Original subtitles

This one's sore.

Just at the top.

Most of the top. The heel feels good now.

Um, did you get up early and take baby back to her house?

Yeah, we went...

Had to get the kids up and had breakfast

and took Nash to school.

Came back and hung out with Danny until he went to his little dance class.

- 6:00 a.m. - What are you, a great dad or something?

Yeah, man. I put myself second.

Look into it.

- Hmm. - What are you eating already?

Smart

Less

♪ Smart ♪

♪ Less ♪

- Hi. - Hey.

- How are you doing? - Hey.

- Hi. - Hi. Good morning.

- Did you have a civilian job of any sort? - Many.

He was a fucking baggage handler.

I was a baggage handler.

- You were? - Yeah.

Also, I planted trees.

I love that. That's pretty cool.

Seven cents a tree. Not a joke.

We camped. You'd have these, like, bags with seedlings.

Packed with hundreds of them, and you go out,

and you just go, "Six feet."

Dig a hole.

Six feet.

We were like, "Oh, I need to plant 3,000 today in order to make any money."

- You wouldn't do 3,000... - Yeah, of course.

- In one day? - Of course. Every day.

- Wow. - And then, I also replaced water main

and sewage pipe in Winnipeg, Manitoba.

Huh?

- Wow, that sounds smelly. - Yeah.

I did that for, like, four or five months.

- It's like, all hard labor jobs. - Yeah.

Was this type of work

a deliberate thing from your parents?

No, they were all jobs where if you just did 'em

and you didn't do anything else for a couple of months,

you could save up a lot of money.

- No, but-- - I couldn't make that kinda money going to waiting tables.

Right. I guess, my bigger question is,

- you grew up-- -"Was it punishment?"

No, no. But you grew up in...

I don't want to call you privileged,

- but you certainly were. - I was.

But you doing working class work

in a privileged house

is different than certainly the American culture.

So, is that just Canadian culture?

- Was it deliberate on your parents part? - No.

I think it's Canadian culture. It's not unusual for...

for university students to go tree planting.

There's a sense of, like, giving back and the sense of obligation,

again, to create something bigger than yourself.

And I will say, working those jobs, as much as they sucked,

did give me a real understanding of, like,

A, I don't want to do this forever.

So, I better get my shit together.

And B, the perspective it gives you

when you fucking get...

I'm like, "Everything else is easy." Like...

- Yeah. - When people complain you're like,

-"Shut the fuck up." - Right.

I did not have a civilian job...

No, I started at ten

- doing Little House. - Wow. Isn't that wow?

Yeah. I can't imagine growing up on sets and going to school

- and so, it's just bizarre. - Yeah.

If you could wiggle your nose

and have your career be exactly where you want it to be,

where would that be?

This seems like such a road answer, but it's true.

I just want to do stuff that's fun.

And I want to be able to have more time with my family.

So, acting more than producing or vice versa?

I think a balance. I like to do a little bit of everything.

You're just staying employed, staying active.

- No big goal you're looking to attain. - No.

My goal is to be happy. That's it.

That and having longevity and staying employed

is an enormous accomplishment.

After Arrested Development, I did a bunch of stuff

that didn't pan out the way I wanted to

and I was disappointed.

It took a moment.

But I totally re-jiggered what success means to me.

And when I stopped

tying my self worth to what I do for a living,

changed everything.

I've been thinking about that on this trip.

'Cause I've been watching what you're doing as a father

even when you're out of town.

I'm like, I can squeeze in being a better dad

and be less selfish.

And just watching the way that you're doing it,

I'm... I'm really envious.

Look, I'm really lucky to have--

I got so shocked that any time you had, you were out the door with what...

- It's amazing. - Yeah.

- 'Cause I know how precious it is. - Yeah.

And then, it's gone. I'm lucky in that my parents were...

and are awesome.

And I can hear my parents' voices

saying, "This is what you need to do.

Go and do this."

"I wanna do this." "Too bad."

So many times growing up, "Well, I'd like to..."

"Too bad. It's not just you.

There are bunch of other people in this family.

It's about a group.

And you gotta do what's good for the group."

And that was fucking always

drilled into me.

I had such a different upbringing.

I mean, you know, my parents were great.

But was very, very,

very... everybody was sort of given independent responsibility.

- Mmm. - Plus, my mom was a flight attendant.

- Gone two weeks of every month. - Right.

We used to have this thing, it's kind of a joke in our family,

but it was an actual rule.

Which was, Sunday night,

- nobody in, nobody out. - That's cool.

So, it meant, no friends over for dinner and you can't go anywhere.

Sunday night was family, it was home.

I'm only using this comparison because of the business we're in,

but, you know, for as long as people have been making content,

we've been trying to figure out what makes something funny,

what doesn't make something funny

And at some point, you just kinda have to give up

and just do what you believe.

And I think I'm making a comparison to parenting,

which is like,

for as long as we live, we try to figure out,

"Maybe this works. Or maybe I need to do less of this or more of this.

- Right. - People... You can drive yourself crazy

trying to analyze.

So, you kinda just have to be like, "This is how I parent?"

What was the dynamic in your house?

- All jokes aside-- - My father was really nurturing.

He really raised me.

No. But how old were you when your dad left?

Five years old. My mom raised five of us by herself.

Right. So, what was that dynamic

at home for dinner time?

It was absolutely chaos all the time.

- It was whenever you can grab. - Was it sit-down dinner? No?

It was a lot of TV dinners and microwave.

But it was kind of a grab bag and you just... everybody for themselves.

- Was your mom home when you got home from school? - No.

- She was working one of two jobs. - Yeah.

She opened a food bank and she sometimes would

bring some of that food home for us.

- She would? - Yeah.

But a lot of the times--

- Because she was struggling to make ends meet. - Yeah, for sure.

But in high school, I remember,

I almost never ate breakfast or lunch.

Jason didn't either.

But for different reasons.

So, everybody would be eating lunch,

but I didn't have money to get lunch.

So, I would just be like, ho-hum, ho-hum.

And then, some people would be like, "You wanna have...

You wanna come over here?" I was like, "Sure."

I felt so, you know...

so embarrassed and like...

you know, so gross.

After you got successful,

did your father try to come back into your life?

Yeah. Yeah, he's a bus driver.

- Where? - For children.

So, he's happy

to spend time with kids, not just his own.

When was the last time you spoke to him?

Probably 2001 or 2002 or something like that.

I said to my sister, Tracy, I'm like,

"Let's go see dad."

She goes, "Why?" I go, "'Cause I wanna know...

I don't know any... I don't know him. I don't know anything.

So, we went to this bar, of course 'cause he was an alcoholic.

And you could tell he's really nervous.

Right away I said, "Why did you leave?"

- Really? - Yeah. And he goes--

"'Cause of questions like that."

"Check please."

I said, "Why did you leave?" My sister kicked me under the table.

And I go... "Well, I didn't come to

ask him to play catch." You know?

And so, his backstory which I found out later was...

He was raised by a massive alcoholic

who actually did die, literally,

in the gutter on the street

from alcoholism.

And then, his mom broke both her hips.

Had to put him and his sister in an orphanage,

'cause nobody was there to raise him.

And then, he went into the army right away.

He never got a chance to be a young person.

Like, screw around, go drink, party, have fun.

So, of course he did it after he got married and had five kids.

So, it was like, what? My dad has since stopped

reaching out since we started the podcast.

Because you think he's heard

- you talking about... Oh, really? - Probably.

Do you care?

I feel badly about always talking about him.

But at the same time,

you could make an effort and say...

"Holy shit. Boy, did I screw up.

I am so sorry."

But I don't think he has the wherewithal to do that.

I've always taken your lightness about it,

your freedom to talk about it,

the way that you're good natured about it as...

not that you're laughing at him

or angry at him,

it's a declaration of all the work you've done yourself

to be good with it

- and recognize the absurdity of it all. - That's exactly right.

That's exactly right.

And as my grandfather, Bill Palk, used to say,

- if you didn't laugh, you cry. - Absolutely.

And he had such the same sort of approach that you do, which like...

- "What are you gonna do?" -"What are you gonna do?"

- You gotta keep looking forward. - Yeah.

Well, Sean, I have to say,

you remind me and make me feel like it's okay

to be the part of me that I'm most proud of.

Ah, I love that.

What a beautiful thing to say.

It's such an incredible, unbelievable feeling of acceptance.

Because if you're a gay man,

you spend your life made to feel like you need to apologize for who you are.

And kind of taking care of other people's feelings

about the awkwardness they may feel about you.

So, you constantly have to take that one step and go,

"No, no, no. I don't want to have sex with you.

It's okay. You can't catch it."

You're constantly like, caretaking, caretaking.

And then, you reach a point where you're just like, "I can't do it anymore."

Let me just say this, if you weren't gay, you'd be so boring to me.

No, I think you're right. I can't imagine what that

would be like to have that as a thing that's always there gnawing at you.

Every day.

- Yeah. - Yeah.

"Can I say this, can I do this, can I have that?"

And then you go, "Ah, I'm just gonna be myself."

Can I ask you this? How old were you

when you came out to your family or your mom?"

18.

I remember my oldest brother

was in the next room when I was in the living room or the family room

and through the kitchen through the wall, he just goes.

"I know you're gay. It's cool."

- And I was like, "Awesome." - No way.

- Wow. - Yeah.

When did you actually first cognizantly go, "Oh, I'm gay."

Like, 11.

What was the moment?

- Probably the Hogan Family or... - Oh, my God!

It's so ripe for so many jokes...

We're having such a real conversation

- and I have so many jokes. - Thousand.

- Just thousands of jokes that I wanna say. - Please.

What I could have said,

"When did you know? Blowing that dude?"

- That was an easy one. - Right, that's the easy one.

No, it was when I had two in my mouth.

Two really sealed the deal.

I love you so much. It must have been such a huge part of your--

Yeah, I think it was scary.

I remember my mom wrote me,

on legal size paper,

both sides, some 15-page letter about,

you know, "You're going to hell.

I can't believe you're doing this.

- Really? - The family. And then, I'm like...

I said to her face and go, "Great. I don't have a dad or a mom now."

And then, that's when I kinda felt, and I was 18.

And I was like, "Well, I guess, I'm on my own."

The survival thing kicks into further gear

because even before that you're in survival gear

just 'cause of the way we were raised.

So, I've never ever, ever stopped being in survival mode.

That's why I'm cleaning, I'm doing...

I gotta make sure of everything.

You know what I mean? It's like, or else I don't know what will happen.

Because nobody else has got it

- for you. - Yes. That's exactly right.

- So, you gotta get it. - That's exactly right.

That's exactly right.

If I don't do it--

- I have felt like that since I was ten. - Really?

Well, yeah.

I definitely could have done without

the massive anxiety

I had every time there was a big grading period in school.

Because if you don't have a work permit, you can't work.

And that work permit needs to get renewed every six months.

- Based on? - Based on your grades at school.

- Oh, really? - Yeah.

And being on a television series

year after year after year after year,

if your work permit gets revoked,

you have to get written off the show

and if you are the lead on the show,

the show falls apart.

- A lot of pressure. - So, not only would we not have any money at the house.

All those people are out of work.

So, studying for mid-terms and finals,

starting in seventh grade and all the way through 12th...

You felt that stress and pressure.

- Massive, crippling stress. - Wow, dude!

But wait. That's what I'm asking--

I never even thought about that.

- That's insane. - You don't have like,

any kind of resentment about the fact that

you had to carry that stress and pressure.

No. Because my parents were trying as hard as they could.

- Were they strict? - Oh, yeah.

Very, very strict.

- About? - About like, curfew and--

So funny. I had this idea of you being, 17

- and marauding around Los Angeles. - Yeah.

Fucking doing rails on Coldwater Canyon.

- Yeah. - I've always been a people pleaser.

I've never been a, "Oh, fuck 'em,"

you know, I gotta make myself happy and that's it.

Although, I am pretty good about, you know,

taking care of number one.

I think the thing that kept me from imploding

was the healthy level of concern about

what people would think of me.

You know, first and foremost, my parents.

Do you feel like because

you did as a kid and as a teen and as a young man,

work so much in TV

- and you felt that people didn't respect what you did. - Yes.

Certainly you... Yeah.

I'm not chasing that. I don't have some self-loathing about, you know,

what I did was not respectable.

Then, now it is.

I'm not distracted by that.

But I do really try to every day

continue to do things

that allow me to feel proud of myself.

I love that. That's great.

So, Sean, what about you? Where do you see yourself?

- What do you wanna do? - Hey, man.

Thanks. Oh, boy.

If you can't be real,

I hate the way you joke around all the time.

- Welcome home, Sean. - Thank you.

This is exciting. Chicago.

So, about a mile that way

was a dinner theater

and my mom had tickets to Fiddler On The Roof.

She didn't wanna not use them,

so the day I was born, she left the hospital

to go see Fiddler On The Roof in that theater.

Left me in the hospital.

No way.

Yeah. So, she just cinched up the diaper and went.

I was the fifth one. That was probably why she like...

"You guys got this? Great."

You can't ask for better care.

No, my mom is the best mom ever.

The end of the story on the plane about the letter that she wrote about

when after I came out.

I didn't really finish it, but, you know,

she did a 180 in like...

You know, it was like, I was her favorite then.

- Yes. - Once she became educated. You know?

How long did it take her?

Couple of years.

Yeah, this is nuts.

This is crazy. Settled.

And then, this is the kitchen.

Is this you here, Will?

That's me.

Wow. Crazy.

- Wow! - That's the kitchen.

Wait, how do you get to JB's room?

Around this way. Come follow me. Thanks.

- So, that's your-- - It's almost like you've never been in the Peninsula suite.

So, this is where I'll be staying.

I'll be sleeping, I have a big decision to make

whether I'm gonna be on this bed or that bed?

- Maybe I'll switch throughout the night. - Okay.

So, this is JB's room.

So, we go this way.

By the way, guys... Oh, well, it's done.

So, thank you for the nice room.

No, this is your town.

- No, I know. - I wish you were getting two nights here.

- I know, really. It's only for one night. - I know.

- And this is yours. - Yeah.

- And there's a little kitchen. - Wait, where's the little kitchen?

- We missed it. - Oh, we missed it.

It's right there.

This takes me usually like,

three and half, 3:40 to clean.

- Hey, Jay. - Hi.

You got your Skinny Pop and think! bars in here.

Jay, wait till you see the think! bars in here.

You're gonna be doing so much thinking on the can.

- Where are they? - Yeah.

Your Skinny Pop.

Skinny Pop and think! bars.

Nothing builds a plug like a think! bar and a Skinny Pop.

- Oh, my God! - Oh, my Jesus!

Mazel tov.

What if Sean's cards, all they said was,

"Hi, I'm Sean. Hi, I'm Sean."

- "Hi, I'm Sean." - Card after card.

Card after card. "Hi, I'm Sean."

15 minutes to showtime.

- Hmm? - 15 minutes.

You need to throw up?

No, I don't...

Uh...

What you got, Todd?

Welcome to Portillo's.

We can't mow this down right now. Right?

Hi.

Howdy.

- Chocolate shake. A shake beer. - Root beer.

- All diet cokes. - Chocolate cake shake there.

- Yup. - Chocolate cake here instead of fries.

He's obsessed with the cake shake, Jason.

Who got the root beer?

Have we got a seven-year-old on the crew?

Look what I'm doing.

You think this is a good idea?

My kingdom for a paper towel. Am I right?

I'm guessing you need a spoon for these.

Oh, here.

Beef with cheese, I think it's

- Michonne, is it not? Did you want cheese on yours? - No.

There's root beer. We got root beer.

- You? - Yeah.

It's been a lot of buildup. Here we go.

This is where I judge you.

I'm supposed to put the cheese sauce on it?

I've never done that.

Uh, that's what Will did.

Seany, you happy?

I'm the happiest.

- Are you? - Mmm-hmm.

- This is your happy space. Right? - Oh, my God.

You're in Chicago.

You're having Portillo's.

The Sox won, the Cubs won, the Bears won.

- That will change your life. - Yeah.

I keep wanting to put this down, but it's good.

Thank you for being here. It means the world to us.

I will be burping Portillo's throughout the night.

Do you want me to throw up

some of my Gasex in your mouth?

No, no. Gross. Gross. And by the way,

Sean thought it would be a good idea for all of us to have

like, these beef sandwiches and...

- and chocolate-- - Chocolate cake shake.

Chocolate cake shake.

Before the show,

and Jason who hasn't had anything but a salad for the last, you know,

four and a half years,

it's tough on your system.

I might need a stitch later.

I wanna share a couple of stories

from my childhood, since I grew up here.

Forgive me if you've heard this,

but I can't remember how much of my mom's eye I told you about.

Yeah!

No, bless it.

At two-years-old, my mom had cancer,

so she had one of her eyes taken out.

Then, she had the five kids, my dad left.

You know that story... when I was five

and then, my mom raised all five of us.

No, they remember all these hilarious stories.

He didn't really leave, he put it in drive and punched it.

- Yeah. - It was a tire screech.

Okay, so...

I love how much joy you get out of your own pain.

- If you don't laugh, you cry. - Yeah.

So, when I became a tiny bit successful,

I was like, "Mom, I wanna buy the house that we grew up in

and the one next to it.

And on the other side, knock all three down

and build your house and that's what I did.

Which was fantastic.

She deserved it.

Tore our entire family apart. But anyway...

She comes in the door

and she cries her eye out.

She's touching everything. She's like,

"Oh, my God. Nobody has done anything like this for me in my entire life.

I don't know if I would have picked out that couch."

And that's my mom.

Yeah!

My sister brought a gift for you guys today.

- Oh, my God! - Please let it be the eye.

- No! - Oh, my God!

You can't see this, but it's an eye.

That's my mom's eye.

- Is this really your mom's eye? - Yes!

I brought it back to Chicago.

Oh!

- Oh! - I'm curious.

It has no odor whatsoever.

- It's a glass eye. - It's a very pretty eye.

She looks like, when she got fitted for this, she may have been a little stoned.

Or finished a long lap in a pool.

Well, not my Mom. Nope.

Anyway, for my guest tonight,

I wanted to get someone who has some Chicago roots.

He was in the original cast of The Real Live Brady Bunch back in the '90s

which was one of the funniest things ever I ever saw.

He's since appeared in parts alongside Will Ferrell in Elf, Talladega Nights.

- And even appeared one of my all-time favorite TV shows - Oh, my God!

- that has its name in the title. - It's Andy.

Now, he may not have had his own talk show

with his own name in the title. Yet...

- But he's the biggest reason... - Richter?

- Conan O'Brien did. - Richter.

It's Andy Richter!

Andy!

Hi.

How nice of you to come out here and join.

Speaking of jewelry, have you seen Sean's new jewelry line?

- Oh, wow! - Yeah, it's nice. Right?

- Dandy. - Yeah. Wait, wait, wait.

Do you ever jerk-off in front of this?

Answer him.

I mean, it's a natural... We were were all thinking it.

- So gross. - Wait. When was the last time you were here?

Thanksgiving.

Nothing says winter cozy holiday

than Chicago.

- Right. - And the suburbs of it.

I just... fantasized about that.

'Cause you know, it's like, 79 on Christmas in LA.

It's like, you wanna blow your brains out.

- Yeah. - I know.

It's 79--

These unbelievable coastal elites. Right?

I mean...

You didn't grow up... I mean, you weren't born here--

No. I grew up in Yorkville.

- Okay. - Yorkville!

Yeah!

I got the fun thing of after being out of the house for two years,

got to move back home.

- Uh-oh. - Oh, man!

What was the first big problem?

Was it bringing a girl home?

- Was it your-- - That wasn't that big of a problem.

Dude!

- It should be. - Dude!

Did they find your bong?

No, no. It's just my family...

And they're here, they'll attest.

They're really annoying.

One asshole after another.

You're maybe one of the quickest people ever of all time.

But that's like 'cause of improv. Improv Olympics.

I was in Improv Olympics which is Del Close

you know, school of improv.

- Yeah, yeah. - Yeah, there we go.

What event did you excel in?

Being fucking funny.

Yeah.

So, how did you and Conan meet and how did that happen?

Ah... We arranged lunch in Los Angeles

at Junior's Delicatessen.

Was it just to be friends or was there?

No, this was to get a job as a writer on the show.

Oh, you think it was a date?

Well, I don't know. I mean,

- they're both handsome as always. - Obviously.

- You know? - We were spooning in a booth.

You guys did so many unbelievable sketches.

Every day, were you like, "Fuck yeah. I'm so psyched to go in there

and do these bits and work on this show."

- No. - Great. Good Night.

No. I mean, you know...

How long was the day for you?

10:00 a.m. and usually leave around midnight.

The fuck would you do for 14 hours.

It's a one-hour show.

Well, when I got hired, I was a writer.

You know, I was on the show, too, in the beginning.

Look at how tired he is thinking about it.

Ah.

They portaled the portal.

- No, no, no. - Cool it

Who fed you your soup?

Wait, wait. Should I just tell you something which is really on brand for this.

And I just want to talk about what happened backstage today.

So, everywhere we go, we have the special water

and almonds and popcorn.

And Jay...

I didn't ask for any of it.

So, Jason starts going...

It dawns on him and I'm like, "Everywhere we go,

- with the popcorn and the almonds - Yeah.

- and lemon water. - Skinny Pop.

And they're like, "Where is this coming from?"

And we find out...

Well, that... Look.

I... Hey.

We're all staying in the same hotel room.

We thought it'd be fun and funny. It's a fucking drag.

Are you really?

- Are you really staying? - Yeah, yeah, yeah.

- No, it's nice. It's fun, it's great. - Oh, my God!

- Oh, my God! - Whomever was tasked with getting the stuff

in the hotel room,

in the dressing room...

must think I'm a fucking monster.

Yeah.

- But, but... - And rightfully so.

But the point is...

how come you and Sean don't have anything. And I was able to...

You know, when you get on the high road...

And you're able to be just super-chill on the high road and you go...

"'Cause we don't need anything."

- I know, I know, I know. - Aw.

Aw!

- It's gonna be all right? - I know, I know.

Getting back to Chicago

and everybody knows there's so many great music

and great bands, everything like that are from here.

Did you have anything like that growing up?

Were you... Just anybody you loved,

or maybe somebody now or whatever?

Like, at the time when I was young here, like,

- Smashing Pumpkins were still like around. You know? - Yeah!

And then there was Wilco.

Wilco is amazing.

Well, it's so funny because I was reading about Jeff Tweedy

and how amazing he is.

And he's not only like,

a songwriter and a musician

and a record producer and Grammy winner.

He's also here!

- What? - Jeff Tweedy!

No!

Oh, my gosh.

This guy's freaking out right now.

- What? - Have you never met him?

I have met him.

I met you on a tour bus, but I was not in a real good place to talk

'cause I was a little starstruck, like I am now.

- Oh, no. - Good Lord!

I was asked to come on the show and I was like, "Oh, that's exciting."

- And I dreamt that you were my best friend. - Yeah.

- A lot of people have had that dream. - And so...

I have that dream every night.

So, in my dream, I get so excited about getting to do this...

- Yeah. - that I go and tell you...

Sure.

And you start crying.

- Because I ruined the surprise of me being here for you. - Right.

Because I forgot that you were on the show, too.

Because I was excited about meeting you.

No!

But you were really upset with me.

Well, it's very upsetting to hear it even now as a dream.

- Can I... Can I ask-- - First of all.

- Calm down. - Okay.

So...

Sean, let the robot speak.

I'm assuming when you're writing,

you're writing and then the next word kinda follows the next

and how should the story go

and it just kinda falls out in a natural progression.

Is it the same way when you're strumming

and you're kinda trying to come up with a new song

and you find a good rhythm.

And then, just naturally, because you have great taste,

"Oh, this chord would sound good after that."

And by the end of a few minutes, you got yourself a song?

That can happen. But that's not normally how it happens.

Is it normally like,

there's a certain structure, a certain chord has to follow another sharp thing...

- Is there like a recipe? - Oh. no...

- Oh, you do-- - His brain is so logical.

I love it. I love you so much.

And I'm pulling for you.

"How... how does music?"

-"How make music?" -"How does music?"

I not know things. "Processing."

- Help me, Jeff. - I can help you.

You improvise conversation all the time.

Because you have a vocabulary.

And you learn certain phrases and things that you like.

It's no different with music.

There are certain building blocks of the vocabulary

that you get from your record collection.

And from things that you like and things you care about

and other songs that you've written.

And eventually,

it does become sort of conversant.

But the most fun part about doing it

- is the discovery for yourself. - Right.

You don't really know where it's gonna go

and that's my favorite part of it.

- Would you sing us a song right now? - Wait, what?

We can't pay for that.

I didn't bring a guitar.

- And yeah, you didn't pay for that. - Wait, you didn't--

Uh-oh.

Oh, my God!

This is blowing my mind.

I can't tell you how excited we are

and Jason and Will are that you're here.

Me, too. And me, too.

I know Andy.

- Wait, do you guys know each other? - Yeah.

- Conan was our first ever performance with Uncle Tupelo. - No way.

Your stage director said,

"There's three million people watching, don't fuck it up."

Last year we would have killed for that number.

I was gonna say that I had to teach myself

how to ignore the guy yawning.

- Uh-huh. - That un-laughing mother fucker,

I stare at him every time.

I know, I know.

We can have 95 percent of our life going really, really well

and five percent doesn't... There's always gonna be five percent.

But I realize that like, "Yeah, I'm so stupid

for focusing on that, too."

Twitter is based on it.

- Ah, yeah. - Twitter is based on that.

- It's true. - Like, that reality.

All right.

am an American Aquarium drinker

I assassin down the avenue

I'm hiding out In the big city blinking

What was I thinking When I let go of you?

Let's forget about The tongue tied lightning

Let's undress just like Cross eyed strangers

That was so cool.

DId you guys really eat Portillo's right now for this show?

Wait, I still got my shake in here.

Oh, God, it's probably warm.

Is this supposed to be you guys?

- I know, Granny Hayes with the shades. - Yeah.

What a tribute.

You have any idea how delicious this is?

Let me just try a bite.

- It's so moist. - Feed it to me.

No, I don't want fucking a big frosting. I'm not like you.

I'll just take the cake. I don't need all the shit.

- You don't want frosting? - No.

Oof, you don't have to put so much lip on it.

You don't do a tooth drag?

- I'll have a little bit of fro... - Oh, yeah.

You know what...

Just a little bit of frosting from the middle section.

Oh, sorry, I didn't even know

- exactly how you were-- - The frosting between the cheeks is the way

I like it, not the one on the outside.

Yeah, I do a teeth drag, so I don't get your disease.

How was it?

Mmm.

Not great.

- Well... - It's better in a shake.

I thought it was delicious.

Hey, man, great show.

- Great show. - Yeah. Thanks, good show. You guys, too.

No, really good.

Like, tonight felt like a live talk show,

like it should be.

With this guy and the musical guest

and it just went like this

as opposed to, you know, this.

We might wanna lean into...

- two guests every show. - Yeah.

- And just have them move down the couch. - Yeah, and a writer.

- Huh? - And a writer.

Look, he's so angry about the writing.

"No, we don't fucking rehearse shit. That's what..."

Yeah, I would want a writer to write.

I'm so tired of writing intros and like, this thing.

And come here with a...

like other questions, other--

You did start with a pre-determined story tonight.

- I did because-- - And you got another one for this, too.

- Absolutely. I have a couple of them. - Good for you.

Here's a great thing, there are no rules.

We can do whatever we want.

Is there any plastic wear

because I might get into that thing?

Yeah. Well, use your...

- Hands? - Your God forks.

You know?

-"God forks." - You know?

It's weird having two shows.

To do it and you're like... And it's like,

Oh, you got another lull before another show.

- Oh, wow. - Oh, my God.

Oh, my God.

Margaret, I can't.

Having an anxiety attack.

Where'd you go, JB?

I'm coming. I'm just freshening my lips.

Wait, wait, wait, wait, wait.

I think we have to sign this wall at some point. Don't we?

Nobody's gonna see it.

No.

You guys ready?

- Oh, my God! - Yeah.

Trying to wake up.

I know. Me, too.

Okay.

- Okay. - Oh, fuck.

- Just have to get excited about it. - Holy fuck!

Oh, jeez.

Here we go. I'm already up, so I don't need to be hit.

- I'm up, too. - Okay.

I'm up, too. We gotta make...

We gotta make some kind of announcement.

- We're gonna say-- - So, like, they can't use cellphones.

Right, you can't use cellphones.

We're sorry that we're running late.

You do need to wake up just a little bit though. Right?

- Oh, fuck. - Stop it!

Stop, stop it. Stop, stop it.

Okay. So...

Somebody do it like in an accent.

Okay, so in an accent?

Yeah, an accent, so they don't think it's you.

- So-- - Any accent.

Welcome to Chicago. Something like that?

- Yeah. And what else you can-- - And then...

No flash photography.

- Right. And what else? - And put your fucking cellphones away.

- Yeah. - I think I can hear an echo.

- Like, we might already be on. - Yeah. It's...

- Hold on. Mic's on? - Well then...

we know what we have to say.

- Welcome... - To SmartLess!

Run, run, run, run!

Hello, Chicago!

Wow!

For those of you who might not know,

I'm actually from here.

And when I was a kid,

my dad's mom, my grandma on that side...

So, it's already a good story.

- Jesus. - Aw!

We're already off to a booming start.

So, she used to crochet all these animals.

Like, there was a dinosaur and a duck

and like a mouse and a dog.

And so, she gave us these things.

And I used to cut out the hole, the dinosaur's face...

mouth and I used to fuck it.

Wait...

- You know, there's a few thousand people out here. - Wait, wait.

Okay, so, wait.

- So, wait. - Oh, good, there's more.

Wait. Did it matter what kind of dinosaur?

Like, would you not get turned on

- by a Tyrannosaurus Rex, - No!

- but definitely a Brontosaurus? - Great question.

No, there's one dinosaur

and the mouth is stuck open like that.

I looked at it like, "Oh, I'll just cut a hole in it."

Wait a second, wait a second.

Just because we're back in your hometown,

- you gotta tell the story... - It's a safe space.

Oh, 'cause everybody doesn't masturbate, Will.

Not into the mouths of a crotcheted dinosaur.

- Just into loose socks. - I'm sorry.

Nothing.

Um...

Tonight, on a very special SmartLess...

What the hell?

- All right. So, we're gonna get to the guest. - Wow!

So, this guy is amazing.

One of his quotes is... I love this quote.

"It doesn't matter how many times you fail,

you only have to be right once

and everybody says you're an overnight success.

- Woah! - He went from banking

to bartending to business software.

He's one of the pioneers of putting audio on the internet.

He not only buys and sells companies,

he's also immersed in the entertainment business

as the co-owner of 2929 Entertainment.

He's not one of my favorite sharks,

he is my favorite shark!

- It's Mark Cuban! - Mark Cuban!

What!

Oh, let's go, let's go.

- Oh! - Wow!

Good to have you on here.

- Thank you. - Nice.

- Shit! Hey, man! - Hey!

Thanks for having me out here.

- Hey. - Sean.

Oh, yeah. Absolutely.

Where do you want me? Right there?

- Oh, look at this. - Yes.

- How nice of you. - With the shoes.

With the shoes.

Let's start with the shoes.

- Now, are you a sneaker head? - I'm not. I'm not, really.

Tell us about them.

There is a guy who plays on our team,

named Luka Doncic.

- Sure. Sure. - Yeah.

And these are his shoes.

Oh, I got it.

Every now and then, I pull 'em out.

- Right. - Like you should.

- Like I should. - Yeah.

- Yeah. - Yo, you gotta make the big guy happy.

And they're great and they match.

Look at you, that's great.

- I mean... - Sharp suit.

We were gonna fly you out, like, real nice...

You know, 'cause you were so nice to come out. He was like,

-"I fly myself." - God, that's good living.

I am the luckiest mother fucker in the entire world.

Do you... You probably do. Tell us if you do.

You remember the moment that you were first a billionaire?

- Fuck yeah, I remember. - Yeah, so.

We had this big IPO.

And the stock just kept on going up.

And I knew exactly what the price had to be

- in order for me to become a billionaire. - Right.

And so, you know, in the old PCs,

you can hit F5 to refresh your Yahoo Finance.

F5. Boom, boom, boom. Kinda like Sean in his story.

Boom, boom, boom, boom.

And then, it was like,

right when the market opens,

so I'm just sitting there, basically, mostly naked

- and I did a-- - At home?

- At home. Right. - By yourself?

- By myself. - Hitting that F5.

Yeah.

You were just by yourself at home

in your fucking home computer going,

"Am I a billionaire?"

Yes. And then, I did my little billionaire dance.

Right? I was just like, "Hey!"

- That's crazy. - What did you do, buy something?

No. Because I knew, you know,

- it might only be a second. Right? - Right, right.

Just like Sean's story.

Oh, my God. Sean.

That's good.

What did you guys, do this?

Yeah. Okay, good.

Well, I think...

I think everybody here has had the fantasy of like,

"What if I won the lottery? If I become...

What's my fantasy, big thing to buy?"

- Yeah. - What was it?

Basketball team.

How do you buy a basketball team?

You write a big motherfucking check.

That's what you do.

So, you paid how much?

$285 million.

- And now, it's worth... - I mean, I'm like...

- Three billion. - Oh, my God.

That's crazy.

Good for you.

I can't believe you own a team. Okay.

So, how do you determine what companies you wanna invest in?

Or where you wanna put your money?

You know, it really depends on what the product is.

If it's something people obviously need

and the person who creates it is smart,

then, I quickly try to invest.

Like, we started costplusdrugs.com.

Yes. I was gonna ask you about this.

This is... Have you heard about what he's doing?

- I haven't. Tell me. - It is unbelievable. It's amazing.

So, it's called costplusdrugs.com.

- Right? - Yeah.

We can sell direct to consumers

and so, there's drugs that we'll sell for six dollars

that everybody else is selling for $400.

- That's amazing. - Wow!

So, my husband, Scotty, he's got diabetes since he was 17 years old.

It's hilarious.

But...

Whenever I introduce him, I go,

"This is my husband, Scotty. He's gonna die from diabetes."

Now, will that be on your list? Insulin?

So, to do insulin,

- you gotta create something called a biosimilar. - So, it's a mess.

- It's hard. - Yeah.

And so, we're looking at starting that process.

So, you're talking to a dumbass.

- Confirmed. - Confirmed.

So, somebody comes on Shark Tank,

what they do is pitch you an idea

and you decide whether that's a great idea

and if it's a better idea than the other two people that pitched,

- they get, what? Funding for their idea? - Yeah.

- Basically, yeah. - Mark, just as an aside, I'm so sorry, man.

Never watched the show, has he?

I've... I've... I've...

Guys, I'm...

Don't... Fuck...

They're fucking booing you, dude!

Should we go to a commercial? Let's go to a commercial.

You mind if I pitch you a product right now?

- Let's go. - Okay.

- Wait, wait, wait. What you-- - Oh, you gonna go up there. Come on.

Actually, I'm gonna bring out my husband, Scotty.

So, we can do it street fashion.

Scotty is here.

Stand up, he's gonna be dead soon.

- Yeah. - Don't get too attached to him.

I know. I'm gonna die from diabetes.

- Oh, my God. - Okay.

All right. So, here we go.

Scotty!

Scotty!

- Shh. - Shut the fuck up!

Shh, shh.

- We're pitching. - Okay, ready.

Hey, sharks.

My name is Sean.

And I'm Scotty.

They're good.

And we're from...

Hollywood, California.

And we're looking for...

Two million dollars...

for two percent of our company...

Doggie Defence.

Yeah.

When you're loading the dishwasher,

does your dog come out and clean the plates before the dishwasher does?

Ours does. Which gives us...

Pause for concern.

Oh, God!

Oh, boy.

Let me tell you a little...

Tale.

We came up with a fence barrier

that goes around your dishwasher door

that deters your dog from accessing the dishes.

And with that defence up,

our dog is no longer...

Barking up the wrong tree.

So, sharks,

don't leave your dishes in a rough state.

Who wants to be the first one to join...

Our pack.

Whoo!

- Sean... - Yeah.

That was really weird.

Two million dollars.

I'm saying, right, when you pull the dishwasher down

and you're doing them.

- And the dog comes out-- - No, I got it, Sean. We get it.

- I got it. - Okay.

I just wanted to hear you once say...

- I'm out. - That's right.

- Oh! - Thank you for coming.

Thank you for making us smarter. I learned stuff.

- I can't wait to watch more of Shark Tank. I love you. - Thank you.

- Thank you for being here. - Mark Cuban! The great Mark Cuban!

- Thank you, everybody. - Mark Cuban!

That was so much fun.

So much fun.

I like the idea of you and Scotty

- rehearsing your Shark Tank pitch. - Yes.

That's what I was doing.

In the other room the other night,

when you guys were, "Where are you guys going?"

I'm like, "I'll be right back."

Where's Scotty?

- Can we just get Scotty for one more second? - Scotty, hurry back out here.

Scotty, get back out here.

Still alive.

Again, I just wanna get back to...

Sorry, not to get to the nuts and bolts of it.

So, when you guys were rehearsing your bit...

- Yeah. - Mmm-hmm.

Was Sean super-bossy?

- Yeah. Yeah. A little bit. - He was.

Yeah, little bit. Not gonna lie.

- Was he? - Yeah, a little bit.

Look, he's got his diabetes pod.

- You gotta be careful. - Yeah, I have my pod right there.

Goodbye.

- Yeah. - Not dead yet.

- Not dead yet. - No.

And so, you guys have been married for a number of years now.

- 15 years. - Whoo!

Scotty, before you guys were married,

did you know about the dinosaur story?

No.

- No. - But I've heard about it since.

- Right. - But not before we were married.

- Yeah. - Huh?

- Would that have affected your... - Decision.

No, this is a fair question.

No. No, of course. So...

Scotty, how did you used to masturbate?

All right.

A lot more carefully.

- A lot more carefully. - A lot more carefully.

And if somebody came in to catch you,

would you say, like, "Don't go away."

Ah, this is a bad one.

- Oh. - Oh, my God.

He's trying to do a bye.

I'm trying to do a bye. I'm trying to do a bye.

- Yeah. - I mean, did you ever worry

when you were inside the dinosaur's mouth

that it might somehow bite.

Oh, bye!

Thank you, Chicago!

Thank you, thank you, thank you, thank you.

Thank you.

Yo, where should we go?

Right here.

- I can't reach there though. - I can do it.

- Oh. - Oh, God.

We got you.

You're left-handed.

Wow. You really climbed up there.

Hey!

You guys, thank you for coming out.

Hi, guys. How are you?

Thank you so much for coming, you guys.

Here we go!

I'm gonna eat that in the car.

Turn around.

- You are so sweet. - I've had a lot of work done.

- So sweet. - Thank you so much.

Oh, my God. I can't believe I'm signing a Blues hat.

Oh, man. That's tough.

Okay. All right.

There you go. Hi, guys.

Did you get yourself a hoagie?

Yeah, somebody gave me a...

- Somebody gave you a sandwich. - Yeah.

Are you going to eat that?

- Yes. - You don't think

they injected anything into it, do you?

Thank you for coming, you guys.

And now, tomorrow you're feeling... You like your medicine.

Yo guys are gonna... Your heads are gonna blow off.

- You know, you're building it up pretty high. - I know.

They are famous.

- No? - Very famous.

Hey, Will.

How'd you do out there?

I just did a bunch of people, they were signing stuff.

Did you get any phone numbers?

You know...

They're all waiting there. So nice.

Bye, guys.