Conan O’Brien on Hosting the Oscars Again & the Letterman Bit That Would Have Ended His Career

Our first guest tonight is the tallest and pinkst man ever entrusted to host the Academy Awards. He returns to the Oscars live Sunday night, 7 Eastern, 4

Pacific, right here on ABC and on Hulu 2. Please welcome Conan O'Brien.

2. Please welcome Conan O'Brien.

What's that? Hey, how are you? I'M GOOD.

HOW ARE YOU? I'M GOOD. I'm not asking like a how are you? How are you? I'm

like that's great. Thank you. Thank you.

Thank you.

>> Okay, that's great. You sound like an angry jury, so just settle down. That's

more alarming than fun, but I appreciate it.

>> I should probably not point out, but um this is my show and none of them chanted my name when I came when I walked out here. There's a lot of anger in that

here. There's a lot of anger in that chair already. Yeah. I owe them all

chair already. Yeah. I owe them all money. Yeah.

money. Yeah.

>> You're hosting the Oscars in like three and a half days, I guess.

>> Yeah. Yeah.

>> Not even four days.

>> You've been there and uh there are many challenges. Uh today was a very long

challenges. Uh today was a very long day. Uh and yes, today was a very long

day. Uh and yes, today was a very long day of all media. You do a lot of press, >> right?

>> Uh and you tell each city in America that you're my favorite city.

>> Uhhuh.

>> Oh, you did that thing.

>> And then the Yeah. And then the the station in Banganger, Maine, said that you just cheated on them with Cincinnati and uh it all gets very nasty. But um

but I've been working on this for a while and I've been out workshopping jokes in different clubs.

>> Yeah, I think it's interesting that you do that. I was always too paranoid to go

do that. I was always too paranoid to go and read the jokes to an audience in a club because I worried that somebody would give it to TMZ or something. But

it seems like people and I'm really heartened by this idea that the one thing that people will still protect is punchlines to jokes and the endings to movies and TV shows, right?

>> Yeah. I also think if the jokes aren't great, they don't repeat them, you know, and that's my secret.

>> How do you decide where you're going to go to test the jokes? Uh, you know, I have a terrific writer, uh, who worked with me for years and worked with me on the Oscars last year and this year and also works for you, Lorie Kil Martin.

>> Yes. Yes.

>> And Lorie Kil Martin is >> great.

>> And Lori Kil Martin is like my coach and she's a terrific standup in addition to being an amazing writer. And she will say, "All right, Conan, tonight you're going to, you know, the Chatterbox in

Coina." And the next thing you know, I'm

Coina." And the next thing you know, I'm I'm changing passports. I'm I I mean I'm driving for a really long time, but I go to these places and I love it there. A

lot of young comics and they all hang out in an alley before the show and there's just a great vibe. Uh it's

really fun to get out there >> and they're probably very excited that you're there, right? I mean, the audience >> it's nice. They are they're they get over the shock of seeing what I look like in person and then >> and then once they recover from that, we

uh we have a really good time hanging out. And what's lovely is you go to

out. And what's lovely is you go to these different places. I mean, I've played places where you have to hold the joke because you can hear that bowling is going on uh and behind a wall like

you go to these different joints and I love showing up where no one uh expects me to be there. They don't particularly want me to be there and it's really fun just to pop up and >> and have they like the stuff? Has it

been >> They have um they also uh there are times where there are certain areas we cannot crack. One of them is uh the

cannot crack. One of them is uh the movie Train Dreams. Yeah, right. Can't

get a good joke for Train Dreams, which maybe means there is no good joke for train Dreams. And let me ask this audience, who has seen Train Dreams?

>> Go live. Okay, let's do it again.

>> That's eight people. No,

>> one of the issues. And so I think my writers, they write a lot of jokes and I keep going out and trying them out. I

think they've written 5,000 jokes dreams. >> Not one of them is any good.

And these are very good writers. So I

blame Train Dreams. I think it's the movie. It's a movie about a lumberjack.

movie. It's a movie about a lumberjack.

It's a lot more serious than that. Like

if you have seen the movie, it's probably worse, right?

>> It's very it's a tough I mean, first of all, it's a beautiful movie. I don't

mean to underline the movie. Uh it's a beautiful movie, but it's just no joke sticks to it. So I might move on and not skip Train Dreams. Who's going to care?

>> Will you sing this year? Will you sing or >> I can't reveal what I'll do. Um but they saw a huge ratings drop when I sang last year. I mean just a hole that dropped

year. I mean just a hole that dropped off the earth. People threw away their flat screen televisions. But um last year did anything go wrong? Something

that you you expected it to go one way and it did not go that way, >> you know? No. And I don't know if I mean you might be the same way but my philosophy is prepare prepare prepare

and then I kind of want something to go sideways%. Yeah.

sideways%. Yeah.

>> Uh it's it's exhilarating. Yes.

>> And people in the audience and at home see that something has gone wrong. Now

there's good gone wrong and then there's bad gone wrong. Right.

>> I don't want bad gone wrong. I want good gone wrong. And so you just have to see

gone wrong. And so you just have to see if that's going to happen or not.

>> When that happens, I think it's one of the few times that the audience knows that what you're saying is truly spontaneous >> in the moment. Yeah. They know that this wasn't written. It wasn't scripted. Uh

wasn't written. It wasn't scripted. Uh

that old woman just fell.

>> And so I am spreading oil, olive oil, all over the floor.

>> That's good.

>> Here comes Dame Judy Dench. You know,

>> I'll do what it takes to get a good show. How locked in are you on the

show. How locked in are you on the monologue? Is it set

monologue? Is it set >> it? You Here's the interesting thing

>> it? You Here's the interesting thing about the these monologues is that we started working on this thing, you know, early January, late December, and people will write jokes that are really like,

oh, this is a great joke. And then you realize it's 35 news cycles ago now, >> right?

>> So, you'll be like, can you believe what's going on with Venezuela? That's

insane.

And you know, there was a maybe a couple of months ago that was like, that's great. I mean, trust me, there'd be a

great. I mean, trust me, there'd be a joke in there. I wouldn't just go, "Isn't that nuts?"

Be great if my whole monologue was naming the movie.

I should have Murray Supreme. Isn't that

cuckoo?

>> I kind of There's actually a part of me wants to do that, Oscars.

>> And why why are you imitating Dennis Miller when you do that? Is that

intentional? Not me more.

>> But but anyway, uh yeah, it was so uh you you'll write something and you see jokes come and go because we live in fast times. There's a lot happening,

fast times. There's a lot happening, >> a lot of other award shows.

>> There's a lot of other award shows.

There are other invasions. There's all

these new stuff happening all the time and you need to keep up with it. So

things can happen week to week, day to day. So you have to leave room for that,

day. So you have to leave room for that, I think. Do you have jokes that you've

I think. Do you have jokes that you've decided you will not do that you would that you could share with us?

>> No. Okay. Uh

>> cuz they're bad. Uh uh the one I have is Train Dreams. It's a train Dreams joke.

>> Oh, do it please.

>> Do you want it? Okay. This audience has Yeah.

>> Oh, YOU HELD IT. NO. OH, GREAT. TRUST

ME.

>> This is the best train D dreams joke out of 5,000.

Train Dreams was nominated for best picture. Finally, a movie that proves

picture. Finally, a movie that proves being a Pacific Northwest lumberjack in the early 1900s wasn't as fun as it sounds.

NO NO NO NO.

PITY applause doesn't work.

>> You waited. You were sad as I was.

That's why you're not going to see this.

>> Yeah. All right. This is for you. Yeah,

that's Thank you. I appreciate you can use that tomorrow. Yeah.

>> Hey, can I mention that I thought >> Come out tomorrow night and paste that together.

>> I will do that joke tomorrow. By the

way, nobody will even realize we've done it here tonight. It'll be completely news for today.

>> You I think you did a great job in the movie you were in. If I had legs, I could kick you. I really was impressed.

>> Thanks.

>> I mean, I was and I was hoping and I feel like in a way you were slighted because your co-star Rose Burn with whom you share a lot of scenes. Yeah.

>> Is nominated for one of the big ones, best actress.

>> Yes, she's up for best actress. And one

could say that I elevated her performance.

>> One could say it, but one wouldn't cuz you'd be insane.

>> I disagree.

>> I I No, I I It's interesting. People

that have seen it are like, "Oh, I think I thought Conan was going to do his Conan thing and I did not."

>> You play a psychiatrist and it seems Yeah. kind of a also, right?

Yeah. kind of a also, right?

>> That part was real.

the uh >> let the old inner out. That sounds bad.

>> The guys they nominated in the guys that were nominated uh instead of you, Benio Del Toro. Ah,

Del Toro. Ah, >> Jacob Allorti. Ah,

>> ugly.

>> Ugly. An ugly. Just an ugly man.

>> Delroy Lindo.

>> I mean, whatever.

>> Sean Penn.

>> That guy can't act his way out of a bag.

>> Stellan Scarsgard.

>> That's not even a name. You're someone

opened a can of alphabet soup and threw it on the wall.

>> YOU'RE BETTER THAN ALL OF THESE GUYS.

>> I'M BETTER THAN ALL OF THEM COMBINED.

AND YET I WAS DENIED. DENIED.

>> That's the actor you want to see.

>> But I heard you're in uh you're in Toy Story 5, which >> I'm in Toy Story 5.

>> That's pretty great.

>> Yeah.

>> Who do you play in Toy Story 5?

>> What do I play?

>> Yeah. Oh, what? I'm glad you asked. So,

they come and they pitch me, Conan, we want you to be in Toy Story 5. We think

it's just an amazing uh part of the franchise. It's an amazing script and

franchise. It's an amazing script and we've got all the people are coming back for it. You know, everyone's coming

for it. You know, everyone's coming back. Tom's coming back. Tim's coming

back. Tom's coming back. Tim's coming

back. It's just amazing. And we have a role that we think is definitely you.

And I said, "Well, this sounds great.

Who is this sexy guy?" And um they said, "You're a a toy, an electronic toy that teaches two-year-olds how to go potty."

>> This is This is an existing toy.

>> Yeah, there are toys that help kids that are like, "Good for you." You know, you >> Is that that the voice you're going to use?

>> Uh you'll have to wait and see.

>> Good for you.

>> But um anyway, that's my that's what I am. And I was I said this is the

am. And I was I said this is the universe once again telling me exactly who I am. Conan O'Brien is here. He's

the host of the Oscars on Sunday. We'll

be right back. We are back with Conan O'Brien. Uh you now you hosted a late

O'Brien. Uh you now you hosted a late night show at one time.

>> Yes, I did.

>> For 28 years. Correct me if I have it wrong. Yeah.

wrong. Yeah.

>> Do you like being a guest on a talk show? Uh, I I really love being a guest

show? Uh, I I really love being a guest because I really love being a guest because when you're the host, you need to worry about how do I get this, you

know, into the conversation. I got to get to this question. We're running, you know, tight on time. I got to get him out of this story. When you're the guest, you don't care.

It's your problem. You know, I could start I could tell a 45minute story right now.

>> Please go ahead. And well, funny you mention it.

>> We'll do a two-parter tomorrow.

>> Grandfather. No. And then um it's it's just kind of nice to go out and and be on this side. It really is. It's a

change of pace. And

>> for me, it's fun to talk to you about the things that nobody thinks about. The

weird little things like how do you greet the person that comes out? If

they're from Europe, you have to kiss them on each side of the face. If

>> I never let a European on my show.

>> Oh, really?

that very reason I thought I didn't know that >> and I made that very It said there was a sign outside that said no Europeans. Uh

>> what about doing Letterman? Was that

scary for you? Because for me that was the scariest thing I ever did.

>> Well, you know our generation that was our guy and we were like, "Oh my god, it's Dave." And then he I was going to

it's Dave." And then he I was going to be on his show and this is early days of my late night show. This would be back in 1993 and my show was hanging on by a thread. People said, "Who is this guy?

thread. People said, "Who is this guy?

What kind of name is that? His hair

looks stupid. It looks like a dessert."

Uh, and people were really down on me and I thought, "I'm going to go away."

And then I got invited to go on Dave's show and it was over at at CBS. So, I

went over there. I was going to go over there and and this is a big chance for me to maybe save my show. And um I remember at the time the we were sitting around with the writers

>> and what I love to do is pitch an idea that is intentionally bad that I would never do but it just makes the writers laugh, >> right?

>> So I said, "What if I come out and you're Dave and I sit down next to him and he says, "Well, you know, this young man took over our show and he's over there at NBC and it's good to have you here and now Conan tell me what's going on over there. How's the show going?"

And I said, "Well, Dave, I just think that maybe And freeze >> for how long?

>> Freeze and hold it. How long? Freeze and

hold it for a really long time >> and never break. So just like, yeah, Dave, I just think and while I do that, he's waiting for a bit and then the audience kind of is like, "Huh?" And then there everyone's

like, "Huh?" And then there everyone's weirded out and then he starts talking to Paul and then Paul's like, "Yeah, I don't know." Oh, and he's like, "Yeah,

don't know." Oh, and he's like, "Yeah, well anyway, so Conan," and I hang on it. And so it was just making all of us laugh as one of those stupid, of course, I'll never do this.

And my head writer at the time, brilliant genius, Robert Smiggel, said, "You have to do it. YOU HAVE TO DO IT.

DO IT. IT'LL BLOW PEOPLE'S MINDS." AND

OVERNIGHT, PEOPLE WILL SAY, "THIS GUY'S A GENIUS." And I said, "I will be off

A GENIUS." And I said, "I will be off the air immediately. I will never be invited back." I mean, literally hold it

invited back." I mean, literally hold it to the point where they carry me out of Dave's show.

>> Well, now I hold it the whole time.

>> Now you're selling it again.

>> No. And like literally hold it and it's, you know, the New York Post Conan has meltdown. I mean, everybody just what

meltdown. I mean, everybody just what the hell happened? And it's one of those things that Yeah. I get fired, but like 15 years later, comics, you know, saying

like the time Conan did that, that was, man, he just, man, he showed the man.

And um >> and meanwhile, you know, I'm I'm in an alley somewhere with no pants on >> and Dave hates you. Yeah. Just what you want.

>> And Letterman hates me as being the guy that tanked his show that night. So, um

but that's the kind of thing where I had people around me, sensible people saying, "You got to do it, man."

>> I know, Robert. I don't think sensible is a word.

Robert, we love you, but you're insane.

>> Yes, that's correct.

>> Tried to kill my career.

>> Um, you're Irish, right?

>> I'm afraid I am.

>> Yes.

>> You I I think I told you this uh off camera, but that doesn't count. Um,

>> you said a lot of things off camera.

>> That's right. Yeah.

>> We my I took my family to Ireland for my dad's 80th birthday. We went and every place we went and we traveled all across the country. Every place I went, they're

the country. Every place I went, they're like, "Conan was here. you somehow hit like every like what the Smurfs are to

Belgium, Conan is to Ireland is everywhere you go. I am 100% Irish meaning uh I took a genetic test and it said you are 100.0000

and the guy who took the test said we don't see this very often and he said it's actually not good.

>> It's inbreeding. You're inbred. Thank

you for saying what no one else could say.

A lot of people living in a hut together. Uh

together. Uh so um yeah, this is what happens. Uh

and so I um I I went back and we had a lot of we did a lot of fun uh jokey things. And then uh I was going to go

things. And then uh I was going to go and see a great genealogologist said, "I found where your greatgrandfather's home was that he lived in." the home is

gone, but I found a little little spot that he lived on and um it's near the Galbully Mountains and he said, "Let's I'll go there and show it to you." And I said, "We'll do it on camera." And I was

expecting we had these jokes loaded up.

We had props, funny things we were going to do. I was going to try out some Train

to do. I was going to try out some Train Dreams material. And um

Dreams material. And um >> I got a joke right here.

>> See if I Yeah. See if I try it out on a cow. Uh, but I got there and I did not

cow. Uh, but I got there and I did not expect this because I'm not someone that wears my emotions on my sleeves, but I I got emotional. It's very powerful. I

got emotional. It's very powerful. I

felt the same way >> when you're standing there when you saw my great-grandfather's place.

>> Yes, I did.

>> I said, "Well, this is a guy who is first of all more than 100% Irish."

>> He was 140% Irish. And can I tell you something? We got shovels and he's a

something? We got shovels and he's a terrific guy.

No, I I went to I did the same thing I had, but it was there was some of the house still there.

>> Yeah.

>> So, I think maybe I don't know my >> to me it was just seeing uh that this was a very small plot of land. He was a tenant farmer so wasn't his. They didn't

have money and uh he needed to uh move on because it wasn't working and probably not enough to eat, couldn't sustain. So he left and went to America

sustain. So he left and went to America and you know there here I am a couple generations later. And what's amazing to

generations later. And what's amazing to me is you have that experience and you stand there I have incredible empathy for people who have immigrated to

another country. Yeah. Because it takes

another country. Yeah. Because it takes it's incred. It takes

it's incred. It takes it takes an entire lifetime to go to a country where um you know often it's people who are coming to a country where

they don't speak the language and they have to spend their entire lives just getting things started for the next generation and it's a whole lifetime that you're that you're feeding into

this process. So, I was just thinking

this process. So, I was just thinking about this guy who I'll never meet uh was had to do that. And I think I think I was overcome by that. I was overcome

by the fact that there's a lot of sadness in that story and in a lot of these stories. People leave not because,

these stories. People leave not because, hey, I just want to go have fun in America. They leave because they have

America. They leave because they have to.

>> So, it was it was really it was >> I mean that's that is a beautiful story.

I hope you don't tell at the Oscars.

It's depressing and nobody's going to like it. They

like it. They >> What I'm going to do is open with that.

>> Uh-huh. Yeah. Yeah. And then

>> talk about the struggle of immigrants.

Then train dreams. Bang. Train dreams.

Bang. Five in a row. Each one worse than the other one. And then I'm going to show Train Dreams in its entirety.

>> Smiggle thinks it's a good idea.

>> Smiggle says you. And then I'm going to go like this. I HOPE YOU HAD A GOOD TIME.

>> O'BRIEN. EVERYBODY, YOU CAN'T MOVE.

WATCH THE OSCARS LIVE SUNDAY NIGHT, 7 Eastern, 4 Pacific here on ABC. We'll be

back with the vacuum pump.