cover story we should literally go buy crack right now and light it on fire in
the corner of the room what is wrong with you but i haven't seen him since but i hope he's doing well
probably not probably on facebook somewhere yeah they're all on facebook they're all on facebook
look up anyone that you think is dead they They're on Facebook. There's memorial pages on Facebook that comment.
Oh, really?
Yeah.
I go, that guy's dead, and he comments.
And I'm like, what?
It's like Tommy's memorial.
But he's still there.
Tommy's memorial likes your picture of an omelet.
It's like, God, Tommy's commitment to breakfast is wild.
From the beyond.
So when do you start dating guys regularly when do you i mean i don't know
if i'm dating anyone ever regularly i mean after that experience you stopped seeing women
yeah or no no yes i'm trying to think i was still dating but i wasn't like i think i was
going out with dudes in in in you know after college i came out of the closet at 25.
Okay, 25.
I'm 34 now, so I came out at 25.
So it was very late.
So you're 12 years younger.
You're a baby.
So you had internet.
And that's what people, when they see me, they think that.
They go, baby.
I had internet, yes.
So is that how you're meeting men, or are you meeting them in your-
Craigslist.
I would meet dudes on Craigslist.
I think I went to community college i met a guy there but still it was very like i was still very inhibited
about it it wasn't a big part of my life it wasn't like i think it's hard to imagine now because
things have changed so much and have been so progressive but now it really is like a different
world um from where you know it was then so i was kind of Even if you were out and comfortable and everything back then,
it's still a different world in these last 10, 15 years.
Yeah, 100%. So I would meet people, but I wasn't introducing anyone to my parents.
And then I came out at 25. To your parents as well? To my parents, yeah. My mom was like,
I want grandchildren. And I'm like, yeah, that's what you need. I'm like, back in the cage.
And then.
And.
Oh, my God.
And then my dad, my dad, typical boomer, who was like, just make sure you take time to golf, son.
You know, or something.
Just drop that in.
As long as he just didn't have to work more hours, I don't think it bothered him.
But it's, you know, it wasn't like, and I told my friends, none of them cared.
So that's what I wanted to ask you.
Was there this buildup of like, oh, my God, I'm about to tell my parents.
Yeah, no one cared.
And there's a few people I'm not close with now, but I don't think it has anything to do with that.
You just move on and you lose friends.
But I don't think it really mattered to do with that. You just move on and you lose friends. But I don't think it really mattered to anyone.
It mattered more to you, obviously.
I think it mattered to one of my friends who I was close with
but then was just a weird guy anyway
and just married a Russian woman at City Hall or something.
So he was on his journey of strange things.
I was going to say, yeah.
Yeah, so I don't know where he is.
I think it mattered maybe to one person.
I don't think it really mattered to anyone else.
No one cared.
From what I remember, no one cared.
You know?
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Now let's get back into the do.
So after, where'd you go to college again?
Nassau Community College, where success starts and continues.
Is that their motto?
Yeah, it is their motto.
It's one of the top community colleges in the country
by the Cheesecake Factory in Long Island.
And to say that people are unmotivated at Nassau Community College
really doesn't even begin to describe the level of human filth and trash.
I mean, I'm talking about Long Island girls in like terry cloth sweatpants in flip flops on their razor phones,
screaming at their boyfriends in class, lighting cigarettes right outside the window,
blasting music, you know, not doing anything.
And that's where I met my friend Kenny, who was doing,
he had a Range Rover and he had spiky hair.
And he goes, listen, I sell fucking mortgages.
He was my debate partner.
He goes, you're a good talker.
You should just start selling mortgages.
He goes, fuck this place.
And I'm like, buddy, I'm ahead of you.
Fuck this place.
And he's like, we're going to sell mortgages.
It's this great business.
There's so much money out there for people trying to buy houses.
And everybody's getting rich.
And you should just hang out with rich people.
So I'm like, I should hang out with rich people.
And then I won't have to come out of the closet.
I won't have to do anything.
I'll just be rich enough where I can do what I want.
And I'm going to get rich selling mortgages on Long Island. And that was my goal. And that's when I transitioned from a college
kid to a 45-year-old mortgage broker with a drinking problem who had tax liens.
That was when I left. That was your shift.
I left childhood.
And if people listen to the old episode, I was a child actor.
So it's like I really left it when I was six years old and I started acting.
But when I really look back and I said, oh, I left childhood,
it was like I left when I left college.
And I just went into the world of mortgage guys in Long Island.
It was like, well now any any hint of a
college experience or going away or being a kid or having any regular college age stuff didn't happen
so then i went to um into the mortgage world and started making bank though right i started
making some decent money you know especially for a kid that kid that age. In your mid-20s?
Mid-20s.
I bought a house.
I had no money, but I still bought a house for $600,000 because I'm, like, fucking badass.
And that was foreclosed on and taken.
But, you know, what I learned from that is that I really just had the balls to make it happen, as Gary Vee would say.
So I took his advice, and I just hustled and grinded, and I bought a home.
And then right after I bought a home – and again, people don't understand the mortgage thing.
People think that we were all like – everybody thinks we're like boiler room, like we knew that it was all going to – nobody knew that.
I was giving cards out to my family.
I took one of these mortgages.
At the end of the day, there was pred predatory lending there was bad stuff going on but a lot
of people you know america is not a i hate to break it to everybody i know america is not a
country of victims it's a country of criminals and it's a country of of people that are have
varying degrees of success it starts from the boston tea party and then everybody would send
their degenerates
to the americans that's who we are victims of the subprime mortgage crisis going back to talk to
like victims of other things like the holocaust or anything right like oh what was done to you
they were like i was given 200 grand i didn't deserve what yeah yeah you you misrepresented
how much money you made you got a bigger loan loan than you deserved. And it's like,
yeah, there was predatory lending. Some of it was, I guess, racial. I'm sure there was horrible
shit that went on. But to me, I was selling mortgages to people that lived in Long Island
that wanted man caves and pools. You know, that's the reality. You know, I remember going to
a house in the Bronx that was right next to Montefiore Medical Center.
It was an older white couple that were very tan and they had like a fly strip in their house and there were flies collect.
And they were like, we want to refinance it.
Like Montefiore Medical Center is going to buy this house.
We're going to be a million.
And Montefiore kept offering them to buy the house.
Offering them, offering them, offering. And they were like,
we're not budging until it's over a million. And they were offering
the $800,000. I said, take it. What's the difference
between, because I had done a loan for them. And I go,
what's the difference between $800,000? Just take it.
You have nothing. And they waited.
The Montefiore
Medical Center just decided, you know what, we're going to expand
the hospital in the other direction. And said,
fuck those people. Wow.
And it was crazy um and then they and
and those people so it's like greed is just we all have it and people can facilitate like
it was just i bumped into so many cases of people that were just like i want more i deserve more
and can you help me get more i bought a house at 22 for no goddamn reason
you know and it it went bad because i bought it in 2006 at the height of the market and the market
literally crashed in 2007 and i stayed in the business till 2010 i mean really oh yeah you're
still able to sell after that no but i was still able to go to an office, you know, hung over and, you know, call people and go,
Hi, this is Tim Dillon with Capstar Mortgage.
Are you interested in, you know, have you?
And then people would be like, shut up.
You people are the worst people.
And I was like, all right.
It was a sad office.
There was like nine guys still left in the business.
We're in an office.
It was windowless.
We were in Melville, Long Island, which is the mortgage corridor.
It's where all these big banks were.
But now all these banks have gone out of business.
All the Range Rovers and Beamers were out of the parking lots.
The parking lots were empty.
I mean, literally, it would be like tumbleweeds like blowing through.
It was like life after people.
It was just post-apocalyptic hellscape.
And I was in this office with nine other desperate people sitting there with
leaks. It was leaking. There was like fruit flies. The heat didn't work. And we were all trying to
sell a product that nobody, everybody kind of needed, but nobody qualified for. And it was,
the year was 2009 and it was very depressing. And we were having sales meetings at Taco Bell
because nobody had money and people's mothers were dropping them off to work. It was insane. It was insanely depressing. And people
would just stand in the parking lot and smoke cigarettes all day and talk about, you know,
conspiracies and people would come into the office and they would be like, you know, I think Obama
is in Al Qaeda. And I'd be like, well, I don't know about that. But who knows?
Could be.
And it was just this really depressing time.
And it was the saddest.
A sales guy is supposed to have money, confidence.
We had none of that left.
We had been broken, beaten down and broken.
And the dude who was kind of the head of the operation was this drunk named Bob.
Bob had lost his license for Dewey, so we had to take turns driving him home.
He was our boss.
Everyone had to just take shifts.
Yeah, and you have to drive your bike.
And he would fall asleep because you drink all day at Chili's.
And then he'd fall asleep on the way home in your car and then wake up at a stoplight to just deliver a cryptic message.
He'd be like, and then he'd wake up and go,
we're in big trouble, I'll tell you that much, we're in big trouble.
And you'd go, what?
And then he'd go, no, no, make a left at Park Avenue.
And so he would just deliver these cryptic messages.
This is how that company started.
You want to hear how that company started?
I pitched this as a show and nobody bought it.
Are they fucking nuts, Sickler?
Yeah.
So here's what happened.
This is how the company started.
This guy, Bob, was a high-level guy
and a major mortgage lender in Long Island.
He's a CFO.
He sees that this company is going to kind of crumble.
He sees the writing on the wall.
It's like, we're in trouble.
We're holding on to a lot of bad debt.
This thing is just going to go.
It's going left.
We got to get out.
So he pulls his buddy.
His buddy and him, instead of evacuating the business, right?
This is such a Long Island fucking thing.
They go, we're going to do it the right way.
We have all this know-how.
We're going to put together a small company.
We're going to do it the right way. We have all this know-how. We're going to put together a small company. We're going to do it the right way. So they go up to this guy's house upstate,
which is partially done. They're getting sauced. They're talking about the new company they're
going to have. Whoever this other guy is, I don't know, falls through a second floor that's not
completely done and dies. No. Dies. Come on.
While they're up there talking about this shit?
Instead of abandoning the project, Bob then walks around at his funeral and goes,
I just want to let you know I'm going to open the company for your father.
He was a good man.
He believed in tight lending standards.
We're going to open this company.
The underwriting, it was cruel.
At the funeral?
The company started in death. was the company started in death yeah it started in death and so
i worked there for about a year and a half um very sad christmas party very very sad very sad
i think we all got like a hero from a pizzeria and cut it like six ways and nibbled on it
and then just and i was still boozing it up boozing it hard boozing it like six ways and nibbled on it. And I was still boozing it up, boozing it hard, boozing it hard, boozing.
And where are you living, in the house?
I'm living in my foreclosed home.
And I've rented it to a family who lives upstairs,
and I've also rented it to one of my mother's friends that she met
in a mental institution.
We call him Derelict Phil.
Okay.
Derelict Phil was a lounge singer from Vegas who never took off.
My mother met him in the hatch, the booby hatch,
and she goes, they're letting Phil out. And Phil needs a place to live. So I said he can rent one
of the rooms downstairs. So I would come home and Phil would be playing Mac the Knife on a keyboard,
like a Casio keyboard. He'd be like, Mac the Knife. And then upstairs, I rented it too. They
were like ministers. It was like a nice black family. They were like ministers, and they were fine.
They just were, you know, like they were just religious people.
So they lived upstairs.
Darlick Phil lived downstairs.
I was sleeping on a couch at this point downstairs,
working this horrible thing, waiting for it all to come crashing down.
At this point, I have a boating accident with my friend's father bud he's so fun he's so much
fun I got in two boating accidents with him what do you mean well he's just a fun guy like he'd
never worked and I think he might have sold drugs but he's literally never worked and we just did
my friend lived in this little house in Freeport Long Island and we used to have the craziest
parties there and like uh his father would steal like his father stole a flame throwing statue from
someone else's yard and just brought it back to a party one day um he would shoot he would have a
paint the father would have a paintball gun and just shoot beers out of people's hands it was
fun he was just like yeah that guy you know and he then had this little boat and take people out
on the boat i would go out on the boat with him and we'd have a lot of fun. We'd get hammered and you just drive around the boat.
And then so we want the first time we crashed, we ran up on a marsh, a marsh.
And it was like fast.
I got thrown out of the boat.
Could have been paralyzed.
Could have been killed.
The second time we just crashed into the piling of a bridge.
Jesus.
That's when he looked at me.
He goes, you got to stop hanging out with me.
I'm trying to kill myself.
Oh, I was like, this is negative. He said that to me. He goes, you got to stop hanging out with me i'm trying to kill myself oh i was like this is real negative
he said that to me because you gotta stop hanging out with me because i'm really trying to kill
myself i was like oh okay i just smoked a cigarette bloody from the edge yeah that's
that ain't great and he uh he so
he has liver cancer now.
Walked into the doctor and went, I'll do anything, but I ain't stopping drinking.
He's just fun.
He's just fun.
A lot of fun.
So at that point, I started saying to myself, this is becoming a real booze.
And being a junk box is becoming a real problem.
I'm not really doing cocaine anymore, but I'm just drinking.
I haven't done coke in years.
And what is your drink of choice at this point?
A martini, a Beefeater martini. it's pretty much the highest proof alcohol behind the bar it's big
you know it's a beast of a drink 80 proof and you drink four or five of them you get or kettle one
on the rocks i always want hard liquor on the rocks or straight up martini you like clear liquor
clear liquor and that because of the figure no and then do shots and then and then i would do
shots also on top of that i would do shots on top of it yeah
because i was like i i don't know if you've listened to the rest of the episode but i had
problems yeah i was like you're running from something so at that point i was sitting in my
office and i was really really hammered and not really hammered that day. I was hungover, but I'd been consistently drinking.
I had gotten...
It was like the foreclosure notices kept coming in.
It kept coming in.
The bills kept coming in.
I'm not paying anything.
I'm not paying taxes.
I'm not paying anything.
I just have no money, and I'm closing a deal once every three months.
There's just no money, no money, no money, no money.
And so eventually, I get a summons for
jury duty and i i was like i gotta go answer this summons because they'll put you in jail right
and i got one of the red one yeah which is what you haven't answered it i just kept ignoring them
and ignoring them ignoring them and then i got one that that basically was like you need to get
your fucking ass down here and then when i I was, never forget, I went down.
It was a black lady behind the counter.
When I handed it, she goes, got one of those, huh?
And I was like, is that bad?
She's like.
Yeah, that's horrible.
But my argument was, this is a summons.
It is not a subpoena.
I don't know why.
A summons is a suggestion that we'd like you to come to court.
You don't have to.
But subpoenas, you better have your fucking ass there.
And she goes, look, you're not wrong, but good luck arguing
that. And then I got stuck on a
five fucking week
drug case. Oh, interesting.
Five weeks. The last week of January
all the way through February.
Interesting. What was it, like drugs?
It was these two gangbangers that
had, I mean, done
a drug deal in the Jack in the Box
parking lot in a Toyota fucking
minivan. Jack in the Box, by the way, not good.
Keep going. Yeah. And
millions in cash, millions in
drugs, automatic
weapons in the washer and dryer in their
apartment. Like, it was, they had
phone, everything. They had it all.
It was, I don't even know why we needed to do
this for five weeks, but what they did, the defend defendants did was the old school mafia shit because back then
they would say well where you have you had to say your fucking name yeah and where you lived and
everybody would just say los angeles yeah but where when why do i have to say where you need
to say encino now now you've given us a specific one somebody. And the old school mafia trick is for them to look at you like this,
and then they just write shit.
While you're talking, they're just looking.
You say, oh, I'm Ryan Sickler, and I live in San Diego.
And they write and stare.
And it intimidated the fuck out of our jury.
And those ladies got worried.
And then courts opened.
So they would have their fucking gangbanger friends with
face tats and everything just come and fill the seats and just stare at us the whole time we were
fucking scared what happened they were so guilty that's what i'm saying it was they had everything
from them admitting it yeah they got it we had to well i you think that's cool i had murder torture
rape that for how yeah i did murder torture rape j rape. Yeah, I had murder, torture, rape. Jesus.
Yeah, okay?
We did it within two weeks, too, okay?
So we don't need a five-week drug case.
Five weeks of no pay.
We had murder, torture.
We had a civil suit to the cops because this guy was a rat.
He was an informant.
Jeez, that's a good one.
They kept letting him out of jail, and he murdered this chick,
and it was very bad.
At least I think he did. I didn't listen. I didn't listen that closely, but he a good one. They kept letting him out of jail, and he murdered this chick, and it was very bad. At least I think he did.
I didn't listen.
I didn't listen that closely, but he had weird eyes.
The point is, no, I was so excited.
I tried to get jury duty.
As soon as I went there and heard it was murder and torture,
I was like, I got to get on this.
I need something in my life.
I can't afford to go to a retreat.
A retreat.
I need this.
And then they were like, oh, the DA's like, your license has been suspended.
Don't you hate the cops?
I'm like, no, I hate myself for not being responsible.
She's like, okay.
And the defense attorney was like, you know,
they ask you the jury selection.
Then she's like, murder, torture, how can you be impartial?
And I'm like, those are just words.
I've seen no evidence.
Words mean nothing.
And I found out later I was a defense pick.
Like the defense looked at me and were like,
he'll understand torture, you know?
He'll get it. He'll get get it sometimes you have a day you know i wasn't like a law and order pick i was like a defense pick yeah like yeah we want that guy we want that guy
he's a scumbag think about what people have to think about you yes pick is on a murder torture
rape defense side they literally looked at went, he's a piece of shit.
That guy would have done this crime.
He might have done this crime.
So that was an intense experience because you hear about mortality every fucking day.
At the end of that experience, I was like, oh, I got to really get out of the job I'm in.
I got to sober up. I should be honest, come out of the closet, and then like, oh, I got to really get out of the job I'm in. I got to sober up.
I should be honest, come out of the closet.
And then I should do something I like with my life.
And this is all at 25?
This is all at 25.
And the trial ended.
It was the spring of 2010.
And then I went through that summer.
I had one more summer of boozing it up and whatever, soft shell crabs, whatever the fuck I was doing.
And then I sobered up in the late summer and then I started
standup comedy, I think in late August or first week of September. I can't remember. I think late
August. And I started, I did my first set in a coffee house tattoo parlor, Long Island. And,
uh, that was my first set. And I was in AA and I brought some of my AA people to watch me do my first set.
And at that point, it was the fall of 2010.
Within two weeks, three weeks, I was driving into the city.
Within two to three years, I was living in New York City.
Five to six years after that, I had done JFL.
I had done a Comedy Central special.
I had done one of the Netflix specials.
I moved out to Los Angeles.
I started coming out here heavily about two years ago, And then I moved out here about a year ago. So that started that whole journey, but my life was going in this
direction. And then that, that murder trial kind of just, now I might've gotten there in another
way, another time, another place, but that crystallized a lot of things in my head like fuck i gotta
just move on from this because otherwise you know and one of the guys in the jury was like you should
try stand-up comedy and i always thought i was funny i always wanted to kind of be a comedian
or kind of be in that world you hadn't even dabbled yet had dabbled had i think i did one
open mic that didn't work out great in New York City before that whole thing.
I think I drove in once a year prior to that.
No, I know I did.
I just can't.
I wish I could identify what mic it was.
But I drove into New York City.
I did one mic and it didn't really work.
I didn't really do it after that until this trial happened.
And it was still in like that 2008, 2009 crazy mortgage time.
I drove into the city, tried one mic.
still in like that 2008 2009 crazy mortgage time i drove into the city tried one mic and then coming into comedy 25 now having some of a comedic voice and some stories and some perspective to
draw on i just hit the ground running i started to do a comedy all the time and that was then it's
just you know that's been the rest of my life uh so before, from really 13 to 25,
it was just drugs.
Drugs and alcohol.
But once you hit that 25 point
and you're now in comedy,
what is your relationship with,
what is it like with your parents at this point?
Are you still seeing both of them?
I'm still seeing both of them,
but it's the relationship that I think
anyone has with their parents around 25,
unless they're super close with them.
Like, it was fine, but it was also like they were supportive of what I did,
but they were kind of, again, it's, you know, go do it.
Oh, you want to be a comedian?
Great.
They don't know any comedians.
They're like, I don't know anyone making a living doing that.
But your mom's not in the hospital yet.
She is.
She is.
She is.
She's in the hospital.
What happened since you're how old?
22.
What happened where you finally said, okay, we now need to get help?
My grandmother and aunt had tried to get her in for a long time.
It's very hard to get somebody into a hospital against their will.
Really?
Yeah.
Even if you have doctors that say it's a person?
Yeah, because people can just sign themselves out of the hospital, and it's very dangerous for somebody who is not mentally well
to be able to sign themselves out of an institution
and go do what they want.
So they had tried that for a long time,
but it's very tough because of the laws in New York State or whatever.
I'm sure there's a good reason why it's not easy
because then we'd just be signing everybody into hospitals.
Like, go get that guy.
But whatever it is, it's very difficult.
These things aren't cheap,
but I think they had to get state aid and all that stuff.
There's no mental health care in the country.
Gary Vee is the closest thing you get to mental health.
I have a joke about it in my act.
Like, Instagram is the hustlers or the closest thing.
Mental health care is just not really paid attention to.
That's why I love this show.
People don't talk about this shit openly.
People don't talk about it at all.
And even still, like, guys, for guys, do you go to therapy?
Have you gone to therapy?
I don't, and I just did a big harangue on it on my last week of my podcast.
Because you don't like therapy?
Here's what I think about therapy.
I think you can waste a lot of time trying to get to the bottom of everything,
and I think it can be somewhat lot of time trying to get to the bottom of everything. And I think it can be
somewhat self-indulgent. And I think you kind of, like my grandfather, for example, grew up in
terribly poor circumstances. A lot of horrible things happened. You know, his brother was a
drug, you know, but my grandfather became a very successful guy. And a lot of it was because he
was, it was will and it was, you know, drive and it was putting his faith in things greater than himself.
It was very traditional religion for him, but that doesn't have to be.
I think therapy can be very good for a lot of people, but I also think it can be this
weird indulgence where people don't move forward because they think, I just have to keep digging
and plumbing the depths of all of these things instead of just moving on, accepting people
for who they are, accept people for being
imperfect, accept life as a cosmic joke to an extent, accept these things that kind of move on.
And I think it can be very good for a lot of people, but a lot of times it's just
self-indulgent horseshit that a lot of people kind of, you know, it's like we do this thing,
self-care, which is hilarious to me. People are like, it's self-care.
And it's like, imagine visiting this country and looking around and going,
well, I think the problems in America are because people are doing too much for each other.
I wish it was more of a selfish country.
Imagine that.
I wish they were doing more for themselves.
And then self-care is never like becoming a better person.
It's always like masturbating with a candle or something.
It's just stupid.
Like just I want to take more baths.
And it's like, guys, it's not about that.
We got to get away from me and self-care and it's all about me.
I think the greatest thing in the world is to realize that there's other people
and try to like listen to them and help them or whatever.
You're not wrong.
And I don't disagree with that right so but if you don't have your shit together if you haven't
figured yourself out you can't fucking help anybody else agree with me and co-sign this
statement i like that you're asking me to agree with me and co-sign this statement 100 most
therapists are very stupid people i would have you ever met if that Have you ever met one person
that said they were getting a degree in psychology
that you thought had anything to offer?
Let's be very honest about it.
It's right up there with art history
where you go, none of you.
It's never a guy.
I would rather listen to a fucking old detective
or I would rather talk to one of those people for an hour than somebody who couldn't hack it in anything and said, I'll be a shrink.
Well, listen, I don't disagree with that either.
Shout out to Drew.
Kidding.
Love Drew.
There are some shitty therapists.
Yes.
There are some shitty regular doctors.
There are some shitty everybody's.
Right.
And therapy can be like dating in the in the sense that you
have to find that right person for you and then the right there all that but you know
i it's even still but do you i guess i'm asking you specifically because there's still a stigma
and i hear it all the time that that guys still don go. A lot of men don't go. Do you
stand by what you say because of the way you feel or is part of it also because you're a man
and your ego doesn't allow you to go in there? I'm sure there is some of that, but I also think
that I'm lucky enough to do something I like with my life. I'm lucky enough to have outlets
to express myself. I'm lucky enough to get something I like with my life. I'm lucky enough to have outlets to express myself.
I'm lucky enough to get to do something that's challenging and interesting.
That doesn't mean that it's medicine and that doesn't mean that comedy is fixing me in any
way, but I do feel like, I feel like I'm able to kind of, you know, express myself and have
outlets that other people don't have.
And I'm grateful for that.
I'm against the idea of, of potentially going to therapy at a certain point i just i just don't know i i i
you know i don't know i think that like you can evolve as a person on on your own
and you could do a lot of it on your own you can but, but I also want to say this. Therapy doesn't have to be in some office building or sitting there. My friends, everything that happened to me when I
was a kid, I'm 16. I have no parents. My friend's mom became my mom. She would sit down with me at
night. Everybody else would be out drinking, whatever. There'd be nights I'd sit with her,
and we would debate whatever was going on in the news or
anything at the time. Just talk life
and what it was really like.
And that shit saved me.
It was never this therapist I
would go talk to.
Like you said, I could sit and listen to...
This show is therapeutic.
The closest thing I had to that, I had a woman named Lisa
Hoey, who's one of my best friend's mothers,
who told me I should do stand-up because that's funny. We used to drink martinis together. Long Island woman, very Hoey, who's one of my best friend's mothers, who told me I should do stand up because I was funny.
We used to drink martinis together. Long Island woman. Very funny.
I used to drink martinis and she go, nobody makes me laugh. You make me laugh. Do stand up comedy.
And you were therapeutic for her. That was therapeutic. That's what I'm saying.
And then I came back one day and I was really frustrated and I was like, it's very hard.
It sucks. I'm not making any money. And she goes, it's what you're meant to do.
Who cares if you're enjoying it?
It was such a great thing.
She goes, sometimes what we're meant to do is not what we enjoy.
And she goes, you just got to get back out there and keep doing it.
It's what you're meant to do.
She goes, I see this for you.
You know what I mean?
Wow.
How old were you then?
Then she told me that she had been on Earth for 2,000 years.
She was part of a cult with Shirley MacLaine.
It doesn't matter.
She said
Shirley MacLaine was her spiritual
the point is this
the point is this. She was
right. I am funny
and it was therapeutic and I'm I've
just had some shitty therapist. You know,
I've had and I get that there are
some old
guy who draw a picture of a tree.
I'm like, will you shut up?
Right.
Yeah.
So I am for it, but I also am wary of it only because there's a lot of hucksterism.
And I've spoken to psychologists.
It is a business as well, for sure.
A lot of people don't know what they're doing.
Yeah.
A lot of people in this profession don't know what they're doing.
And he goes, you know. So I don't know. I think there's a benefit to it,
but I also think maybe you're just better talking to someone who's stocking shelves at a grocery
store at that too. You know, while they're stocking shelves to start unloading on them.
That too. Yeah. Just right there in the aisle. Yeah. Um, I've been doing a new thing at the end
of the show and I probably should have gave you a heads up, but I don't think you'll have any problem with this.
If you could go back to your 16-year-old self
and give 16-year-old Tim Dillon advice,
and it doesn't have to be advice for when you're 16.
It could be buy stock in Apple when you're 35, whatever.
What would you tell your 16-year-old self
with the benefit of hindsight that you have now.
Start a YouTube channel earlier,
start a podcast earlier.
Social media is going to dominate.
Um,
be more attractive,
have more money,
be,
be better.
Your friends are all losers and your family sucks.
Ditch them now.
Don't waste time.
Get thin.
Be thin.
Don't.
Eating isn't that good.
Like, even though you think it is
and you're going to learn
that it's the only thing you have left soon.
Abandon it.
You know?
Get out of, get out of, get out of.
You know?
No, really? Here's the answer to that question
here's truly the answer to that fucking question nothing not one thing because you you get to where
you're going that's what and that is what you would say just keep doing what you're doing to
where you're going let it happen because there's there, like, I don't, it's one of those questions where you're like,
what would my 16-year-old self even think if I came back to them now?
They'd be like, what?
You know?
They'd be like, who's this fat pedophile?
Get away from him.
What kind of advice are you giving me?
I should start at, what?
I'm going to come back in a frazzled state
and be like,
there's something called TikTok.
It's like,
what are you going to say?
I would just,
you get where you're going.
I know brilliant people
in this business
that are doing arenas
and they were always meant
to do arenas
and I know people
in this business
that are doing comedy clubs
and selling them out
and they were meant to do that
and I know people
in this business
that wrote a play
and have a great play that no one cares about but it made them happy and they were meant to do that. And I know people in this business that wrote a play and have a great play that no one cares about, but it made them happy. And they're
meant to do that. I just, I don't know what I'm meant to do, but I know that you really don't
feel like, you know what you're meant to do. I know that I'm meant to be funny and I know that
I'll keep doing that for the rest of my life. But I, it, you know, I didn't know that I was
meant to be sitting here in LA doing podcasts. I didn't know what that was five years ago.
Right. So whatever the hell I ended up doing, I think it's kind of that AA shit, even though I'm
not like super like a program guy all the time, but like I kind of like get out of your
own way.
Like kind of like.
Yeah.
It's like.
That's great advice.
Yeah.
I don't know.
Get the fuck out of your own way.
It's great advice.
Here's the way.
This is an AA thing.
I've been in my way a lot.
This is an AA thing and it's going to sound ridiculous and it's going to sound people are going to not understand it.
It's like my life is none of my business in a way.
I do the things that I think are right, principled and whatever,
and I work as hard as I can.
What happens, I don't control.
I cannot try to manage and control every part of my life because that's when
the resentments build up because things aren't exactly the way I want them to be. And that's
when I'll start going, well, how do I fix this? How do I fix these resentments? And it's going
to be with drinking and alcohol. But if you just, if you just say to yourself, I don't know where
the hell this is going to go. Um, and you just hold onto that and you also hold on to that, and you also hold on to your integrity
to whatever degree you can,
I think you'll probably be okay.
You are, brother.
Thank you for coming on and doing this.
Thank you.
Thank you for being fucking great.
I appreciate it.
Thank you so much.
You're fantastic.
You're the best.
I love you, too.
Thanks for having me, man.
Anytime.
Yes, you're always welcome here.
Will you please plug, promote everything one more time?
The Tim Dillon Show, which is my podcast,
if you want to hear more about how therapy has really helped me,
and it is good.
The Tim Dillon Show on Apple Podcasts, YouTube, Spotify,
Tim Dillon Show YouTube channel,
Tim J. Dillon, D-I-L-L-O-N on Instagram and Twitter.
We put out some really funny videos and content.
And, you know, if this was fun for you,
then those are cool things to check out.
Yeah, definitely go check that out.
Thank you again.
Thank you.
Come back whenever you want.
I appreciate it, brother.
I am Ryan Sickler on all social media,
ryansickler.com.
We'll talk to you all next week. Take care.