01x04 - Portillo's for the Burp

[bunniefuu]

This one's sore.

Just at the top.

- Most of the top.
The heel feels good now.
- [spits]

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 ♪

- [Jason] Hi.
- [air hostess] Hey.

- [Jason] How are you doing?
- [air hostess] Hey.

- [Will] Hi.
- [air hostess] Hi.
Good morning.

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

He was a f*cking
baggage handler.

I was a baggage handler.

- [Sean] 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.

[grunts] 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...
- [Will] Yeah, of course.

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

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

and sewage pipe in
Winnipeg, Manitoba.

[Jason] Huh?

- Wow, that sounds smelly.
- [Will] Yeah.

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

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

[Jason] 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?"

[Jason] 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 sh*t together.

And B, the perspective
it gives you

when you f*cking get...

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

- [Sean] Yeah.
- When people complain
you're like,

-"Shut the f*ck up."
- Right.

I did not have
a civilian job...

[chuckles]

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.
- [Will] Yeah.

[Jason] 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.
- [Will] 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.
- [Will] 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 f*cking 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.
- [Jason] Plus, my mom
was a flight attendant.

- Gone two weeks
of every month.
- [Will] 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.
- [Sean] 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--
- [Sean] My father
was really nurturing.

He really raised me.
[chuckles]

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.
- [Sean] Yeah.

She opened a food bank
and she sometimes would

bring some of that food
home for us.

- [Will] 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.

- [all chuckling]
- 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,
h*-hum, h*-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.

[Jason] After you
got successful,

did your father try
to come back into your life?

Yeah. Yeah, he's a bus driver.

- [Will] Where?
- For children.

So, he's happy

to spend time with kids,
not just his own.

[all laughing]

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?"

- [Will] Really?
- Yeah. And he goes--

"'Cause of questions
like that."

- [all chuckling]
-"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 sh*t.
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...

- [Jason] "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 g*y 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 g*y,
you'd be so boring to me.

[all chuckling]

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.

- [Will] 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?"

[Sean] 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 g*y.
It's cool."

- And I was like, "Awesome."
- [Will] No way.

- Wow.
- [Sean] Yeah.

When did you actually first
cognizantly go, "Oh, I'm g*y."

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.
- [Jason] Thousand.

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

What I could have said,

-"When did you know?
Blowing that dude?"
- [all chuckling]

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

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

[Will] 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.

- [Will] 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.

- [Will] 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?

[Jason] 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!

[Sean] 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.
- [Jason] Yeah.

f*cking doing rails
on Coldwater Canyon.

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

I've never been a,
"Oh, f*ck '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.

- [chuckles]
- [Jason] 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.
- [Jason] 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?
- [groans] Hey, man.

[groans] Thanks. Oh, boy.

If you can't be real,

I hate the way you joke around
all the time.

[laughs]

- 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.

[Will] No way.

[Jason] 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."

[Jason] You can't ask
for better care.

[Sean] 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.

- [Will] Yes.
- Once she became educated.
You know?

[Will] How long
did it take her?

Couple of years.

[Will] Yeah, this is nuts.

[whistling]

[Will] This is crazy. Settled.

And then, this is the kitchen.

[Sean] Is this you here, Will?

[Will] That's me.

Wow. Crazy.

- [Will] 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.

[Jason] 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.

- [Sean] And this is yours.
- [Will] Yeah.

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

- [Will] We missed it.
- Oh, we missed it.

It's right there.

This takes me usually like,

three and half, 3:40 to clean.

[Sean chuckles]

- Hey, Jay.
- [Jason] Hi.

[Sean] 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.

[all chuckling]

- Where are they?
- [Will] Yeah.

Your Skinny Pop.

Skinny Pop and think! bars.

- Nothing builds a plug like
a think! bar and a Skinny Pop.
- [all chuckling]

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

- [glass breaking]
- Mazel tov.

[crowd noises]

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

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

[Sean laughs]

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

[Will] Card after card.
"Hi, I'm Sean."

[Will and Sean chuckle]



- Hmm?
- 15 minutes.

You need to throw up?

No, I don't...
[imitates barfing]

Uh...

What you got, Todd?

[Todd] Welcome to Portillo's.

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

Hi.

Howdy.

- [Todd] 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?
- [Sean grunts]

My kingdom for a paper towel.
Am I right?

[slurps]

I'm guessing you need
a spoon for these.

Oh, here.

[Jason] Beef with cheese,
I think it's

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

[Will] There's root beer.
We got root beer.

- You?
- [Sean] Yeah.

[Will] 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.

- [Will] Are you?
- Mmm-hmm.

- [Will] 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.
- [Jason] Yeah.

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

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

I will be burping Portillo's
throughout the night.

[Jason] Do you want me
to throw up

- some of my Gasex
in your mouth?
- [burps]

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.

[Will] Chocolate cake shake.

[crowd cheering]

[Will] 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.

[chuckles] I might need
a stitch later.

[crowd laughing]

[Sean] I wanna share
a couple of stories

from my childhood,
since I grew up here.

[crowd clapping]

[Sean] Forgive me
if you've heard this,

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

[chuckling] Yeah!

No, bless it.

[Sean] 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.

[all laughing]

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

[all laughing]

- Yeah.
- It was a tire screech.

- [crowd laughs]
- Okay, so...

[all laughing]

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

- If you don't laugh, you cry.
- [Will] Yeah.

- [Jason chuckles]
- 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...
- [crowd laughs]

[Sean] She comes in the door

and she cries her eye out.

- [all laughing]
- [Sean] 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."

[all laughing]

And that's my mom.

- [Will] Yeah!
- [crowd cheering]

My sister brought a gift
for you guys today.

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

- No! [chuckles]
- Oh, my God!

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

[crowd gasping]

That's my mom's eye.

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

[crowd laughs]

[Sean laughs]

I brought it back to Chicago.

- [Will] Oh!
- [crowd cheering]

- [Will] Oh!
- I'm curious.

[crowd gasping]

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.

[all laughing]

Or finished a long lap
in a pool.

[Sean chuckles]

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?

- [Sean] Conan O'Brien did.
- Richter.

[Sean and Will]
It's Andy Richter!

[all cheering]

[Will] Andy!

Hi.

[Jason] How nice of you to
come out here and join.

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

[all laughing]

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

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

[Jason chuckles]

Do you ever jerk-off
in front of this?

[all laughing]

[Will] Answer him.

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

[all laughing]

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

Thanksgiving.

Nothing says winter
cozy holiday

than Chicago.

- [Will] Right.
- And the suburbs of it.

I just... fantasized
about that.

'Cause you know, it's like,


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

- Yeah.
- [Sean] I know.

It's 79--

These unbelievable
coastal elites. Right?

- I mean...
- [crowd laughs]

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

No. I grew up in Yorkville.

- Okay.
- Yorkville!

- [crowd cheering]
- Yeah!

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

got to move back home.

- [Will] Uh-oh.
- Oh, man!

- [kisses]
- [all laughing]

What was the first
big problem?

Was it bringing a girl home?

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

- [all chuckling]
- [Will] Dude!

- It should be.
- [Will] Dude!

Did they find your bong?

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

And they're here,
they'll attest.

They're really annoying.

[all laughing]

- One as*h*le after another.
- [all laughing]

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.

- [Jason] Yeah, yeah.
- Yeah, there we go.

What event did you excel in?

- Being f*cking funny.
- [crowd laughs]

- [Will laughs]
- [Andy] 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.

- [Jason] You know?
- We were spooning in a booth.

[Will] You guys did so many
unbelievable sketches.

Every day, were you like,
"f*ck 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?


leave around midnight.

The f*ck 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.
- [Jason groans]

[Andy] Ah.

They portaled the portal.

- [Jason] 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...
[breaks out laughing]

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
- [Jason] Yeah.

- and lemon water.
- Skinny Pop.

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

And we find out...

Well, that... Look.

- I... Hey.
- [crowd laughs]

[Jason] We're all staying
in the same hotel room.

We thought
it'd be fun and funny.
It's a f*cking drag.

- [all laughing]
- Are you really?

- Are you really staying?
- [Will] Yeah, yeah, yeah.

- No, it's nice. It's fun,
it's great.
- [Andy] 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 f*cking monster.

- [crowd laughs]
- [Will] Yeah.

- [Jason] But, but...
- And rightfully so.

- But the point is...
- [crowd laughs]

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

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

[all laughing]

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.
- [Sean] Aw.

[audience] 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?
- [Jason claps] 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?
- [Sean] Jeff Tweedy!

[Will] No!

[crowd cheering]

[Jason chuckles]

[Sean] 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.
- [Jeff chuckles]

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.

[all chuckling]

- 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!
- [crowd cheering]

[all laughing]

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.
- [Jason] Okay.

[all laughing]

- So...
- [Sean imitates stuttering]

Sean, let the robot speak.

- [all laughing]
- 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.

- [all laughing]
- [Jason] 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.

- [all laughing]
- And I'm pulling for you.

"How... how does music?"

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

- I not know things.
- [in a robotic voice]
"Processing."

- Help me, Jeff.
- [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.

[all applauding]

- 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--

[all laughing]

Uh-oh.

- Oh, my God!
- [all exclaiming]

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?
- [Andy] Yeah.

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

Your stage director said,

"There's three million people
watching, don't f*ck it up."

[all laughing]

Last year we would have
k*lled for that number.

[all laughing]

I was gonna say that
I had to teach myself

how to ignore the guy yawning.

- Uh-huh.
- That un-laughing
mother f*ck,

- I stare at him every time.
- [all laughing]

[Will] 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.

- [Will] Ah, yeah.
- Twitter is based on that.

- It's true.
- [Jeff] Like, that reality.

All right.

- [strumming guitar]
- [crowd cheering]

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?

[whistling]

[all cheering, laughing]

Let's forget about
The tongue tied lightning

Let's undress just like
Cross eyed strangers

[Sean] That was so cool.

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

- [all chuckling]
- [Jason] Wait, I still
got my shake in here.

Oh, God, it's probably warm.

Is this supposed
to be you guys?

- [Jason] I know, Granny Hayes
with the shades.
- [Will] Yeah.

- [all chuckling]
- 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
f*cking a big frosting.
I'm not like you.

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

- 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...
- [Will] 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.

[Jason] Hey, man, great show.

- [Will] Great show.
- [Sean] 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.
- [Sean] Yeah.

- [Jason] And just have them
move down the couch.
- [Sean] Yeah, and a writer.

- Huh?
- And a writer.

Look, he's so angry
about the writing.

"No, we don't f*cking
rehearse sh*t. 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.

- [Sean] Absolutely.
I have a couple of them.
- [Jason] 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...

- [Sean] Hands?
- Your God forks.

- You know?
- [all chuckling]

-"God forks."
- [Will] 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.

[producer]

- [Will] Oh, wow.
- [whines] Oh, my God.

[sighs wearily] Oh, my God.

Margaret, I can't.

Having an anxiety attack.

[producer]

Where'd you go, JB?

[Jason] I'm coming.
I'm just freshening my lips.

[Will exclaiming]

Wait, wait, wait, wait, wait.

[breathes heavily]

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

Nobody's gonna see it.

No.

[producer] You guys ready?

- Oh, my God!
- Yeah.

Trying to wake up.

I know. Me, too.

- Okay.
- [slaps]

- Okay.
- Oh, f*ck.

- Just have to get
excited about it.
- Holy f*ck!

- [slaps]
- [Sean laughing] 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.

[Sean] We're sorry
that we're running late.

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

- Oh, f*ck.
- [Sean screams] Stop it!

Stop, stop it. Stop, stop it.

[Will] Okay. So...

[Jason] 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.

[in accent]
Welcome to Chicago.
Something like that?

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

[in accent]
No flash photography.

- Right. And what else?
- [in accent] And put your
f*cking 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...
- [all] To SmartLess!

[Will] Run, run, run, run!

[crowd cheering]

Hello, Chicago!

[all cheering]

[Will] Wow!

[Sean] 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.
- [crowd] Aw!

[Sean] 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 f*ck it.

Wait...

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

Okay, so, wait.

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

[all laughing]

Wait. Did it matter
what kind of dinosaur?

Like, would you not
get turned on

- by a Tyrannosaurus Rex,
- [Sean] 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."

[all laughing]

[Will] Wait a second,
wait a second.

Just because we're back
in your hometown,

- you gotta tell the story...
- [Sean] 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.

[audience laughing]

- Um...
- [both chuckle]

Tonight, on a very
special SmartLess...

What the hell?

- [Sean] All right. So,
we're gonna get to the guest.
- [Will] 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.

- [Will] 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!

- [crowd cheering]
- Oh, let's go, let's go.

- Oh!
- [Jason] Wow!

Good to have you on here.

- Thank you.
- Nice.

- [Will] sh*t! Hey, man!
- Hey!

Thanks for having me out here.

- Hey.
- Sean.

Oh, yeah. Absolutely.

Where do you want me?
Right there?

- [Will] 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.
- [Will] Yeah.

[Mark] And these
are his shoes.

Oh, I got it.

Every now and then,
I pull 'em out.

- [Jason] Right.
- Like you should.

- Like I should.
- [Will] 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...
- [Sean] 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 f*ck
in the entire world.

[all applauding]

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

You remember the moment that
you were first a billionaire?

- f*ck yeah, I remember.
- [Will] Yeah, so.

[all laughing]

[Mark] 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.

[Mark] 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.
- [all laughing]

[Mark] 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?

- [Mark] At home. Right.
- [Jason] By yourself?

- [Mark] By myself.
- Hitting that F5.

Yeah.

You were just
by yourself at home

in your f*cking
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.
- [all laughing]

[Will] Oh, my God. Sean.

[Jason] That's good.

What did you guys, do this?

- [all chuckling]
- 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?"

- [Mark] Yeah.
- What was it?

- Basketball team.
- [all laughing]

How do you buy
a basketball team?

You write a big
m*therf*cking check.

- That's what you do.
- [all laughing]

[Sean] 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.

[all laughing]

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

Or where you wanna
put your money?

[Mark] 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.

[all applauding]

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

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

So, it's called costplusdrugs.com.

- Right?
- Yeah.

[Mark] 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.

- [Jason] That's amazing.
- Wow!

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

It's hilarious.

But... [chuckles]

Whenever I introduce him,
I go,

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

[chuckles] Now, will that be
on your list? Insulin?

So, to do insulin,

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

- [Mark] It's hard.
- Yeah.

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

[all applauding]

So, you're talking
to a dumbass.

- Confirmed.
- [Jason] 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.

[chuckles]

Never watched the show,
has he?

- [all laughing]
- I've... I've... I've...

[crowd booing]

Guys, I'm...

Don't... f*ck...

- [all laughing]
- They're f*cking
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.
- [Sean] Okay.

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

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

So, we can do it
street fashion.

- Scotty is here.
- [all cheering]

Stand up,
he's gonna be dead soon.

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

I know. I'm gonna die
from diabetes.

[all laughing]

- Oh, my God.
- Okay.

All right. So, here we go.

[audience member] Scotty!

[audience member exclaiming]
Scotty!

- [both] Shh.
- Shut the f*ck up!

- Shh, shh.
- [audience laughing]

- We're pitching.
- Okay, ready.

Hey, sharks.

[audience laughing]

My name is Sean.

And I'm Scotty.

[all laughing]

They're good.

And we're from...

[both] Hollywood, California.

And we're looking for...

[both] Two million dollars...

for two percent
of our company...

[both] Doggie Defence.

Yeah.

[Sean] When you're loading
the dishwasher,

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

[all laughing]

Ours does. Which gives us...

[both] Pause for concern.

- [all laughing]
- Oh, God!

Oh, boy.

Let me tell you a little...

[both] Tale.

We came up
with a fence barrier

that goes around
your dishwasher door

that deters your dog
from accessing the dishes.

[all laughing]

And with that defence up,

our dog is no longer...

[both] Barking up
the wrong tree.

[audience exclaiming]

So, sharks,

don't leave your dishes
in a rough state.

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

[both] Our pack.

[hi-fives]

[all applauding]

Whoo!

- Sean...
- Yeah.

That was really weird.

[all laughing]

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.

[all laughing]

- [Mark] I got it.
- [Sean] Okay.

I just wanted to hear you
once say...

- I'm out.
- [Sean] That's right.

- [Will] Oh!
- [Sean] 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.
- [Will] Mark Cuban!

[all applauding]

[Mark] 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.

[all cheering]

[Jason] 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.
- [all laughing]

- Yeah.
- Not dead yet.

- Not dead yet.
- No.

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

- 15 years.
- Whoo!

[all applauding]

Scotty, before you guys
were married,

did you know about
the dinosaur story?

- [all laughing]
- No.

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

- [Will] Right.
- But not before
we were married.

- Yeah.
- [Will] Huh?

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

[all chuckling]

No, this is a fair question.

No. No, of course. So...

Scotty, how did you
used to masturbate?

[all laughing]

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.

[Jason] 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!
- [all cheering]

[Jason] Thank you, Chicago!

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

Thank you.

Yo, where should we go?

[Will] Right here.

- [Jason] I can't
reach there though.
- [Will] I can do it.

- [Jason] Oh.
- Oh, God.

We got you.

[Sean] You're left-handed.

Wow. You really
climbed up there.

- [crowd cheering]
- [Jason] Hey!

You guys, thank you
for coming out.

[Will] Hi, guys. How are you?

Thank you so much
for coming, you guys.

Here we go!

[Sean chuckles]
I'm gonna eat that in the car.

Turn around.

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

- [Sean] So sweet.
- [woman] Thank you so much.

[Will] 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.
- [Sean chuckling] I know.

They are famous.

- [Jason] No?
- [Sean] 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.
- [door closes]