SmartLess: "David Letterman: LIVE in Brooklyn"

Hey, listener, and welcome to SmartList.

Before we get into this incredible episode,

I want just a moment of your time

to set the stage a little bit.

Sean and Jason and I went on a SmartList tour last year

where we recorded 10 episodes live

in front of thousands of our biggest fans

from Brooklyn to Los Angeles, and guess what?

Right now, there are more live episodes

from our tour on Wondry Plus that you can listen to.

You can listen to these episodes four weeks early

and add free on Wondry Plus,

after which you can hear them for free

wherever you get your podcast.

Find Wondry Plus in the Wondry app or on Apple Podcasts.

All right, welcome to SmartList.

Hey, let's do that thing really quick

where we finish the sentence.

We do one word at a time.

No, no, like we do one word at a time.

I'll start, I'll start, ready?

We, no, ready, go.

We are so excited to be here.

Oh, Sean.

Come on, let's go.

This is like what is taking a fuckin' road trip with you.

Hey, kids, let's build a story together.

How about we just go do the friggin' live podcast?

Great.

Yeah, let's do it.

All right, guys.

Welcome to SmartList.

Wow.

Wow.

Wow.

This is so nuts.

Brooklyn!

This is just ridiculous.

I like pulling an Oprah.

I like pulling an Oprah Winfrey and go,

take a seat, take a seat, take a seat.

I know, I know, this started, this was a bit.

We started this as a bit.

Yeah.

And now we're here in Brooklyn.

With all these beautiful people.

I know, I love it.

Thank you for coming.

Thank you for spending $5 a ticket to come see us.

We really appreciate it.

But good God, well, they're here.

I guess we gotta do this.

I know.

Yeah.

Everybody all back there.

Buckle up, Cynthia, we're really low.

I'm sitting here.

Yeah, you're gonna sit there.

You're gonna sit there.

Yeah, you're gonna sit in the middle,

because I get, I get, tonight it's my guest,

so I get the middle.

Why is that good news?

Why is that good news?

That's not always good news.

I will tell you, I am very excited about my guest tonight.

My heart is pounding, pounding.

And it's not just the diet Red Bull.

Now we've all had a lot of Red Bull

and because we had a long night.

Oh my God.

Oh, Jesus.

So we got stuck in, where were we?

Boston yesterday.

And we were, our flight was supposed to leave

at 10.30 after the show,

and we ended up leaving at five this morning,

six this morning, something like that.

45 minute flight took us eight hours to get here.

Eight hours.

So we've had like three hours of sleep,

so we are getting the best version of us.

But,

but the best part is our amazing,

incredible director, Sam Jones.

Yeah.

We're stuck on the plane

and we're all kind of just really quiet,

trying to catch any kind of winks we can.

And then we hear this.

Oh God, yeah.

And by the way, where he's like,

I didn't get any sleep.

We're like, no, no, no, you're the only one who got sleep.

Yeah.

None of us.

And then when we get to the hotel,

they always make fun of me

because I always have my kind of, you know, my things.

Like when you travel, you have your things.

And so I always ask for a fan and a blanket.

I need an extra fan.

So every time we pull into a,

Yeah, let's not gloss over that.

Let's not gloss over.

Every time we pull into a hotel,

Sean, there's always a, like 20 minutes later,

there's like a knock on the door

and a guy shows up with a fan and a big blanket.

And we're like, no, wrong room.

And then Sean shoots up, no, no, no, that's me.

Cause we're all staying together.

Do we mention that?

We're staying in the same room?

Yeah.

We're all in the same room.

It's all for this stupid ass show.

Where do you see it?

It's such a mistake.

Actually, it should be noted,

you wanted to stay in the same room.

Well, I thought it was like, well, if we're going to do it,

let's get full stupid ass, you know?

So Jason, so Jason's like,

listen, we're all going to stay together

and we're all just going to be,

and we can just 24 hour access to the cameras,

six hours into it.

He's like, fuck this.

Yeah.

It's a nightmare.

It's your idea.

Cause I'm not usually, this is, I am peeking right now.

I'm usually in such a bad mood.

Am I not a moody guy?

Yeah, you're very, very moody guy.

Every morning, every morning,

this coming straight at me,

just his hair is about eight feet high

with the bed head, with the cup of coffee.

So fucking angry.

He's coming right at me.

And he shuffles too.

You know how he shuffles?

He kind of like, he walks like this.

No, I'm not exaggerating.

He walks like this and he looks like,

he looks like all of his bones are so brittle.

Like he's about to snap like this.

Is that true?

It's true.

Daddy's back hurts.

I know.

A lot.

What else?

I don't know.

What else?

So much else.

Should we just get to the guest?

Yeah, let's get to the guest.

Let's get on with it.

All right.

It's your guest.

All right, granddad needs notes too.

Gang dash.

We've been going to different cities

and in each city,

we are trying to invite a guest

that is part of its fabric, its spirit,

its soul.

This guy, so now you know it's a man,

checks the boxes.

He is also...

Giuliani.

Oh, no.

Anan...

Giuliani.

Wait, no, I was saying...

Don't turn them against us already.

Wait, I may have skipped a sentence.

Hold on a second.

Oh, God.

Gang dash.

Like that.

We've been going to different cities

and in each city, we're trying to invite a guest

that is part of its fabric, its spirit, its soul.

This guy checks those boxes.

He's also an enormous hero to each of us.

He is comedy royalty.

I know exactly who it is.

Bullshit, you don't know who this is.

I know exactly who it is.

Don't guess it yet, hold on.

Mouth it to me.

Hold on, don't let me see it.

And he is the undisputed best at what he does.

Right?

Keeps going like this.

Martin Short.

Martin Short.

Short.

Are you finished?

Sorry.

Gang dash.

Thank you, Sean.

All right.

He's the undisputed best at what he does.

No one better, period.

He has 52 Emmy nominations to prove it.

Along with 12 wins,

he's got a Kennedy Center honor, a Mark Twain award,

but in the last few years,

he has selflessly chosen to stop everything

and fill in for the recently deceased Santa Claus.

Will, Sean, Brooklyn,

please welcome Mr. David Letterman.

Whoa!

No!

Come on, Dave.

No!

Thank you.

Oh, no.

Whoo!

Whoa.

Hi, Sean.

Very pleasure to see you.

Jason, very pleasure to see you.

Will, all my best, my friend.

Nice to see you.

Oh, my gosh.

No, no, no, no, no.

I don't know, where do I go?

Get there.

No, get there.

I don't know.

Thank you very much.

Hi.

To Riffin.

To Riffin.

Wow.

Thank you.

What a lovely thing and what a beautiful theater

and thank you and thank you again.

That was delightful.

I was, holy shit, right?

Yeah.

I'm sitting backstage listening to you guys.

Thinking about the mistake you made.

No, and all I can think of is,

I hope this doesn't cut into my time.

Yeah, sorry.

We have run a little long.

Let me get to question eight.

Oh, my gosh.

Oh, this is keen.

First of all, before you get into the question,

it's so great to see you.

Thank you for inviting me, please.

Yeah.

Yeah.

It's...

At risk of embarrassing you,

I should say that,

and I think I speak for Sean,

but it is such an honor to have you here.

You have always truly been one of my...

Oh, please.

I know, I know.

Oh, please.

And I've done your so many,

and I've told you that before,

but it's true and I'm so delighted that you're here.

I can't believe it.

Oh, God bless all of you.

I would just like to add that,

he said he'd speak for me,

but I've never said anything like that.

Oh.

Well, let me...

I have a rundown.

I have my own sort of document on you guys.

My dossier here.

When you were first on the show,

what I remember about you,

I think you were smoking.

Yes.

Were you really?

Yeah, I think you were.

Like I was going in and out of smoking,

and you would check in on my various appearances

as to whether or not I was smoking at the time.

You didn't smoke on the show, though.

No, I never smoked on it,

but I did do...

You liked it when I went

through my various smoking positions.

Yes, yes.

Which were...

I told you I had quit,

but I missed doing the like...

Me?

Yeah, yeah, sure.

Like that kind of stuff.

Yeah, yeah.

I mean, that was the hook upon which you were booked.

Yes.

Yeah.

I get it.

And extremely funny, and Toronto.

I remember that about you.

Yes, thank you.

Now, yeah.

And Sean, the last few times you were on the show,

you were doing a musical across the street.

Promises, promises, hold for applause.

Yeah.

Yeah.

And I don't know if it was between shows

or before the show,

but you came on with such enviable energy,

such good-natured, likeable excellence as a human.

That's the Coke.

Yeah.

That's very nice.

And...

Ha, ha, ha, ha!

Whenever we would be talking after the show,

the comment was always,

why doesn't Sean have his own show?

Well...

Like a talk show.

I know you've had shows.

Well, that's so nice.

Right?

I mean, that would be fantastic.

That's...

You thought about it?

Yes, I thought about it.

That's very kind of you.

And if I ever did it, here we go.

You are one of the biggest reasons why I would do it.

The biggest.

Yeah, you are such a huge influence on me

and so many people.

I know you hate that,

and you're like, where do I put it?

No, that's true.

But it's like, it's really, really true.

You are what he said in the opening,

a hero of all of ours.

Thank you, and of course, shit.

Thank you.

Now, here, now I'll get to you.

Now, you were on the show many, many, many times.

And in the...

I know you won't believe this,

but we had pre-show meetings.

And it was...

No, not with me.

No, not with you.

Everyone was very excited.

And then you would come on,

and...

I'm just a big letdown.

Wow, can the guy talk?

And, I mean, really, we only had an hour show.

What?

And then he was so...

He had so many stories.

And he told them so well,

and he had them memorized.

It was like talking to Charles Dickens, for God's sake.

And then, at 10.45,

the people would be the broadcast senator editing

because he had gone so long.

So that's what I remember

about the appearances of the three of you.

You were in a blackout, weren't you?

Most of the time?

Oh, I'm in a blackout right now.

Now, this is fascinating to hear you say

because I've always wanted to ask you this,

or anyone that I have been on a talk show with.

Because, so, for those that are for Tracy.

Tracy.

Tracy.

Tracy.

Tracy, yes.

Yeah, Sean's sister in Wisconsin.

Sean's sister in Wisconsin doesn't understand show biz lingo.

Sometimes we gotta fill her in on the inside baseball.

So, there is a pre-interview that a guest usually does

so that in the absence of a conversational skill,

you have a set of pre-determined questions

and ballpark answers so that the host and the guest

can have a palatable interview.

None exist on this show.

None exist.

None exist.

Now, he's in that regression.

How good like a robot.

Is it?

So, now, I, because I, like all of us in this room

and across the planet, are a huge fan of Dave Letterman,

you wanna make sure you got your stuff together.

So, I'd work on, what could I possibly do?

What's funny that's happened in my life

in the last few weeks?

So, I've got some stuff to say.

He's doing it now.

Yes.

Yes.

So, I would have these stories

and I thought I'm being responsible,

cause by the way, I remember watching you do an interview,

maybe it was 60 minutes or something,

where they would say to you,

what constitutes a good interview?

And you said, and I never forgot it,

it drives you nuts when people come on the show

and they think that you are lucky to have them

sitting in the chair when in fact,

they're lucky to sit in the chair

because they're trying to promote something.

Yeah, I mean, we're really, I don't know,

I just got a cue from the stage manager.

So, I always wondered if I went on too long

and now he's telling me I did, all those years.

But they all know, they listen to the podcast,

so they know you go on too long

and Dave knows you go on too long,

but we all love you, Jason.

Yes, we do.

But, now, you also, some of your colleagues visit

with a guest before they come out,

you never did that one.

They never would do that, no.

I love that, because that was for my name.

So, there was a question 10, 15 minutes ago,

are you gonna go down and say hi to Dave?

And I was like, well, no, he never did that

with any of his guests, I think.

Thank you.

And so, I probably shouldn't,

was that a good decision?

Yes, it was absolutely, in my case,

I can't speak for the world,

but in my case, that was a good decision.

Why?

Because you're down, so 10 minutes ago,

you're down in the dressing room, what are you doing?

Everything I know about, well,

that's none of your business.

But, everything I know about running a talk show,

I learned from Johnny Carson,

and Johnny Carson, he never came back.

He was the guy before Jay Leno.

Jay would come back into the room,

but Johnny never did.

Jay, he understand, it was like the Rotary Club with Jay,

but Johnny would never come down,

because he always felt like,

whether I know the guest or do not know the guest,

I want the, oh, hi, welcome to the house moment,

and that initial electricity, or lack thereof,

should come naturally, so that's that.

That's the point of the whole show.

Can I ask you this, what was your,

I mean, I'm sure you remember,

what was your first meeting like with Johnny?

What was that event?

Was that because he was hiring you to do the show?

Or was it just an appearance, like a regular appearance?

Yeah, the first time I was on the Tonight Show as a guest,

and it's interesting because we're talking about Johnny Carson,

had we been talking about Johnny Carson 30 years ago,

the room would be full of a different kind of electricity.

But for those who didn't experience that,

he was, I think, the best ever at the show business,

late night television talk show format, without question.

And if you look at what he did now,

the consistency of what this guy did,

I mean, it wasn't once a week,

it was night after night after night, solid.

I will watch reruns with my husband,

I'm gay, Dave, I would watch,

Still?

Yeah, still, yeah.

I am taking, every medication is not working.

Okay, okay.

Oh my God, this is awful.

I know it's an awful one.

We need stuff to cut, Dave.

So Dave, me and Scotty, a lot of times,

check out old Johnny Carson episodes,

and it's amazing how long he spoke to the guest.

It was like a 20 minute, 30 minute interview,

and are you happy that you didn't have to do that,

or would you have preferred to have that time?

Well, that's an excellent question.

I think you always would like a little more time,

especially if you're enjoying the moment, the guest.

But the thing about Johnny, he just was always Johnny,

and it didn't make any difference who the guest was,

or what was going on.

You just wanted a chance before you went to sleep

to visit with your friend, Johnny.

And he did that for 30 some years,

and there was, I never saw the guy break a sweat,

I never saw him miss a beat.

But people feel the exact same way about you.

They do.

Well, how many, how many-

I'd like to see the paperwork on this.

How many, and we're gonna get into Jason's appearance

on Johnny Carson, his first one.

Oh yeah, yeah, there you go.

It's great, and I wish we had an image we could pull up,

because it's tremendous.

This is great.

How many times did you do the Tonight Show with Johnny

before you then, he sort of anointed you

to do the late night show?

Well, you guest-hosted a bunch, yeah?

Yep, a few times, maybe a couple of dozen times

guest-hosting and appearing as a guest on the show.

And then we got the 1230 show,

which Seth Meyers now has,

and Conan O'Brien had that show for a while as well.

I want to tell you something.

I've been listening to the show.

Come on.

Yes, and I had it on when Ryan Reynolds was on.

God bless Ryan Reynolds.

And-

A great Canadian.

And I started thinking, oh, this is,

I have to talk to him for the little Netflix deal,

and I listened to him on your show,

and I thought there's no point.

This is the best piece of entertainment,

not in a film with Ryan Reynolds and friends.

I just, it depressed me.

So today I thought, okay, I'm gonna be there in Brooklyn,

and I'll listen, I'll just listen to another one.

And it was Barry Sonnenfeld.

Yeah, yeah.

Oh, right, I know, and he was on your show a lot.

Yes, and we loved him.

Talk about a guy that had to have a little editing.

Oh, yeah.

Oh boy.

They were still working on his last segment.

You know the story about his getting,

when he's first started in pornography

as a young cameraman,

and that story, which was about five minutes

that our show was 40 minutes,

and we all agreed that even for us,

we thought there's no way.

Yeah.

Oh yeah.

My mom can't hear this story.

Yeah, we pulled it out, no one will ever hear it.

It's the most repulsive story you've ever imagined.

It's unbelievable.

We rarely do that.

Yeah.

So the same thing with this,

I know Barry Sonnenfeld, as Will mentioned,

and I couldn't finish listening to him

because it was so good, and I thought,

oh, I'm gonna go out there and just dump

all over their show.

And I tell you what I love about it

is the theme music for the podcast.

All right.

Yeah.

It's catchy.

They haven't put the bar too high.

No, no.

It's dead.

Yeah, you know the show can live up to that.

And then the Barry Sonnenfeld one, you were in London.

Yes.

And I'm thinking, this is the example

of why radio ruled the world before television.

Instantly now, I'm envisioning myself being in London,

and you guys, I assume, were on the West Coast.

Didn't really come to mind.

In slippers.

But Will in slippers, slippers and PJs.

But I was delighted by it.

But then again, the interview with Barry Sonnenfeld

was so good, I couldn't finish that one either.

I'm sorry.

Now, are you loving doing long form conversations

as opposed to the 10 minute sprints?

Well, there's two different things here.

Yes, the longer, the better.

But you know, they're two different machines.

The talk show is, I understand you had trouble

on the airplane coming in from LA.

That's the talk show.

Yeah.

And then the longer form is,

have you ever seen an airplane?

That's a whole different story.

Ha ha ha.

Ha ha ha.

Ha ha ha.

Ha ha ha.

So, it's a little roomier in that house.

And we will be right back.

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All right, back to the show.

When you decide who you want to talk to,

are you, because like for us, it's obviously,

it's see if hero X, Y, or Z is interested in talking to us

and or who could we learn something from

because we are less than smart.

How do you go about deciding who you want to talk to?

It's the same, everything is a compromise

and sometimes you're pleased with a compromise,

sometimes you have to take one and wait your turn.

It's not, that's the most difficult part about it.

I'm guessing you gentlemen perhaps do not have the obstacles

that we sometimes have getting guests for our show

because, hang on.

No, no, I want to say, everybody I knew when they,

because people, they're surprised to see me.

They say, well, what are you gonna do?

And I mentioned this, oh my goodness.

For some reason, people really embrace the idea.

I don't get it.

That's a good point for some reason.

That's the part that sticks out.

It's so beautiful because it's so organic

because I believe you are friends

from a previous existence.

Yes, yes, we're three, and we did start it genuinely

so that we could spend time with each other.

During COVID before the pandemic.

That was quite legitimate.

And we did set the bar very low.

It was very DIY and it's still,

for all intents and purposes,

is the way we do the show, the way we put it together.

Do it myself.

Do it myself.

Thank you.

And we try to keep resetting the bar as low as possible.

And that's what I wish I could go back

and tell my parents in high school

how important it was to keep the bar low.

That's what I was building to this.

You know what I mean?

It's like being in the Admirals Club,

waiting for a flight,

and you hear three people genuinely interesting

and friendly talking to one another.

You had ratings to tell you,

oh, there are people watching the show.

We literally opened up our laptops again

and our pajamas doing this.

Had no idea if people were listening to this.

And then you nice people bought tickets to a tour,

which was the only verification

we had that people were listening.

So thank you very much.

It is absurd.

Dave, I, you know.

Oh, search for it.

Oh, let's pull it over to the side.

This is great.

You really, really wanted it, man.

It's not, you know, everybody.

Let me help you out, favorite color.

Ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha.

You know, Dave, I don't know if you know

that Sean was nominated

for a Host of the Year.

Oh, Host of the Year.

Host of the Year, iHeartRadio podcast,

Host of the Year.

And again, not to belabor it,

but Sean sent Jason and me a text saying,

hey guys, congrats.

We were nominated for this award.

And the second sentence highlights the fact

that he was nominated for Host of the Year,

to which Jason and I responded,

well, congrats, I guess.

Yes.

Yeah, he didn't read the body of the email,

just the headline that we'd gotten a couple nominations.

Well, on the most joyous part of that whole thing was,

you losing.

That's right.

You lost.

Who is Host of the Year?

Who is Host of the Year?

I have no idea.

No, no, no, seriously, who won?

I'm being serious, I have no idea.

Well, how do you, you're a nominee, you should know.

Yeah.

You've been nominated,

do you know all the people in your category?

Yes, I do.

Ha ha ha ha ha ha ha ha ha.

Oh.

You're all pinned up in your way.

Yes.

I swear to God.

And most of them are John Stuart.

Ha ha ha ha ha ha ha ha.

You do, you know, the, the, the grind of a talk show

that you, the David, the late night with David Letterman,

everybody knows the grind is just,

You work your balls off like five days a week.

You're always there.

Everyone knows that.

And because of that, you tend to have a more reclusive life.

And we all, people are kind of amazed when you appear

anywhere because like, oh my God, Dave,

it's like a magic trick.

It's like somebody pulls you.

Respond to these accusations that you're a recluse.

Right?

Oh my God, he's walking upright.

But so what do you think has changed

since your show, you chose to end your show from then and now.

Have you evolved into, other than your Netflix show,

other than business-wise, what do you reflect upon now

and think differently about?

Your Honor, could I hear the question again, please?

Is that what I sound like?

I'm sorry.

Oh no, no, that was not even close.

That was better.

So it's worse than that.

That was Reader's Digest compared to you.

Well, I'm going to start, while you're answering,

I'm going to start studying my questions again for a second.

I don't know exactly what to say.

Yes, that's OK.

That's OK.

I just think like, are you more open to things

that you weren't now that you may have not been?

Well, I realize that, and perhaps the three of you

feel the same, and I hope not, when you have a show,

and I don't know that it's like that now,

but I was so single-minded that I shut out a lot of other

experiences in my life that I should have been enjoying.

Well, this is what I'm talking about, David.

Well, I wish you had said that.

Easy, but just stop pressing him.

Why are you making this so contentious, Sean?

If you want to lay down for the rest of the therapy,

I can go sit over there.

But I will say that many, many things that are more important

to me now than I knew they were when I had a show,

and I think that's lopsided.

So that's a regret of being on the air that long ago.

I feel like we're skirting around family.

Let's talk about family, Dave.

OK.

No, let's talk about your family.

What about your sister?

Thank you.

Sure name's Tracy.

You want to come to Madison?

I've been to Madison, University of Wisconsin.

Beautiful, yeah.

Yeah, we're going there.

Now, I used to love you talking about your drive

to work in your monologue.

Did you drive here today?

I rode here.

You rode here today.

Did we send a car?

Someone did.

OK.

Now, do you?

Well, sorry, I thought you meant a motorcycle.

I legitimately did.

I wish.

Oh, you know how I got here?

My Harley.

No, no.

You got motorcycles.

And I wish it was a Harley.

I came on my motorcycle, my Harley,

Davidson today.

That's not true.

No.

No.

But you've got some.

Yeah, but when you get to be my age,

every time you get on one, you think,

oh, I shouldn't be on this.

Right.

And so they are less ridden than they used to be.

Do you still like driving fast?

Yes, I do, but I don't anymore.

I lost my license for a month because of driving fast.

And that took it right out of me.

Because?

On the Merritt.

On the Merritt Parkway, yes.

Yeah, that's great.

It's a great road to drive quickly on.

Well, how fast?

Fans of Connecticut Highways.

Hey, yeah.

How fast were we going?

The fastest I've gone in a passenger car,

there's two figures.

There's the European number, and then there's the Long Island

Expressway number.

Long Island Expressway 140.

Autobahn 150.

Nice, nice.

Now, don't you agree?

Nice.

I like it a lot.

I think that makes a lot of sense, right?

It makes no sense.

There's no speed limit.

Jason, tell them, you're a very,

Jason has won the, no, come on.

Cheesy celebrity race.

You won the.

Oh, the Toyota Celebrity Grand Prix.

You did that, didn't you?

I never did it, because I knew I would make a fool of myself.

But you won the race?

I did pretty well.

First, one year, second, and third.

I don't like to brag.

Wow, so you were on the podium three years in a row?

I don't know if they were consecutive.

Yeah, I know.

Come on, come on.

And, Jason, you're not going to switch the subject.

And in a non-celebrity race, you also partook

in a professional race in the Poconos, am I right?

Yes, we did Lime Rock and.

And then the Poconos, I got in a spill,

because some dingbat got in a crash in front,

and then I had to go through the wreckage, flipped over,

and the wheel wheel came up, the wheel came up

through the wheel wheel, smashed my ankle, broke a bone,

only broke a bone I've ever had.

And then I said, I'm going to leave this

to the professionals, I'll go back to the Cheesy stuff.

Well, he illustrates exactly what kept me

from doing this sort of thing.

He's exactly right.

Now, were you on the oval at Poconos?

The Tri-Oval.

The Tri-Oval.

Yeah, yeah, yeah, yeah.

You can get some speed going there.

But speaking of speed, don't you think.

What kind of car were you in?

This was a sport truck series.

So it's pickup trucks, but lowered.

It's not, yeah, see, it's not that impressive.

God, that's so unbranded.

There is nothing, right?

Nothing impressive.

Nothing more exciting than watching trucks race.

Whoa, where do I get my season pass?

So from the excitement of car racing

to something truly mundane, I really want to know,

what'd you do today?

What do you do every day?

That's what I'm interested in.

I want to know what's just a normal day for Dave?

Are you an early riser?

Let's start there.

No, not an early riser.

I go to bed late.

I stay up late watching climbing movies.

Oh, no, no, shut up, Will.

Wait a minute.

Will, oh God, he loves any of the foreign crime shows

on Netflix with subtitles.

He'll talk to you to your ears bleed

about that or climbing stuff.

No, but wait, what about solo?

Did you see solo?

Free solo.

Free solo, sorry.

This is years ago for me.

Han Solo.

No, no, no, free solo, free solo.

I'm down to watching Slovakian people climb their way

through the Tatras in English subtitles.

And I don't know why.

I know Alex Honnold like he's a member of the family.

And I can't stop watching him.

That's the free solo guy, Alex.

Yeah, he's amazing.

He's been on the show, eh?

Hey.

No, he's the Canadian.

That's the Canadian.

Sorry.

Now, there's something about Mount.

But he should be on the show.

He should be on the show in the 100 foot wave too.

Sorry, just that's incredible.

In Portugal, yeah.

Anytime you see these people who are doing incredible things

and the other guy who was, yeah, 14 peaks.

Excellent, yeah.

And we're good.

No, there is something about Mount Everest.

Did you get heckled a lot last night with the businesses?

Yeah, well, we did.

I mean, if the sound of seats emptying counts as heckling,

I'm so sorry.

Forgive me.

Currently, there were quite a few people that left.

Let's go, Carol.

It's your first, Ellen.

There is something about Mount Everest

that's like a magical draw to me.

Do you have a Mount Everest draw at all?

Well, I know quite a lot about Mount Everest

from the two dozen films I've watched

about climbing Mount Everest.

Would you?

Oh, God, no.

Like, what do you like about it?

I don't know.

I just don't know.

Somebody seeing a challenge through

like that kind of a hefty lift.

Yes, the scenery, typically lovely.

And the kind of things I will not see probably

in my lifetime, regrettably.

Yeah, I felt that way like when I went to Paris

for the first time.

I was like, well, there's the Eiffel Tower.

It's just like every movie and postcard I've got it.

I'm ready to go.

Well, when you're climbing Mount Everest,

every film about climbing Mount Everest,

I'm sorry, did I lean on your laugh there?

No.

It wasn't going to get higher.

So you would not, what about your space camp?

No, no, good Lord, no.

It's just a helicopter ride.

No, it's not.

Helicopters can't fly above 20,000 feet

because the air is so thin.

No, no, no, but they do rescues that are higher

than that, right?

No.

No?

No.

God.

Rescues above that elevation are rarely successful.

But you get into what they call the depth zone.

The depth zone, yeah.

Where your body starts consuming itself.

Yeah.

And the air is so thin and you lose your voice

and you get dizzy and you get blockheaded.

And I heard one man describe, he was coughing up tissue

from his own throat.

So you see why I can't live without him.

David.

That's great.

Now you don't do climbing, right?

I don't do climbing either.

My dad climbed Kilimanjaro when he was about 73,

which is not huge yet.

Oh, it's a big deal.

But it's pretty big.

19,000 feet.

What?

Yeah.

I always tell these guys stuff about my dad

and they're like, what?

And I'm like, well, you never, and it turns out they never ask.

Well, Kilimanjaro.

My dad wrote a book during quarantine.

He wrote a novel.

That you bored us with earlier.

Yeah.

And fiction, non-fiction?

Fiction, but based on a true story.

You guys never ask about my dad.

Well, it's not a happy story.

How do you describe a black hole?

Like, you know what I mean?

Well, it's just a tire screeching.

Speaking of speeding away, yeah.

Sean, he invites this day.

By the way, just in case you think we're being cruel,

he sent me up for that.

I feel like I came on a bad night.

I know you did come on a bad night.

I wanted to ask you just to get out of climbing for a second

and go back to just because I'm fascinated with when

you started and you started doing late night.

And in fact, I think you, and correct me if I'm wrong,

started actually in a daytime show in the hosting capacity.

I used to watch it all the time.

It was on NBC at like 9 in the morning.

Yes.

Yeah.

I used to watch it as a kid.

I was fascinated by you.

Like, because nobody was doing that kind of comedy,

especially during the day in the morning.

You started, and you got that job coming out of,

you were a stand-up for many years.

And what was that transition like?

Did you know at that moment you were saying goodbye

to your stand-up career and that you

were going in a different direction?

Yeah.

In my day, those days, a long time ago,

it was much easier to know what you were going to do

and know how to get there.

And so I knew that if I wanted to get a television show,

I had to go to California and start doing stand-up.

And then you get on The Tonight Show.

And then if you're lucky, other things happen.

And that's exactly what happened for me.

So where did doing the weather in Indianapolis

fit into that plan?

That was my nascent television career.

So that was the door that was open

happened to be the weather door?

Yes.

Yes.

And did you enjoy that?

I just enjoyed.

First of all, not a meteorologist did not

know anything about the weather.

Still really don't.

But I was like 20 years old and they put me on TV.

So that's kind of what I enjoyed.

And then I knew that this is what I wanted

to do with my life, not this, necessarily.

No.

Nobody.

Nobody wants to do this.

It's only about 15 minutes more.

And so then I went to California and I got this show

and we moved to New York.

And it was like Sean said, it was 90 minutes live.

And within a month, the NBC Daytime Television Network

collapsed and affiliates were running.

They were selling their stations.

They were burning things.

Insurance people were investigating

all because of me and my friends.

And I don't know how you guys felt about your entree

to show business, but you made a life of it when you were a job.

I'm trying, Dave.

No, no, but I mean, along, you were born to it.

Yes.

How old were you?

Sorry, Jason.

How old were you, your first professional engagement

in show business?

Little house on the prairie.

Little house.

Does that, that he knows that?

He knows that.

Does that, how does that feel, Jason?

I'm, it's going to take me a while to get over that.

I remember seeing you on a couple of Silver Spoons.

Oh yeah.

Yeah.

Yeah.

But Dave, did you think that you were going to do,

when you moved out to California as a standup,

did you think that you, did you have aspirations

to be an actor, to do a sitcom?

Was that something that was, no.

No, what, what I wanted to do was.

Who wants to do those?

Me?

No.

No, I just knew I wanted to, I wanted Johnny Carson's job.

Right, right.

So you always knew that.

Isn't that, if not his job, a job like that.

Yeah, but we talk about that all the time.

We talk about that a lot, about like if you,

when you're that young, knowing exactly what you want to do,

that your odds go up that you will achieve that,

because you're so focused on a goal, isn't that?

But, but what made you, so, so, so, I don't know.

I'm going to yes and it.

I'm going to yes and it.

Johnny, Johnny was so good at so many things,

and one of them was his, his kindness and conservative

sort of approach to certain things.

He was very unthreatening.

Sexy indifference.

Sexy indifference.

Is very, it was very unthreatening in the best way.

Now, your sense of humor has got this incredibly awesome,

hilarious edge sarcasm, dryness to it,

which is near and dear to my heart.

What made you confident that you would be able to make

a career of that without America being afraid of it?

He's trying to say, why did you think you could be in showbiz?

Oh, thank you.

Well, I, I was, I had horrible grades in school.

I knew I wasn't going anywhere academically,

and I had a speech class, my sophomore year in high school,

where the first thing you had to do in speech class,

stand up and give us an impromptu five minute

introductory speech.

I did that, and when I sat down, I realized,

oh, I know exactly what I want to do.

So, the schooling of it made no difference,

and then later I figured out a way to do that.

So, as you point out, a rare comment on your part.

Yep.

He does listen to the show.

It's amazing.

It's so flattering.

It's, and I feel bad for a lot of people who just don't know

what they want to do, because if you do know that,

it's a true gift.

Yeah, I agree.

But you were able to take that sense of humor,

and you do your show, and somebody sits down in that guest

chair, and they're not being a good guest,

and I'll bet that incredibly sharp,

caustic sort of sense of humor in the best sense of the word,

starts to fire, and you have to start the self-edit of,

how nasty can I be to this person?

Sure, yeah.

Because they deserve it, and America that's watching knows

they deserve it, but you've got to kind of calibrate it.

What is that process?

Well, you wait really quick.

One of the funniest examples of that in history

is the walking phoenix, when you just couldn't get anything

out of him, and I think your line was,

I think your line was, well, I'm sorry,

you couldn't make it tonight.

Ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha.

Cute.

We'll be right back.

In the first part of the 20th century,

the Hilton family had a lock on the hotel

industry by offering upscale service at a modest price.

The company was expanding fast and buying up

iconic properties across the country,

like the plaza and the Waldorf Astoria,

but their unchallenged rise wouldn't last.

An ambitious Mormon named J.W.

Marriott decides to pivot from restaurants to hospitality,

and he's after Hilton's business,

developing modern hotels across the world,

but both the Hilton and Marriott families

will have to contend with their share of drama

in finding a successor.

While also fighting to stay solvent in a high-stakes

business.

Hi, I'm David Brown, the host of Wondery Show Business Wars.

We go deep into some of the biggest corporate rivalries

of all time.

In our latest season, Hilton and Marriott

are in a race to expand globally and secure

the loyalty of fickle customers.

Make sure to follow Business Wars wherever you get your podcasts.

You can listen ad-free on the Amazon Music or Wondery app.

And now, back to the show.

And then the opposite would be true.

The opposite would be deep, but he did the nicest thing

for me once.

We're doing the interview, and I said something

that was unkind to someone in my family.

I thought it was funny, and I could say it,

because they were in my family.

And the audience roared with laughter.

We go to commercial, and then Dave leans over and he goes,

so what we're going to do is I'm going to reintroduce you.

You're going to come out.

And we're going to cut that career-canceling comment

you just made.

And I said, what are you talking about?

Which part?

He goes, you remember when you called such and such

and such and such, and he's like, but they love that.

He goes, you're not going to love it.

We're going to redo the top.

And I came back, he reintroduced me,

I came back, we reshot the whole beginning.

How many times have you done that was such a nice thing you

did for me?

Not.

That was the only time you ever did that.

I didn't have to do it much.

Had to do it quite a lot with myself.

Truly?

Oh, yeah.

Because really?

I was going to ask you, do you remember those vividly,

the top, do you have the top 10?

No.

Why, I wish.

And I'm not asking.

Sure.

Yeah, we live in fun times.

I remember this was a thing, Sarah Palin.

Near and dear, near and dear.

Remind me.

Remind me.

This was a joke I told Sarah Palin and one of her daughters

had been at Yankee Stadium.

Already funny.

And I think she had two daughters at the time.

I don't know the state of the family now,

but at the time, I think there were two.

And there was a younger one and an older one.

I assumed that it had been the older of the two.

What's the matter?

I'm loving it.

I'm loving every morsel of it.

Keep going.

So I assumed it was the older daughter.

And the joke was some clumsy suggestion

that Alex Rodriguez had made a move on the daughter.

Later, I find out, to my embarrassment,

that it was, in fact, the younger daughter.

This joke entirely inappropriate.

So now, I remember that.

So she was south of 18.

I don't know her age.

I just know that I had made a mistake.

So I thought long and hard, and we had meetings on it,

and we crafted an apology to Sarah Palin and her family

and to everyone at Yankee Stadium.

Did they respond?

Well, here's what happened.

Now, I do the opening, and you can just

feel the leaden sense of dread in the theater,

because I'm about to pour my guts out, apologizing.

And it deserved an apology.

It was stupid, ignorant, more than stupid.

Which is better, by the way?

Ignorant.

Ignorant, yeah.

So I went through the, I'm so sorry, and I didn't mean to.

And please forgive me, Sarah, and your beautiful daughter,

Tiffany.

And we go to commercial, and they come back,

and they said, her name is Sharon.

Ha, ha, ha, ha, ha, ha, ha, ha, ha, ha, ha.

Did you say, yeah, apology for the apology?

Yeah, then we had to do the whole thing again,

which was now, nobody wants to sit

through the nearly tearful apology twice.

Yeah, sure.

So you have the luxury of being a slight tape delay

where you can go back, you can catch something like that.

How do you then?

Have you ever done that?

Which?

I did Conan once, and I was driving,

when he was doing, after the Tonight Show, the Conan show.

And I was driving back, and we had done a bit in the opening.

And I thought, boy, I'm going to spend a lot of time

writing an apology in the right column of the Huffington Post

next week about why this joke, and so I called,

and I just said, can you just take it out?

They did, and it was a great joke.

Did you get requests?

Did you get requests like that from guests that would drop you?

In those days, you would hear about it the next week

from their publicist.

Sure, yeah.

Or when you would try to make the booking again six months

later, you would hear about it from the publicist.

I said this one thing that we had to get cut out,

which we'll cut out of this, too, is, yeah, no.

It was just like a flippin' remark.

They might be recording, and they won't cut it.

So it's nay.

Very good, very good.

Now, what was the joke?

Can you tell the joke?

All right, if you don't tell anyone.

You know, by the way, this was, I'm guessing this was 10 years

ago, too, and it was just a joke that was, again,

I thought a great joke.

By the way, if he gets canceled, Dave,

will you fill in for Will?

Sure.

No, he doesn't own a laptop.

That's the requirement of the gig.

It's just owning a laptop.

What were you doing in London, by the way?

What was, I was writing.

I was doing a rewrite on a script with a film with Chappy.

I don't know if people remember Chappy.

I remember the name from the show.

Yeah, my writing partner, so we were doing it.

Dave, you just missed kind of, I mean, we just touched on it.

You kind of missed that cancel culture just at the end.

Yes, it was happening, but not at the rate

it's happening now, right?

That's all.

Yeah, do you think the writing, no, no.

Do you think that your writing process would be?

Good point.

Careful with the good point.

Slow down.

And then he said, good point.

Do you think your writing process with your staff each night

would have been different in today's culture?

Yes, without question.

Absolutely.

And my personal feeling about this is.

Careful.

And you hear quite a lot of discussion about,

oh, are we too woke?

Are we canceling too quickly?

Are we over-correcting?

And I feel like, let's over-correct and see what happens.

Who the hell cares?

Sure, yeah.

The worst that happens is, oh, we've over-corrected.

And then it'll re-correct.

But there are many, many things a person

needs to be smart and sensitive about that here to for.

Perhaps we were not.

Two of my favorite guests that you had on your show a lot.

One was your first guest and your last guest, Bill Murray.

And the other was, yeah.

And the other one was the incredible,

and I was fortunate to know a tiny bit, Charles Groden.

Can you talk a little bit about those two guys?

Well, Bill Murray put you in business.

He was in Boston last night.

I don't know why you didn't use him.

No.

He's playing golf at Double Beach.

Oh, playing golf.

I'm sorry.

OK, I got some bad info.

We couldn't make Bill's deal last night.

No.

Bill put you in business.

And he did it on our first show at 10.30, I think, or no,

12.30, whenever.

Depending on time zone.

And then he came on the failed morning show.

Bill came on, and Steve Martin came on the failed morning

show also.

And it was people like this that gave us a lifeline.

Because they were so and still are beloved and generous.

And to come on, these two guys and just a miserable little

smoking rag of snot.

Sure.

Yeah.

Was it something like that?

Was I talking about them?

No, no, I'm talking about my show.

You want to be clear?

Not my show.

Oh, got it.

No, it was great.

So in every case, having Bill on the first show was lovely.

Did it make you feel like you're making us feel right now

like a validation beyond your wildest expectations?

We're real happy you're here.

Yeah, I'm happy to be here.

I loved Bill then, and I love Bill now.

And he's never, he was always on the show.

And he was always generous with his friendship

and his talent for me in the show.

Such a brilliantly hilarious guy.

Another guy that, of course, we all.

It's easily hilarious.

That never works hard.

Well, there are certain people, I was

describing that they have no choice in the matter.

Bill has no choice but to be funny.

Will Ferrell, whom we had on our first night in DC.

Yep, there you go.

He has no choice but to be funny.

Marty Short, maybe the funniest person on the planet.

He has no choice in the matter.

He wakes up and that's his disposition.

But I was also going to say, and Jason brought up,

we'd been talking about Charles Groton.

Jason did a film with him.

And he was an incredibly funny guy, an incredibly good actor.

And what I always loved about his appearances on your show

is he came in with a point of view.

So he had a story, which was often

that he was not pleased about being on the show.

Yeah, that's right.

He did not want to be there.

And then somehow, immediately, even you saying,

welcome to the show, he was really put off by that.

Yeah, that's right.

And did that kind of, he set up a parameters of a game

for the two of you.

It was delightful, but that model, that template,

comes from his appearances on the Tonight Show at Johnny Carson.

And he would go on with Carson.

And his point of view with Carson was,

you don't know anything.

You're wealthy.

You don't go anywhere.

You have people do everything for you.

And then he would start with Johnny.

For example, what's a quarter milk cost?

You don't know what a quarter milk cost.

And he would just run Johnny around the theater like that.

And the feeling was that, ooh, there's bad blood.

But no, they both loved it.

And it was the same dynamic that he brought to our show.

That must have been one of those examples of a guest

who, when they came on, they made the show better.

And you were so grateful that he'd been there that night.

That's exactly right.

And you mentioned Marty Short.

Oh my goodness.

This guy.

Marty, Marty.

You're right.

Can't help but be funny.

Can't help.

And I love, because he does it all the time.

It's an old bit, but he'll walk into Sean's house and go,

I can't believe you live here.

I mean, I've seen your work.

I can't believe it.

You know, just true.

That's all he does.

By the way, every time I laugh.

Of course.

Yeah.

Of course.

Brilliant.

When are you?

Canadian.

Yeah, very Canadian.

Yeah.

We seem to have a lot of Canadians here tonight.

Listen, I don't want to take any more of your time.

You're just an incredible guy.

I mean, listen, you know, you've got to.

58 minutes into this, you don't want

to take any more of my time.

I just can't tell you just me personally.

I don't want to speak for these two.

This is a peak in my life and will be hard to be top.

Thank you so much for saying that.

Way too kind.

No, seriously.

I concur.

I think the first time I did your show,

I think it was the first time that my parents really

believed that I was in show business.

Yes.

And it's been an absolute thrill to get to know you.

Everyone, Sean, did I leave you out?

Is something loving to say about me?

No, I do.

And it's a longer reach, but go ahead.

Yes.

No, I.

You should have your own talk show.

OK, well.

By the way.

So, Sean, I want to say you were going to have a talk show.

Who knows what's happening?

So listen.

Well, no, wait a minute.

You can't keep something like that from these guys.

All these guys.

It's available.

They're not going to say anything.

No, I echo what Will said about, and I know you've heard.

I know your reaction whenever there's praise that, you know,

it's always, I get who you are, blah, blah, blah, blah, blah.

You know.

Stop rolling your eyes.

No, but I really want to, because I'm never

going to have this time again to say this to your face.

But I echo what Will said, the first time

you go on late night with David Letterman

was the first time you know you made it.

Because, and then if you did well,

you came back again and again, and you always had me back.

And it was such a, every time it was just like now,

I just can't believe I'm in your presence because I

revere you so much.

Well, you're so kind, but I.

Thank you.

Yeah, yeah, yeah.

But you didn't, you guys weren't guests on the show by accident.

No, I was.

We loved, you weren't actually?

Yeah.

Somebody canceled at the last minute.

I know, it's always going to happen.

I will say there was about five or six years

where I was lucky enough to be doing a couple of talk shows,

and I kept hearing from other, say,

maybe try to get on David.

No, he doesn't, not like kids, or doesn't want kids on.

No, no, didn't say that.

Like I had to.

Wow.

If you're too young, it's like, but so when finally it was the

yes, it was like, oh my God.

When you were old enough to be on the show.

Wait, I'm going to really embarrass you.

Last thing, this is going to embarrass to show you.

You know, you did something.

You did something.

You had, you had a long.

We were ending on such a high note, I took it down,

you're going to take it further.

You were on Alec Baldwin's podcast a long time ago,

and you said during the preview, during the interview,

you said, we just had Sean Hayes who was doing a show called,

I don't know, Hi Ho Promises Across the Street.

And, and you said, you said, God, was he funny?

He's one of the funniest people.

And I saved that clip and it's still on my phone.

Really? Yes.

And so I will say this, now I'm going to admit something.

I moved into still not gay.

No, I, I moved into a new house and I had a bunch,

I had a bunch of photos that were on my laptop and I put them in,

created a file to print some photos, a lot of photos of the kids,

et cetera, to put up outside the boys rooms.

And one of them that I put up to be printed was a photo of,

I guess somebody sent me from your show and I was sitting on the chair

just like that we did at the top where I was, you know, mimicking,

smoking. And the thrill to me was that you,

I was doing this bit and you were laughing.

And it is figures prominently in my hall amongst,

with my family and you.

Yeah. This is, this is a true story.

If my boys were here, they would, they would attest to this

because it was such a monumental moment in my life.

So, so thank you.

And I don't hate to curse you.

There's some pathology behind that.

But how old are your kids?

I have three boys.

I have a 13 year old Archie and I have an 11 year old Abel and I have a

20 month old Denny.

Oh, very nice.

Yeah. Very good for you.

Yeah, thank you.

And you?

All of this, I'm not sure their names, but I think it's fifth.

He's been making Ozark for the last six years.

So, yeah, you know.

We love Ozark.

You know, he's become a very successful, not just actor.

We all love him.

He's become a really successful and incredibly talented director.

Yeah.

And now it's true.

What are we doing?

No, you are a successful.

We're talking about show.

But you need to be talking.

Yeah, you started as a kid on, on, and I give you a lot of shit,

but you started as a kid on, on Little House and the Prairie.

And now you become a really successful and very talented director.

You're a nice man.

You know, what's interesting about this is show business just

is a meat grinder and to begin when you're a child is one thing.

To begin when you're a child and then grow and evolve

into a continuing success in other and every area of show business.

Virtually impossible.

Yes, yes, for sure.

Well, and Sean, you and Opie is about the only.

I'm going to read your Wikipedia page.

Thank you.

Well, it's easy when you have a North Star of incredible.

Like yourself, sir.

Let's please all thank the one and only Dave Letterman.

So nice to see you.

Well, thank you very much.

Thank you.

Thank you very much.

I didn't screw this up for you.

Oh, my God.

Sean, it's always a pleasure, my friend.

Thank you.

Now, I'm going out here.

Take as many cuts as you'd like.

Thank you very much.

Thank you.

Thank you very much.

Thank you.

Thanks again.

It was a lot of fun.

I appreciate that.

Thank you, Jason.

Thank you.

I mean, I mean, so crazy.

You guys got Dave Letterman.

Yeah.

This is I'm going to get a lot.

I'm going to get a lot of shit for this,

but I legitimately just telling him that story

and then him looking at the face as I'm telling that I almost

started to cry.

I saw you.

I saw him start to cry.

Will he's really soft.

Same.

I was like, should I tell him this?

And I'm going to break down.

It's going to be embarrassing.

So, but you know what?

Did you notice what he did on the way out?

No, which was really cool.

He did the same thing that he did on his talk show

where he goes like this and he just goes, hey, thanks

for coming.

Thanks for coming.

I really appreciate it.

Thanks for coming.

I really appreciate it.

I love that.

I don't know about you guys.

I mean, I know you guys as a teenager, as a guy who's

whatever, well, it doesn't matter how old I am.

But growing up in the 80s, the thing to do was on weeknights

was to stay up late enough to watch Late Night with David

before he did the late show on CBS, which was also amazing.

But to do that, and he so much of the things

that I loved about comedy were formed from watching him.

Yeah, for sure.

For sure, all of us.

And just so that you guys know, not that this is about us,

because it's about all of us, but just so that you guys know.

Since when is it not about us?

This was an enormous thing for us.

Like the fact that he said yes, I mean, he said yes to do this.

He said yes to do this because people listen to it.

That's you guys.

So thank you for doing this for us.

And how would he sign off at the end of the night?

No, Sean, no.

What I just asked.

Give us a second.

Let it breathe.

I'm just saying, I can't remember how he would.

Just knowing that he's still out there speeding

along all those highways.

And bye!

Bye!

Bye!

Bye!

Thank you.

Thank you, guys.

Thank you, guys, so much.

Thank you, guys.

Bye!

Bye!

Bye!

Bye!

Bye!

Bye!

Bye!

Bye!

Bye!

Bye!

Bye!

Bye!

Bye!

Smart loss.

Machine-generated transcript that may contain inaccuracies.