
Filmmaker Judd Apatow feels very needy about being Conan O’Brien’s friend. Judd sits down with Conan to discuss his new visual memoir Comedy Nerd: A Lifelong Obsession in Stories and Pictures, how auditioning for Jim Henson turned him away from stand-up, the books that educated his younger self on life, divorce, and how babies are made, and more. Plus, Conan follows up with his lawyer David Melmed for an example of a call to secure the rights to a popular song. For Conan videos, tour dates and more visit TeamCoco.com. Got a question for Conan? Call our voicemail: (669) 587-2847.
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Conan O'Brien
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Sonam Obsessive
Cruise, baby.
Conan O'Brien
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Judd Apatow
Hi, my name is Judd Apatow and I feel very needy about being Conan o' Brien's friend. Folly's here. Hear the yell back to school, ring.
Conan O'Brien
The bell, brand new shoes, walking loose.
Judd Apatow
Climb the fence, books and pens.
Conan O'Brien
I can tell that we are gonna be friends? You can tell that we are going to be friends. Hey, Conan o' Brien here, listening to the highly unedited just off the cuff, Conan o' Brien needs a friend. We never stop and start again.
Matt Gourley
This is definitely not a restart.
Sonam Obsessive
No.
Conan O'Brien
Conan, how are you? You doing good?
Sonam Obsessive
I'm great.
Matt Gourley
And get it right or we're going to have to do it over again.
Sonam Obsessive
I am doing great, thank you.
Conan O'Brien
And how are you, Matt Gorley?
Matt Gourley
I'm good, thanks.
Conan O'Brien
Hey, what's on your mind?
Matt Gourley
Something off the cuff? We haven't talked about this.
Conan O'Brien
I was going to get you there. You don't have to cut me off and say, hey, I've got something. I was going to get you there with. Hey, what's on your mind?
Matt Gourley
On a recent episode, we talked about having a listener in high school that was listening during high school. And then Adam had mentioned that he knew someone that was in seventh grade. Giles that listened but we now have beat that record. A friend of mine, Jeremy Connor, has a son named George, who loves the show, started when he was 8, is 9 years old now and listens to the show and would love an autograph. Would you mind signing this poster?
Conan O'Brien
I'm not signing that.
Matt Gourley
You don't have to.
Conan O'Brien
No, I want some scratch. I want my payday. This is so incredible. He's.
Matt Gourley
He's nine, but he listened, started the song.
Conan O'Brien
Oh, well, nine, that's when the real cynicism kicks in.
Matt Gourley
But this is for you, George. Thanks for listening.
Conan O'Brien
Um, yeah, of course. This is so nice. I love that I'm doing this. It's nothing more exciting to listen to a guy sign something scribbly. Um, you can watch it on YouTube. Yeah. Okay. Squeak, squeak, squeak.
Sonam Obsessive
It's also very fascinating to watch someone sign a poster and to hear someone.
Matt Gourley
Comment on someone signing a poster.
Conan O'Brien
Well, there we go. Yeah, that was good use of our time. Listen, I don't understand how a 9 year old. What would they connect to?
Matt Gourley
We don't have any listeners over 14.
Conan O'Brien
That's not true. Okay. That's not true. I can beat all of this. There's a woman who is seven months pregnant and her child's been listening in utero to the podcast and hates it. Loathes it.
Sonam Obsessive
Kicks a lot.
Conan O'Brien
Yeah.
Sonam Obsessive
Yeah. Kicks a lot when you're listening.
Conan O'Brien
I'm just trying to imagine. Maybe it's.
Matt Gourley
They can tell that my friend Jeremy was saying that when this podcast gets edgy, it still has a kind of innocence at its heart. And he felt that that was okay for the child.
Conan O'Brien
I think maybe that's it.
Matt Gourley
But that might have been negated by the recent Deez Nuts Milk Dem Titties episode.
Sonam Obsessive
We did do a lot of. You know what.
Conan O'Brien
Yeah. But you can appreciate that on two levels. Yeah. I used to watch the original Batman series with Adam west and just appreciate it. On the crime fighting, when they were making jokes about politics, I didn't pick up on any of it. I just loved. And then years later, I got all the great dry humor and great references. I picked up on that much later. I think that's how people listen to our podcast. You can listen to it on this very friendly crime fighting level. And then there's all the nuances that we pack in here.
Matt Gourley
What you're saying is people should do a re. Listen to find the onion layers.
Conan O'Brien
Yes. And they should listen to all the new ads that we place in there.
Matt Gourley
Oh, I see.
Conan O'Brien
Because there's dynamic ad insertion talk on that.
Sonam Obsessive
Yeah.
Matt Gourley
A little bit more about that process.
Conan O'Brien
This is an idea I had a lot of people think. I don't really know how podcasts work, but my idea a while ago was, hey, we should have dynamic ad insertion.
Matt Gourley
What is that exactly?
Conan O'Brien
Well, it's. When you have dynamic insertion of aforementioned ad.
Matt Gourley
If you could expand on that a little bit.
Conan O'Brien
Well, sometimes there's something that doesn't have an ad in it, and if it does have an ad, it's kind of flaccid and not moving. So I think, well, it should be moving or dynamic and it should be inserted. So it's inside.
Matt Gourley
And that's how you explain this to the people that put it into process.
Conan O'Brien
I did. I called up some audio whizzes. Adam, jump in here for a second. Aren't I correct?
Sonam Obsessive
No, no, don't jump in here. I'd like to hear you keep going.
Conan O'Brien
X. Why do you.
Judd Apatow
I'm actually reeling from the fact that you said dynamic ad insertion just off the top of your head. I'm.
Conan O'Brien
When you put the SiriusXM chip into my head, that was one of the words that was readily available. It's a dynamic ad insertion, right? Yes, covered that. Listen, if you can't handle what I'm saying or you can't understand it, don't attack me. I'm telling you in a very authoritative way that I had an idea about two and a half years ago that ads could be inserted dynamically.
Matt Gourley
Close to 10 years, probably.
Conan O'Brien
No, not the way that we're doing it. My idea was that it could be. What's a good word for constantly changing, always in motion dynamic, and that it could be put into something which would be, I don't know, inserted, and that you could use it on an ad. I started that idea. Remember this?
Judd Apatow
Like it was yesterday.
Conan O'Brien
I called you in and I said, I've got three words to say to you. Dynamic ad insertion. You freaked out and then you left the room. And then the next thing you know, we were doing dynamic ad insertion.
Judd Apatow
We were the first to do it.
Matt Gourley
I do apologize, because you've clearly demonstrated your knowledge on this subject.
Conan O'Brien
It is a way that people can have their ads dynamically inserted. And it is one of the reasons that I think. I mean, this podcast used to make about. I think it was $300 a year.
Judd Apatow
Yeah.
Conan O'Brien
But after dynamic ad insertion, we now make more than the gross national product of many countries throughout the world, including Switzerland and countries that border Switzerland.
Judd Apatow
Yeah, I still just. I can't believe that you even know that you even think about Dynamic ad insertion. And you actually understand how it works.
Conan O'Brien
For you to say.
Judd Apatow
I've never seen Adam so excited.
Conan O'Brien
I know he's really happy.
Judd Apatow
I am.
Conan O'Brien
I remember the day I came in and I said, if we're using microphones, I want them to be shure microphones. Remember that?
Matt Gourley
Just. Just take some time.
Sonam Obsessive
Just checked it.
Conan O'Brien
What are you talking about?
Sonam Obsessive
Also, it's here too. Yeah, yeah, yeah, you said that. I remember you saying that.
Conan O'Brien
I wanted that.
Judd Apatow
What was the model though?
Sonam Obsessive
Yeah, sure.
Judd Apatow
What you recommended.
Conan O'Brien
What's interesting, what I wanted was I wanted it to be in this shape. Remember that? And I drew the shape for you.
Matt Gourley
And did these mics need a preamp or no?
Conan O'Brien
Well, I said as long as it's an SM7B or 8. I don't have my glasses on.
David Melmed
It's a B.
Conan O'Brien
What's that?
David Melmed
That's a B.
Conan O'Brien
Well, I said B or 8 because the eights are fine, but you really want the B. And so once I knew that we had the sure. And that it was an 8 and not a B, I was like, we are ready to go. And we should have dynamic ad insertion. And what I've done is I've created many platforms and these are trilingual, quadrilingual, quadrilateral. We have achieved a new level. These are actually dynamic microphones as well. So dynamic. And I've had this mic inserted. My point. And you know what? We just lost our eight year old viewer. Parents took the.
Sonam Obsessive
Oh, you think we just lost them now? Yeah, I think they tuned out a minute ago.
Conan O'Brien
I don't think so.
Sonam Obsessive
When you said dynamic ad insertion.
Conan O'Brien
No. If his kids had a lot of chocolate milk, he's revan.
Sonam Obsessive
You were kind of sexualizing it too, a little bit.
Conan O'Brien
Well, that's the thing. I was kind of.
Matt Gourley
Apologize, George. I apologize. Jeremy Giles.
Conan O'Brien
I don't think children should be listening to this.
Sonam Obsessive
I don't know.
Matt Gourley
I don't think anybody should be listening to this.
Conan O'Brien
You know what? We finally agree on something.
Sonam Obsessive
Yeah. I watched Pulp Fiction when I was 12 in the theaters with my parents.
Matt Gourley
I watched the movie 10 when I was about 6 or 7.
Sonam Obsessive
What?
Matt Gourley
Yeah, I know.
Conan O'Brien
Can you believe that?
Sonam Obsessive
Oh, yeah.
Matt Gourley
No, I learned a lot.
Conan O'Brien
Oh, my God.
Matt Gourley
Oh, Bo Derek running on the beach.
Conan O'Brien
Pure cinema. Remember the movie Nine and a half Weeks?
Matt Gourley
Do I remember it?
Conan O'Brien
I watched that when I was 47 years old. Still a little early for. No, I didn't know what was happening. Why are they lying together? What's happening? And my wife was like, you know, she was Busy with the kids. And she was like, no, they're. Let me explain. Why are they in bed? Moving.
Matt Gourley
Why is their nap so wet?
Conan O'Brien
What did you do that for? You always go too far. I don't think I do. Do you know anything about going towards the line? You just jump right over.
Sonam Obsessive
Yeah, that's not cool.
Matt Gourley
I call them.
Sonam Obsessive
Like I said, you know, this is a clean podcast, sir. Yeah.
Conan O'Brien
You just started this whole thing by talking about how there's a two year old listening show.
Matt Gourley
I love any. Any incendiary words. Nap and wet. They're not inherently dirty.
Conan O'Brien
You're an awful person. Anyway, let's get into it. My guest today is not an awful person. Good transition. The director, producer, and screenwriter behind such movies as Knocked Up, Superbad, and the 40 year old Virgin. He now has a new visual memoir. It's very dynamic, I'm told. Titled Comedy Nerd. A lifelong obsession in stories and pictures. I'm excited he's here today. Judd Apatow. Welcome. You know, this is interesting because you've just flooded my voicemail with just demanding that you come on the show, which came across as very needy.
Matt Gourley
Who's gonna be the neediest? This is like a real battle of wills.
Conan O'Brien
This is two guys facing each other in high noon.
Judd Apatow
I'm the only guy who begs to get on podcast. Like, I. I'm just checking the boxes because it is a way to find out if someone's your friend. Like, recently, you know, I gotta plug my book Comedy Nerd. So I. I asked someone if I could be on their podcast, and they said no. And I was like, whoa. They must have checked.
David Melmed
Who was it?
Conan O'Brien
You gotta tell me. Didn't hear it.
Matt Gourley
Hyson Heisenson. Heisen.
Conan O'Brien
Hyanson has the number one podcast in the business.
Matt Gourley
I just got on his podcast. You must have got.
Conan O'Brien
He's since kicked you off. They're not airing it. Hyansen. Well, I think that person showed great tact. And. No. What?
Matt Gourley
I think oversight.
Conan O'Brien
Oh, you're right. You're right. It should be something that is good for Judd.
Judd Apatow
But this is a business. I need to realize this is a business. And, you know, for some people, you know, they got numbers. They gotta maintain.
Conan O'Brien
Oh, not us. You know, that is not us. That guy was like, we need asses in seats. You know, we need sex appeal. And I'm like, no, I'm the sex appeal. Oh, wait, Q. Cricket noise. You have cricket noise come in right here. Here we go. No, you source it. Oh, wow. You could source it.
Matt Gourley
No, I don't Want to do the work?
Judd Apatow
You got the cute new haircut.
Conan O'Brien
You know what's so funny? You're the second person today. I came in and people went, great haircut. No, I was flying. Got home, I took a shower, I went to sleep and then put a baseball cap in the morning, and it just flattened out my hair. I've had no haircut.
Matt Gourley
You literally woke up like this.
Conan O'Brien
I woke up like this and stumbled in.
Judd Apatow
What if it's better than the way you've done your hair your entire life?
Conan O'Brien
It is nice. It is nice.
Sonam Obsessive
It does look really nice.
Conan O'Brien
You know what I should do this way? Yeah, yeah. No, it's. This is me just being me, man. It's just that kind of.
Matt Gourley
Now you're ruined it.
Judd Apatow
Well, I've been editing Conan because he's in a few documentaries that you're making.
Conan O'Brien
Nine documentaries.
Judd Apatow
I'm making all of them sometimes.
Conan O'Brien
Do you ever get confused and it's a documentary about Steve Martin, and you have me talking about John Candy, and it doesn't even matter anymore.
Judd Apatow
The funniest one that you're in is the Elvis Comeback Special documentary because you are on not as Conan Funny man, you're on as Elvis Expert. Yes. There is no irony. No one mocks the idea that it's you. And you seem to know more than anyone I've ever seen about Elvis, which is something I thought you just like Lincoln or something.
Conan O'Brien
I have to tell you this. They shot that a long time ago or a while ago. And I forget things. And so I. This is a real story. I'm at home. I love all things Elvis. I see that. There's this thing about the 68 comeback special. I'm like, oh, I'll watch this. Or I'm watching it in my room, in the TV room. I'm watching it, and all of a sudden I heard a very familiar voice say, you have to remember where Elvis was in his career in 1968. And I'm like, what the. And I'm in the documentary talking about. And I. A lot, and I didn't remember that I had done this. And then next thing I know, I'm nodding, going, he's right.
Judd Apatow
I like this guy.
Conan O'Brien
Yeah, I do him. Oh, God.
Judd Apatow
And how do they even know you're the Elvis guy?
Conan O'Brien
I think it's out there a little bit.
Judd Apatow
It is. I've been following you my whole life.
Conan O'Brien
I've never known that.
Judd Apatow
It was, like, enough to go, doc.
Conan O'Brien
No, no. It's Elvis and Son of Sam. I'm in seven. Son of Sam. Docs, we're not here to about Son of Sam. We're getting to him in the second half. We are here to talk about you, Judd Apatow, and you have a book, Comedy Nerd, which is extremely impressive. I got this book, and I'm looking at it, and one of the things that immediately drew me to this book is it's gorgeous photos. It's all photos. I can flip through it. I don't have to read as much as I. And then, of course, it's interspersed with great observations. But it's basically your career, and you've had a career that merits a book of this size. Cause you've made so many great films and you've been involved in so much television and just comedy in general. And if you're a comedy nerd, this is the book to get. I really loved it.
Judd Apatow
Oh, thanks. Yeah, it's. Cause I've always been a hoarder. I found a picture of my room from when I was in sixth grade. And in my closet, you could see I have my Phil Collins autographed album and my Dave Kingman New York Mets autographed bat. I'm like. It's like the Smithsonian in my head. And so when we were doing the book, I, you know, I had. I just scanned everything, and then I got all the photos from all the movies and then wrote some essays after the fact. But I also finished it and thought it's so long that it feels like a textbook about workaholism. Like, this is someone who needed mental help and should have found a better way to get help sooner.
Conan O'Brien
Well, that's why I think it's good at the end. You have a. If you need help, like me, and then which medications you've tried, which clearly aren't working.
Judd Apatow
Are you nostalgic as a person? Like, do you look back all the time at things?
Conan O'Brien
You know, I try not to look back too much because I want to be in it now and making things now. I'm very sentimental. If I just bump into a writer that worked with me in 93 or 94 or an intern, I'm very sentimental for. Oh, my God, you were there. That was so weird, you know, What a special time that was. What a weird, raw, scary time that was. But I like to connect with people from that. From that era.
Judd Apatow
It's weird being older.
Sonam Obsessive
Is it?
Judd Apatow
Isn't it weird?
Matt Gourley
Oh, take it easy.
Sonam Obsessive
What? No, I mean, like, I like getting older.
Conan O'Brien
I was just talking to a friend. We're not talking about you and Matt. We're Talking about older.
Judd Apatow
Older.
Sonam Obsessive
No, no, no, no, no.
Conan O'Brien
Judd and I fought in the Korean War. He saved my life.
Judd Apatow
Memories. Conan from the 80s, you know, like, you have stories about, like, Sandler from 40 years ago.
Conan O'Brien
Well, here's the weird thing. Has it been 25 years since 40 year old virgin or 20 years? 20 years. Okay. I remember when I was in college and I was working on the humor magazine, and grads, old grads would come back and I'd be like, oh, my God, these fossils. And I would say that to their faces. I would say, the Natural History Museum is down the block.
Sonam Obsessive
But what the fuck?
Conan O'Brien
I've done the math. And I realized that if I showed up now, it would be the equivalent of someone showing up when I was in college who had been drafted in 1941. I mean, it's like the same for real. And I can't. I cannot accept that.
Judd Apatow
No, just by being older, you're creepy. You know, like if I just go into a dance club and do nothing but stand there.
Conan O'Brien
Yes.
Judd Apatow
People will call the police.
Conan O'Brien
You just being on an elevator is creepy. Yeah, you want an escalator creepy. That is the best. That is the. That is such a great observation that you don't have to do. It's not, oh, he's hitting on a 20 year old. No, he's standing there.
Matt Gourley
It's the less you do that's creepy.
Conan O'Brien
And he's drinking a glass of water and it's creepy.
Judd Apatow
Yeah, it's like in New York, there's a park, like, for kids. And there's all these kids, like, little, you know, rides and stuff on it. And there's a big sign that says, you're not allowed in the park without a kid. So if I just walk in there, I'm a creepy person? I'm not allowed to enjoy the joy of children.
Conan O'Brien
A creep walking around with a ventriloquist dummy. Get the. Get out of here.
Judd Apatow
But it is weird having memories that are from, like, decades ago. And just like, knowing people from, like, their very beginnings to all the things they accomplished, it blows your mind. Like the Mark Twain thing for you. And like with Sandler, when we were all there for Sandler, you just can't believe all this stuff happened, right?
Conan O'Brien
I still refuse to believe that somehow it's been legitimized. You know, it all felt so wrong that we would be allowed to do anything. And now, all these years later, at some of these nice events where you get an award or something, they're acting like, well, what an esteemed body of work. I want to say, no, I shouldn't be here now. This is absurd.
Judd Apatow
It's a masturbating bear.
Conan O'Brien
He was getting the word out on a real problem that I was struggling with.
Judd Apatow
But you. And you got your Mark Twain Award during the Trump administration, which makes it so much sweeter.
Conan O'Brien
Yeah. Yeah, it was.
Judd Apatow
Well, because he could have killed it. It didn't hit his.
Conan O'Brien
I don't think it hit his radar. I think he. He didn't think I was that kind of.
Matt Gourley
He got it under the wire. Speaking of legitimizing, you might get the last legitimate one.
Conan O'Brien
Yeah, well, they might. I don't know what they're gonna do. I don't know what they're gonna do. Yeah, I might be the last comedian ever.
Judd Apatow
It's gonna be Fred Travelina next year.
Conan O'Brien
Oh, I'll be there to support him. Talk about getting older and our influences when we were young. But one of the things that is a touchstone for both of us is Mel Brooks.
Judd Apatow
Like, it's our whole childhood was just that run of high anxiety and all of them. That's why it was fun to make a documentary about Mel. First of all, I got to talk to him for 10 hours. So just to get to ask him questions for 10 hours is amazing. And then it's also. The doc's interesting because it's emotional. Like, he talks about his life and how he feels about it. And it's not just the funny stories. He really goes deep into his friendship and his marriage and his life and his kids. And you see what a great guy he is in a way that I think we see him as a hilarious guy, but he's also this wonderful person.
Conan O'Brien
Do you think something that happens when people get to Mel's age, if they're lucky enough to get to Mel's age, I don't know what he is now.
Judd Apatow
Would he be in his 99?
Conan O'Brien
Jesus Christ. They may be able to access emotions more than they could earlier in their life. And especially with men, some of the walls may become down and they become more accessible at this stage in their existence to really being in touch with stuff that they might not have been able to access when they were 40, 50, 60.
Judd Apatow
Even in the doc, he talks about living through the depression, which is w. When he was a kid. His father died when he was really young. And he just talks about his aunt took a job in a factory to help take care of her sister's kids. And just him talking about what that meant to him because he really had to work in the. What Was it called the shmata business?
Conan O'Brien
Yeah, the garment industry. The garment industry, yeah.
Judd Apatow
And he talks about. It's a miracle that that's not where I landed up. The fact that I had this career and didn't just go into the garment district is incredible.
Conan O'Brien
He told me once, he was telling me about being in World War II. He's in Europe and the Germans are on the other side of the river. And he would mock them and they would yell back and mock him. They're just the soldiers yelling back across the river and him. And I thought, Mel Brooks fought Hitler for real. And the thing is, it's. No, this isn't a weird. It doesn't get more real than that. We talk about any comedian, I think, or artist who fought Hitler. They just. They're writing from a checkbook that I could never match.
Matt Gourley
Springtime for Hitler.
Conan O'Brien
Yeah. And it was such a big part of his work. And I know that there have been. I think he told me once that the producer was on stage in New York, was a massive hit, that someone once came down to the front of the theater and was screaming about, you can't do this. You can't, because it's making light of Hitler and everything. And I thought, but Mel Brooks can. Do you know what I mean? If anyone can, Mel Brooks can, because he's a Jew who fought Hitler. There's no politically correct in that situation with Mel or incorrect with Mel Brooks.
Judd Apatow
And I asked him, I said, was anyone else really going hard at Hitler like, the way you did? And he's like, I don't think so. Because you do think, like, who really went just hard at Hitler before him? I mean, Charlie Chaplin, I guess, before. Yeah, well, that started up, but there's not another guy who really was obsessed with.
Conan O'Brien
It's weird. A lot of performers and comics from that era were very pro Hitler. Yeah. Oh, no more than 60s, you know, laughing was really a pro Hitler show.
Judd Apatow
Red Skelton.
Conan O'Brien
Red Skelton. Oh, my God, he's gonna get us sued by an estate. I got sued by Red Buttons once because we did something in the very early, like the first weeks of the late night show. We did some clutch cargo and we did some joke about Red Buttons. That was just literally an aside. And the next day, news came on and they said, and when we come back, Red buttons sues Conan O' Brien for $20 million. That's how I found out. That's how I found out. The local, you know, Chuck Scarborough, the local news. Anyway, it all got resolved.
Judd Apatow
I paid him my Grandfather produced a Red Buttons album. And so when my grandfather died suddenly of a heart attack, I was like 16. And I'm at the. With the funeral and I'm just crying so hard. And in the middle of crying, someone walks over, goes, judd, this is Red Buttons. As like a comedy nerd, I was just like, red Buttons.
Conan O'Brien
You immediately stop crying.
Judd Apatow
Exactly.
Conan O'Brien
Red Buttons. Yeah. And how is Mel? I have to ask you.
Judd Apatow
I mean, the funny thing about Mel is his memory. Short term, long term, could not be better. So much better than mine. Like, mine is so bad. Like I'll like go to leave the house and get in the passenger seat and just sit there, you know, like I'm all scrambled. Like it's already happening.
Conan O'Brien
Right.
Judd Apatow
And Mel, he doesn't reach for a name from the 50s. Like, he's just incredibly sharp. So it was a great conversation. Cause he really can look back at it a hundred years and tell you about everything.
Conan O'Brien
Unbelievable.
Judd Apatow
And he's still crazy funny. Like, if he wants to be. He's right. He's right there. I remember me and Bill Hader went to visit him years ago. And then at the end of it, he goes, come again, but not soon.
Conan O'Brien
That's a great line. We don't talk enough about the unsung heroes of our show. You know, people know they're Matt Gourley. They know they're Sonam Obsessian. They certainly know they're Conan o'.
Judd Apatow
Brien.
Conan O'Brien
But I'm talking about the invisible co hosts. Our furniture.
Judd Apatow
Oh, yeah.
Conan O'Brien
I've done some shows in uncomfortable furniture. Yeah, terrible. You can tell the whole time that I'm in agony. That's why when Ashley offered to sponsor the Live from LA event, Anne said that Sona could choose the onstage furniture. We jumped at the chance.
Sonam Obsessive
Yeah.
Conan O'Brien
How did you do it?
Sonam Obsessive
Well, I am doing interior decorating now. I designed Blaze Place. I designed my parents place.
Conan O'Brien
You do have good taste.
Sonam Obsessive
So I was just like, hey, I want to do this. And it was surprising that no one said I couldn't. So I just choose whatever sofas I wanted, whatever chairs I wanted. Rugs, cute little side tables.
Conan O'Brien
Great. You used a tallora chairs and loveseat.
Sonam Obsessive
Yes, I did.
Conan O'Brien
And I was very comfortable throughout the entire show.
Sonam Obsessive
So was I. I mean, didn't you want to take a nap?
Conan O'Brien
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Roman Mars
That's good.
Conan O'Brien
I want to live to be 150 and still be wearing the same boots I put on when I was born. Bean boots carry that tradition forward. Handcrafted In Maine since 1912, built for outdoors, they handle rain, mud, snow. With over a century of timeless design, they don't chase trends. Each pair becomes more personal, more distinctive, and uniquely yours. L.L. bean boots are simply best worn. Find your pair@llbean.com let's talk about you and your career, because to discuss this book, we really need to go back to this interesting arc that you had, which is at the beginning, it's you wanna do standup, you wanna do standup comedy, you're a performer, and then you have this audition for Jim Henson. And I have to ask you about this because, well, it's just, it's fascinating to me. And you claim that this audition with Jim Henson is the reason you decided to not pursue standup anymore. Is that true?
Judd Apatow
It certainly was a key linchpin of the decision, but I was living with Adam Sandler in the valley. We had this little apartment and, you know, Adam would be on MTV every once in a while, or the Cosby show was, you know, one of the Theo's friends, you know, and there was this audition to be on a pilot where a couple of comedians would travel across the country. They were gonna give the comedians cameras and, you know, their own video cameras. Right at the beginning of when that seemed exciting. Like, we'll give them a camera, and they'll shoot it themselves. And so all these people were, you know, handing in their auditions that they would make themselves. And so me and Sandler went down to the beach with my grandmother and made some weird. I don't know what we did. And then I had a list of ideas of things you could maybe on the show. And I find out later that I didn't get it. But then they say to me, but he'd like to buy all your ideas. And then they said, but he didn't want you because he thought you lacked warmth.
Conan O'Brien
First of all, why tell you. Oh, and one more thing before you hang up.
Judd Apatow
And I just thought, this guy, as Kermit taught me to read, like, this is the warmest man. It's like Kermit telling you to fuck off.
Conan O'Brien
That's so great.
Judd Apatow
But in a way, I think he was right. Like, I was probably, like, repressed and self conscious and. And, like, he was smart enough to go, you know, like. Like, I could feel it when I was around Sandler, Jim Carrey as a kid. Like, they are just way looser than me and just charismatic. And I'm just, like, in my head. So I think it hurt me because I'm like, he got me. He knows I'm. I'm too shut down right now. And so then when writing opportunities came up, I thought, well, Jim Edson thought I should be a writer. I would just take the writing opportunities and do less of the performing things, I always think. And then he died. Yeah, like, not long after that. So I'm like.
Conan O'Brien
Before he could take it back. Yeah.
Judd Apatow
Like, I was so upset about it, and I'm just like, ah, God, what does he know? Jerk. And then they're like, he's dead. I'm like, oh. Like, he's the most important person in a young person's life. Sesame Street. I mean, I put in a billion hours watching it.
Conan O'Brien
So, yes, he sounded like Kermit when he spoke. Which makes it even worse, because it's Kermit sound saying, you don't have warmth. You don't seem like a warm person to me.
Matt Gourley
You lack warmth.
Conan O'Brien
Yeah. You lack Warmth. You're just not warm. Fuck off and die.
Matt Gourley
Go shine your shoes, you mutt.
Judd Apatow
I didn't get to clean it up with him later.
Conan O'Brien
I'm fascinated by the leap to directing. What made you think, oh, no, I will direct?
Judd Apatow
Well, I, you know, I went to college and studied screenwriting and took some directing classes and I was just so terrible. My films, I mean, if I think about them, I won't sleep at night about that. I showed them to people like, I. I couldn't even believe that the two pieces of film you would tape together, that you would see them and it would, like, change images. I was like. I was like a four year old and. And so I lost confidence in my ability to do it. I also had an irrational fear that I would get the eyelines wrong and I would cut a movie together and everyone would be looking in the wrong direction. Like. Like that probably made me not do it for 10 years. Was an irrational fear of.
Conan O'Brien
It is a real problem in your films. I've gone back even your biggest hits, no one's looking in the right direction. Very distracting.
Judd Apatow
And even now I don't know what the lenses do. You know, I always have to hire Janusz Kaminski to shoot it because I'm so bad that I need a really smart person. So I delayed it. When we did the Ben Stiller show, I never pushed to direct any of the sketches. I just was so afraid. And then I was working at Larry Sanders and then one day Garry Shandling just literally just walked in my office and goes, you're doing next week off of nothing great. No conversation.
Conan O'Brien
He threw you into the deep end of the pool.
Judd Apatow
Yeah, like immediately. And came down to set and helped me and was so helpful. And that was the first time that I ever did it. And I just had to figure it out. And then we did Freaks and Geeks and I did a bunch of those and a bunch of underclaimed.
Conan O'Brien
Confidence is growing.
Judd Apatow
Yeah.
Conan O'Brien
But once you start working with a huge budget and it's a movie, how terrified were you with your first. What was your first directing experience in a movie?
Judd Apatow
Well, I just worked as a producer on Anchorman, and that was McKay's first time directing a movie. And so it was really fun to be there and watch Adam go through the experience. And Adam was very improvisational. And so in addition to this amazing script he wrote with Will, he was doing what Stiller was doing, which is a lot of playing in addition to the script. So when we were doing the Four Year Old Virgin, I thought, okay, I'm gonna do that. Even with the dramatic scenes, I think there's something good could come out of riffing. But I remember, like, two days before we were gonna start shooting, I was just really nervous. And it's also Karel's the lead. So I'm going like, I think this is the guy.
Conan O'Brien
Yeah.
Judd Apatow
And I watched a TV show that Steve was on, like a sitcom that had been canceled, and they were burning off the episodes, like a terrible show. And two nights before we started shooting, I just watched an episode and I watched Steve and I went, oh, this could be that bad. Like, if I don't do a good job, I could make Steve look so bad. Cause this show made Steve look bad. And Steve's a genius. And it really, like, scared me to my core. Like, oh, there's a way to really be a terrible director. And so I just shot so much footage, like a million feet of film. I had Steve and everybody improvising for hours. The crew hated me. They were so bored. Like, it was the crew from the Unforgiven. It was literally Clint Eastwood's crew.
Conan O'Brien
And guess what? Clint Eastwood famously is a one take director. Do a take. And he has famously, like, well, it's five o'. Clock. Everyone go home now. They love Clint. And then you come along.
Judd Apatow
Yeah.
Conan O'Brien
And I'm like, fantastic.
Judd Apatow
And I'm doing like three hours of improv on, like, Steve peeing with a boner, you know, and the whole crew would look at me like, I can't believe. I can't believe this. And the dp, when he saw the finished movie, he just said to me, oh, now I see what you were doing. But they really did look annoyed. And that kind of made me scared. But I just thought, I just have to go into editing knowing that if it's not working, I have other stuff to fix it with.
Conan O'Brien
Whenever someone has a great success, they can actually send the wrong signal to other people. And I think one of the things you did is you made these terrific movies. You got all these really funny people. And yes, you had a good script, but you're also letting them play. You've got a deep bench. You're trying different combinations of things. And I think people started to watch your early films and think, oh, yeah, it's just letting people riff. And you think, well, if it's Jud and he's got all of his people and he knows exactly what he wants to get. Yeah. I think other people who don't know that world took that as, oh, that's how you do It. And then I remembered seeing just a ton of comedies where they would just let you know people who shouldn't be riffing. Walter Cronkite and Dame Edna. And they'd be just. It would be painful.
Judd Apatow
Yeah. Because if you can tell an actor thinks they're being funny, it instantly is awful. Like, if there's any self awareness of, like, this is really working. And so the cockiness of doing improv well, even if the jokes are good, like, takes you out of the scene. It only really works if people are so deep in character that when you're in editing, it could seem seamless. Almost like a documentary. Like, when it works, it's like, oh, this was like a documentary of peeking in on people. And when it doesn't work, it looks like someone thinks they're hilarious. And then that creeps you out, you know, like, you can't have that in it.
Conan O'Brien
I recently saw one of the Pink Panthers, which are my touchstone movies. Peter Sellers, Blake Edwards. It was one of the later ones. And I think it's a scene with Diane Cannon. And this is how clearly she was directed to do it. So it's not on her, but it's Clouseau's being Clouseau. Peter Sellers. And she's laughing and finding it really funny. And I was watching it with my son, this is a couple years ago, and both of us were like, oh, no, no, you can't. No one in the scene can think he's funny. This is. You know, someone just poured sewage into our soup. We can't eat this. Do you know what I mean? It was just so awful. But I loved that my son saw that too.
Judd Apatow
Who was the guy that played Clouseau's boss?
Conan O'Brien
Herbert Lum.
Judd Apatow
Oh, my God, is he funny?
Conan O'Brien
Oh, with the twitching eye.
Judd Apatow
Yeah.
Matt Gourley
You didn't get that out first, though. I noticed Conan got that out first.
Sonam Obsessive
No, I was helping.
Conan O'Brien
I thought she tried to jump in with Herbert Lom.
Sonam Obsessive
Yeah, yeah, yeah.
Conan O'Brien
And then she realized she doesn't know what we're talking about and she never, ever will.
Judd Apatow
Because I remember seeing being there. And at the end of being there, during the credit sequence, they show raw footage. I mean, we had seen, like, bloopers before in, like, Smoking the Bandit, but this was literally just a working, like, watching the dailies of him riffing.
Conan O'Brien
He's in the operating room and he's riffing. And you know who that really pissed off?
Matt Gourley
Herbert Lahm.
Conan O'Brien
No. Oh, good. But good guess. Okay, you're both idiots. I just want you to know we've been wondering, are you really idiots? But now the proof is in. You can tell your doctors it's been confirmed. No, they put that in. And Peter Sellers flipped out, and he said, this ruins the whole movie. It doesn't. But he's kind of right that he's created this character. And now you're gonna show a blooper reel at the end.
Judd Apatow
It shows that they were just so nervous. Cause the movie ends with him walking on water. And it's this very surreal ending. And then you cut to going. You tell Raphael, right? It's like this really funny, dirty.
Conan O'Brien
And it's basically him breaking up. He can't get through the speech without laughing. But he just was appalled that Blake Edwards put that in. I'm not Blake Edwards. I'm sorry. I forget who it is.
Judd Apatow
Hal Ashby Herbert.
Conan O'Brien
There you go.
Judd Apatow
But you could, because you would think, oh, you're gonna forget what the movie was about. But, you know, I had a similar thing at the end of this is 40. I had, over the credits, Melissa McCarthy and Leslie and Paul Ruddy in the principal's office. Because I just remembered Melissa riffing. Saying the meanest things ever to the principal was one of the funniest things I'd ever witnessed in any space. And so I put it at the end of the movie. I showed the movie to James Brooks, and he's like, what do you think about having those bloopers in there? Like, what do you think in there? As he should, right? He's like, do you think that kills the spell of the movie? And I said, well, I kind of feel like I've put people through a big emotional journey for, like, two hours, and this is, like, my thank you for hanging in with me. And he goes, all right, man. Okay.
Conan O'Brien
So you don't want to take my advice. I'm one of the most iconic comedy writer producers of all time and directors. But I just offered you some advice. Now you talk about Comedy Nerd is the title of your book. And this is interesting, because I didn't even know I was a comedy nerd when I was a comedy nerd, but. And now in retrospect, I see I was a comedy nerd. You were aware when you were a comedy nerd that you were, in fact, a comedy nerd.
Judd Apatow
Yeah, because I think people were into, like, sports, and I. You know, I like how you said sports.
Conan O'Brien
Like you're describing some inert gas out there on the end of the universe that no one's ever seen.
Judd Apatow
People were into athletics. I'd be nervous. And so the idea that I had found something that was just mine because no one else cared at all. I mean, even with Saturday Night Live suddenly coming on the air, it wasn't like there was anyone who liked it like 5% as much as me. But I also thought, oh, it's cool that I have a hobby that no one else has. And I also really liked the fact that no one liked it. And I also thought there weren't many people in the country who cared about comedy. So even as a little kid, I thought I could get a job. There's only seems to be about 100 people doing this on Earth. Maybe I could slip in if I really care about it.
Conan O'Brien
And you were living where, you were living on Long Island. Had you ever seen famous people when you were a kid? Because I had no exposure to any famous people. And that fueled my belief that this is something that couldn't be attained if you lived in Brookline, Massachusetts. Like, no, you can't do that. That's a different universe.
Judd Apatow
I had the opposite. My grandma was buddies with Tony Fields and she was like legendary comedian, kind of like a Joan Rivers self deprecating comedian. There's a really funny clip of her on YouTube on the Mike Douglas show. And the other guest is Gene Simmons from Kiss.
Conan O'Brien
Oh, Jesus, perfect.
Judd Apatow
And she goes, wouldn't it be funny if we found out that you were just a nice Jewish boy under that makeup? And he goes, and he kind of makes some comment like, hey. And then she just goes, yeah, I can tell from the hook. What?
Conan O'Brien
Jesus. Guessing she's Jewish as well.
Judd Apatow
Yeah, she is. She is.
Conan O'Brien
Okay.
Judd Apatow
She's allowed to, she was allowed to do that. Yeah, but so I went to see her as a kid and she had her leg amputated because she had diabetes. So she did this comeback tour where they, she came out like on a golf cart and they put her on the chair. And then she would do jokes about having had her leg amputated and she had all these funny jokes about going to get the spare tire out of the car at the gas station. The guy seeing her other leg, you know, it was all like riffing about and I, I remember getting standing ovations as like a 10 year old and, and thinking, oh, wow, she's made herself cool.
Conan O'Brien
Yes.
Judd Apatow
Like she's the coolest person in the world. This kind of like chubby lady with one leg and like people are adoring her. So I think somewhere in my head I'm like, that seems like a good, that was my, you know, 10 from your show of shows.
Conan O'Brien
Yeah. And then of course, you get into prior Steve Martin.
Judd Apatow
That's just, you know, well, that era. I mean, George Carlin albums were coming out, those Richard Pryor albums were coming out. So, I mean, it's kind of insane when you look back, like between 75 and 85, what happened? So if you were obsessed with it, you were just getting fed Monty Python and then Second City. And I just couldn't get enough of all of it. And then thought, well, I wonder how could I do something? Like, what would I do? And I didn't really have a take on what I would do. I just thought, oh, I'll be a comedian. And that was never going that great. It was going like, okay, I would do some of those evening at the improv shows. But then I met Stiller. And then we came up with the Ben Stiller show. And that's the thing that kind of switched the gear of the whole thing.
Conan O'Brien
It was also an interesting time. Cause we came up sort of in the same wave. There was much less comedy. It was a big deal when we were kids. I mean, now we are those guys from the 19, from the depression who were talking about, when we were kids, we'd gather around the curve top radio. But in the 70s, I would know that Marty Feldman has a weird comedy special that's gonna come out this summer. And there's only gonna be three episodes of it. My brothers and I would wait for was an occasion.
Judd Apatow
Yeah, you track it. Andy Kaufman is gonna be on Taxi. And you knew months in advance. Yeah. Now there's so much stuff. Like, people go, why don't people go to comedies? I'm like, because all they're doing is looking at good comedy, like on TikTok all day. And you could go, is it good or not? Yeah, it is. Like someone like, pooping in a hot tub is better than everything I've ever done. You know what I mean? Like, it's the funniest falling down joke. It's the funniest sex joke.
Conan O'Brien
That's what I keep thinking, is that you've given, essentially given however many billion people there are on Earth. And you know the answer.
Matt Gourley
Herbert Lomb.
Sonam Obsessive
Eight.
Conan O'Brien
Herbert Lomb.
Judd Apatow
Yeah.
Conan O'Brien
Yeah, there are. Herbert Lomb. Many people.
Roman Mars
Eight billion.
Conan O'Brien
Okay? Eight billion people on Earth. And let's just say. I don't know, let's just be kind and say 4 billion of them have a phone that can record. Or 5 billion have a phone that can record video. If you've got that many people out there, if one of Them is going to beat any professional comic mind because they were actually shooting their grandmother when a lightning bolt hit her and her wig went flying off and landed in the suit. And then they put a funny song to it. That's never gonna happen to that person again. But they have put that out into the universe. And you look at it and you go, oh, my God. It's the footage you've shown me of the mascot slipping on the fall. And I think I could get Judd, I could get all the funniest people I know. We could work really hard. None of us are gonna come close to mascot slipping on the ice while they're trying to inter interview him. It's just so funny. And the person who shot that will never do that again. But it doesn't matter because there's a couple of billion other people out there who are going to take a shot.
Judd Apatow
And we're competing against that. That's why I think, like, one of the things people like best from my movies is Carell getting waxed, because it is the equivalent of a YouTube video of just watching someone being abused. As soon as it starts, you're like, oh, geez, this is real. I could just see it. Like the audience, we didn't tell them it was real, but they literally could just feel it, you know, that's why I like Jackass is the funniest thing. You know, you just have to stop thinking you can compete with it and then just muddle about it.
Conan O'Brien
I'm determined to do a better stunt than anyone on Jackass and I'm gonna do it too.
Sonam Obsessive
Yeah, you should.
Conan O'Brien
Conan o' Brien died today.
Matt Gourley
If you just want me to punch you in the nuts, I'm happy to do it.
Conan O'Brien
You mean again?
Sonam Obsessive
We could take turns.
Conan O'Brien
Okay.
Sonam Obsessive
Yeah.
Conan O'Brien
Do you have the ability to be sentimental and really attached to just like all the experiences that you've had had in your career or have you worked on yourself because a lot of people can't. A lot of people are just. They stay in the moment and oh, I gotta get. I gotta make this work. I gotta. And I know that you work on yourself a lot. You read a lot of self help books and is this something you're working on to like trying to be able to access? I'm so lucky. I can't believe I get to do this. All that kind of stuff, I think.
Judd Apatow
You know, my parents never talked about anything with therapy or religion as when I was a kid. Like, nothing. They didn't bring it up. Although my dad did when my parents were getting Divorced. Leave out a book that was called Growing Up Divorce. Like, hoping I'd read it. So he just left it on a coffee table. And then.
Matt Gourley
His way of helping you is just homework.
Judd Apatow
Yeah. So we never talked about all the pain. And then one day, like, three years ago, I mentioned to him, like, you know, the only. You never talked to me. The only thing that even ever helped me is I found this book in the house, and it was a little helpful. He goes, yeah, I left that book out for you. And I'm like, you left it out? Yeah, I hoped you read it. And I'm like, well, you didn't ask me if I read it. Like, you didn't know that I read it. Yeah. But, you know, it got moved. It was in a different spot.
Conan O'Brien
This is what passed for a real heart to heart in our era, I think. When my mom was pregnant with my youngest brother, someone left a book out that was called Mommy and Daddy, you know, Are Having a Baby.
Judd Apatow
I remember that.
Conan O'Brien
And I remember when you get to the crucial part of how the baby was created, it's just a drawing of the mommy and the daddy lying in bed with their covers up to their chin, looking straight up at the ceiling, smiling. And it just says, mommy and Daddy had a nap. And you're like, they get to the crucial point. That is how your family does it. I know. Exactly.
Judd Apatow
Well.
Conan O'Brien
That is how we do it.
Judd Apatow
Oh, I have a very traumatic story about that, because that book was called Where Did I Come From? And it was like, funny cartoons of, like, a sperm and a top hat, you know, and then they say, you know, an orgasm is kind of like a sneeze, but different. And then it would show not your.
Conan O'Brien
Nose, but your dick. Jesus book.
Judd Apatow
They had, like, the mom naked with her boobs out. It was like. Some people call them jugs, some people call them titties.
Conan O'Brien
This is not. We're not talking about the same book. My book had none of this. I would remember. Remember a sperm with a top hat.
Judd Apatow
So this was the book in our world. And my friend had the book. And I was like, literally, like seven or eight. And I'm like, I need more time with that book. And so I steal the book and I take it home. And then my. My mom sees my knapsack. She's like, what's this book? And I'm like, oh, I took it out from the library. She's like, well, there's no library card thing there. I'm like, I don't know. Maybe they didn't put it on that one I don't know. Then she's like, you're lying to me. I'm like, I'm not lying to you. That's where I got the book from the library. And, you know, so then she's like, well, when your dad gets home, we're gonna have to deal with this.
Conan O'Brien
Oh, boy.
Judd Apatow
So, you know, and my dad comes home and he's just like, don't be a liar. Don't be a thief and a liar. And so my family didn't have the instinct to go, I think he wants to know the facts of life.
Conan O'Brien
He wants to know they are pursuing the wrong avenue. Where did the book. Where did the book originate? No, no, no, no. He's clearly crying out to learn about. Yes, yes, yes. But bookstore or library, stolen or borrowed?
Matt Gourley
I never left it out for you. In silence.
Conan O'Brien
It couldn't have been.
Judd Apatow
My dad comes home and then, like, I like, getting, like a spanking. I'm gonna give you a spanking. And I'm like, I didn't steal the book. And they're like, just say you stole the book and we won't spank you. And I'm. And in my head, I thought, I will never admit it, ever. Like, I. I literally, like, had an idea, like, never admit it, no matter what happens right now. And I just, like, took this, like, spanking.
Conan O'Brien
He'd be a good spanker.
Judd Apatow
And then my parents start, like, crying because they can't believe I'm so crazy that I won't admit I stole the book. And I'm like, John McCain in the Hanoi Hilton.
Conan O'Brien
To compare your experience with John McCain at the Hanoi Hilton is treason, sir.
Judd Apatow
And finally my dad's just like, if you just admit it, we'll never spank you again. And I went, yeah, I stole the book. And then they never spanked me again.
Matt Gourley
What a good deal you got, though, man. You really won that negotiation.
Judd Apatow
But that's how you become the guy that makes the 40 year old virgin.
Conan O'Brien
Yeah.
Judd Apatow
You know, that kind of trauma just lives in you.
Conan O'Brien
There are so many. Jason Segel's character in Knocked Up, I remember having that moment of seeing that in the theater. And there was so much I loved about that movie and still do. But his character, the way he talks to Katherine Heigl and says, like, oh, the. You know, talking about her body. And it's. He's actually being quite warm, but it's also. He's not. I don't think he's crossing a line, but he's on a line and he's kind of crossing it.
Judd Apatow
It's douchey. Yeah.
Conan O'Brien
But the other thing, too, is, like, he's just so. And because he's so lovable and sweet, he's the perfect guy to do it. But I thought, oh, this is new ground. Like, I haven't seen anyone do this guy before.
Sonam Obsessive
I think he said, I see the milk came in.
Judd Apatow
Right?
Sonam Obsessive
Wasn't that one of his lines?
Conan O'Brien
Yeah. Which if.
Sonam Obsessive
You know, if someone said that to me, I'd be horrified. But I'd also be like, I'm impressed that you know that.
Conan O'Brien
Oh, no. He knows so much about what a woman goes through, and he's saying it with such empathy that you have to remind yourself, he's a guy. He. But, I mean, it's.
Judd Apatow
Well, it was funny because when we were shooting Knocked up, you know, we had gotten canceled with Freaks and Geeks and Undeclared, and I felt really bad. Cause I thought all these people are so great, and we keep getting kind of crushed by people. So when they said, okay to Knocked Up, I'm like, oh, I could make all of Seth's friends. Everyone I think should be a star.
David Melmed
Right?
Judd Apatow
And just like. And in one movie, if I can make them all funny, then they all can, like, work and do cool things. And so everyone was very aggressive. So it was almost competitive on set. You know, I would even have sometimes have two people do the same scene and go, hey, let's just see who does it funnier. Like, it was kind of not even nice. Looking back, it was Gladiator days. Yes. But everyone was a lot of high energy. And then Siegel was doing this kind of mellow, douchey guy. And I remember thinking, I don't know if this is working, but I'm gonna just go with it. And then I got into editing, and I realized, oh, he had countered the vibe of everyone else. And everything he did, he's playing a.
Conan O'Brien
Different part of the guitar neck. Like, he's getting a different. He's in a different register completely from everyone else, which is fantastic.
Judd Apatow
Yeah. No, so, so funny. Jason was always the funniest to deal with. Like on Freaks and Geeks, when he was miserable in love with Linda Cardellini. And you knew if you asked him to sing lady to her and make her cringe, he just was so hysterical doing it.
Conan O'Brien
Yeah. And he really is that sweet when you hang out with him or talk to him, he's got that sweetness. He can access that.
Judd Apatow
It was funny the other night, seeing Siegel and Seth at the Emmys, like, sitting in the front row next to Harrison Ford. I'm like. I was, like, so excited.
Conan O'Brien
Something's been a fold in the universe. I think one of the big lessons that comes away from me when I talk to you or flip through your book is my favorite part of this whole business has been collaboration. To me, that's the great scam of this business. It's madness that you get to be around these people. And it's just. It feels like I should have paid for the privilege, you know?
Judd Apatow
Yeah. Cause you love it so much. Like, I've been editing a documentary about Norm MacDonald, which will be on next year. So I've watched all of his clips with you, and they're just. They're so good. You kind of can't believe how many times something magical happened on the show. You don't realize till you kind of really line up all the things Norm MacDonald did, how many times he did some breakthrough, riotously funny thing. But the thing that I was delighted about while making the documentary is when you go through his whole life and you go through all the clips. There was a simplicity to Norm, which is he loved comedy more than anything. Like, comedy and his family. And that was kind of the main thing. And he just loved to make you laugh, like, more than almost anyone, where you go, oh, that was just the whole thing to him. In fact, I think he said, well, maybe it was like Jon Stewart was talking about this, and maybe I'm conflating it, that Norm loved his joke so much that he didn't care how you reacted.
Conan O'Brien
Oh, that's the other thing. I mean, I remember this so clearly, Norm being on the show and being fantastic. But he had more nerve than anyone I've met in comedy. So he's done, and he leaves the stage, the band's playing, and Andy leaned over and said, norm doesn't care in a way that frightens me. And I was like, that's exactly it. It's just terrifying because he will. He just. And you can see him on Update. All those times, he would lean in and hold the camera.
Judd Apatow
Yeah. If the joke doesn't work, he slows down.
Conan O'Brien
He slows down. He's not gently speeding up to get onto the next one. He is. And he just. I don't know. He was a magical, magical person who somehow knew. I won't be here long. I apologize to no one. This is how it should be done.
Judd Apatow
Yeah. Because when I was a kid, the dream was like, could you ever be around Bill Murray or Gilda Radner just to even watch it? Happen. So sometimes I think the only reason why I ever did anything was just to be able to watch all the work I ever did was just to sit in a chair on the anchorman set and watch them sing Afternoon Delight. Like, oh, I found a way to have credibility to be a fan.
Conan O'Brien
Yeah, yeah, it's a lovely thing. I just always think this is a dodge of some kind. We snuck our way into this thing and soon they will find out and escort me out. But I'll take it. The book is called Comedy Nerd and it's a delight. It's just so nice to have all of this here and even just flipping through it, you get hit with so many images of. Hilarious moment, hilarious moment, hilarious moment.
Judd Apatow
You know, and there's photos of you and there.
Conan O'Brien
I know I didn't. And I didn't clear them.
Judd Apatow
The money goes to fire charities.
Conan O'Brien
Now that I'm suing you, the money.
Judd Apatow
Goes to me and 826.
Conan O'Brien
Yeah. Breaking news. Conan O' Brien taking fire funding, much needed fire funding, over a small dispute with Judd Apatow. And you've got all these. You're constantly making these documentaries, which. This is a new thing for you. I mean, you're. The first one I think you did was Garry Shandling, is that right?
Judd Apatow
Well, the first one was 30 for 30 about Dwight Gooden and Daryl Straub.
Conan O'Brien
Yes, that's right. That's right. But I think the first comedy one was what you did for. And I think I told you at the time, this is a mitzvah for Gary because Gary really, really deserved the full treatment. And you gave it to him. And then I'm looking forward to all these other ones. And I'll be in some of them.
Judd Apatow
I suppose you're in a lot of them. Talking about Elvis during the Maria Bamford documentary.
Conan O'Brien
He just. Elvis just had a thing known as Maria Bamford. I'm just ta ta, ta da da. Maria Bamford took black music and white music and fused them at a time after World War II. All right, go with God. That's what I say to you.
Judd Apatow
Thank you.
Conan O'Brien
As a T Mobile member, you can take the perks with you because you're traveling with magenta status.
Sonam Obsessive
That's cool.
Conan O'Brien
I love saying it.
Sonam Obsessive
I know. I could tell.
Conan O'Brien
Ask me my status.
Sonam Obsessive
Hey, Conan, what's your status?
Conan O'Brien
Magenta status. It starts the moment you take off with free inflight WI Fi so you can stream your favorite show on the go. Plus, you're covered with 15 gigabytes of high speed data in over 215 countries and destinations with experience beyond plan.
Sonam Obsessive
That's cool, man.
Conan O'Brien
This magenta status sounds amazing. Blay, tell me. I think you get magenta status. What's it entail? What's included in magenta status?
Matt Gourley
Yeah, I have T Mobile.
Conan O'Brien
I have had T Mobile for a long time. I love it. And you know, when we went to Thailand, I got great coverage and great high speed data, which means that I could. I hear it's up to 15 gigabytes.
Judd Apatow
That's right.
Conan O'Brien
How did you know? That's the word on the street. Wow. I hear people going 15 gigabytes. Yeah, that's incredible. Yeah, but it was great. I was connected and it really helped. Well, this sounds great. Find out how you can experience travel better@t mobile.com TravelToday qualifying plan required. Wi Fi where available on select US airlines. Terms and conditions apply. Fall is here and that means fall close. I love fall close. Me too.
Matt Gourley
But this is something we really agree on.
Conan O'Brien
Well, this is something we really got because I like to cover as much of my body as possible and most people agree I should. Macy's Fall Fashion Guide is your one stop shop for the season's biggest trends curated by Macy's style experts. Think weekend in the country. The new boho and statement luxury. For her that means romantic flowy dresses from Cece, sheer looks from Inc. Luxe leather by Donna Karan and Karl Lagerfeld and bold animal prints from Anne Klein, Steve Madden and more for him. Well, Levi's bomber jacket, vintage inspired denim statement loafers and relaxed suiting from Hugo Boss and Michael Kors. Shop now@macy's.com or in store today. We're back part two with fake lawyer David Melmed who works here at Team Coco.
Matt Gourley
We're talking to him about music rights.
Conan O'Brien
We are talking. I was gonna get there. Sorry. Because this is a different episode.
Sonam Obsessive
Many other things too. I mean, you. You devoted a huge chunk to how good looking you are.
Conan O'Brien
Unlike a certain lawyer. I don't drone on.
Sonam Obsessive
Unless you're talking about how attractive he is.
David Melmed
Well. And you're being built so we can talk as long as your meter's running.
Conan O'Brien
Absolutely.
David Melmed
We can go all day. We can go all day.
Conan O'Brien
Fortunately. All day, buddy. I love that. I'm gonna get a bill tomorrow for $900. Keep going.
David Melmed
I love this.
Conan O'Brien
David Melmed is his name. He does a wonderful job here at Team Coco. And we had a legitimate question. We're following up this previous conversation we had. This is part two. Can we sing popular ditties on the show? Even if we're singing them badly out of tune using incorrect lyrics, do we still have to pay? And David, your answer was maybe. And the thing that got my attention is that you say, whatever happens, you have to start making phone calls and writing emails to people to ask if we can buy it. Which is sounds draconian to me.
David Melmed
It can be, but it's also, you have to look at what you're trying to clear. So you mentioned Led Zeppelin, Beatles, Michael Jackson, Brittany. I mean, these are iconic bands. Music. If you were, let's say, in that band and that. And you created this original work. Right. You would not say you necessarily want to be compensated for it, but certainly credit. And that's something that you have brought into the media space that you are protecting. Right. Okay, so I think you had mentioned Conan before of. Wouldn't you want your material out there being promoted? Wouldn't you want to be on the Conan o' Brien Needs a Friend podcast of music? It depends on who you're trying to copy, if you will.
Conan O'Brien
Okay, I'll be Paul McCartney. Sure. You've called Paul McCartney because I sang a quick snippet of Let It Be. You call me.
Judd Apatow
Hello?
David Melmed
Sure. Paul McCartney came on your podcast.
Conan O'Brien
No, I'm doing it. I'm doing it right now. David, I understand this is a roll improv. This is a role play.
Sonam Obsessive
I understand.
Conan O'Brien
Are you a lawyer and not a comedian?
David Melmed
I wouldn't be talking to Paul McCartney.
Conan O'Brien
But if I had been, listen, I would be cold. Your improv skills are terrible. I would not be talking to him. That would not happen in this scenario.
David Melmed
But if I was.
Conan O'Brien
Okay, that's what we're doing right now.
David Melmed
Yes.
Conan O'Brien
You just rang the phone.
Matt Gourley
Hello?
Conan O'Brien
Who's here? Who's there? Hello? Is this a telephone? Who's here? Who's on the phone? Is this. I just picked up me phone and I was wondering. It went all jingly wingly and I picked it up. Who's there? Please identify yourself.
David Melmed
This is David Malmed with Team Coco SiriusXM. I work with Conan O'. Brien.
Conan O'Brien
Oh, Conan O'. Brien. He was on the. I was on his podcast, I think, and he's interviewed me. I've interviewed him a few times. He's a very good musician and singer. What was your question?
David Melmed
My question is we would like to use few seconds of your Let It Be.
Conan O'Brien
Oh, that's not fucking happening. No fucking way. No, that's a song I wrote and that's a big song. 1969, Paul. It was on Let It Be and you know, I Just had a little tune in my head and I came in, he said, hey John, what do you think? Let it be. And he was like, I don't know. Oh, that's LA swinger. And Rickett was like, I'll just play the drums. And then George was like, oh, I'm kind of grumpy. And then say, no, we made it in a civil, so no, I wouldn't. What do you want to do? To let it be? What do you want to do?
Matt Gourley
Hi, this is Michael Jackson. I think I actually own all the rights I'm willing to sell.
David Melmed
That's a great point.
Conan O'Brien
Oh, I forgot to mention that I'm here having tea with Michael Jackson's ghost, so. Oh, by the way, boo. That's not so scary now, is it?
Sonam Obsessive
Boo. He would say boo hoos.
Conan O'Brien
So it's so funny. I never knew Sona was the super funny one, but she is. She's like the funniest one on this podcast. And she was just Conan's assistant. I'm kind of a deep fan. I go really deep on this stuff.
Sonam Obsessive
What?
Conan O'Brien
Paul, you know who I am? Oh yeah, you're hilarious.
Judd Apatow
Oh cool.
Conan O'Brien
I remember you were on the tour and you've done a lot of funny videos with Conan. I follow you religiously and hey, shout out to the Armenian community.
Sonam Obsessive
Oh my God.
Conan O'Brien
Yeah, I'm sorry about your book, Michael. Could you just lay back a little bit?
Matt Gourley
Sure.
Conan O'Brien
Okay, so I'll be over he here. Oh, he just walked out of the room backwards. Something he does, you know, with the Beatles. We just sang the songs. We didn't do all the leaping and the jumping around, but he did it really well, so. Listen, David Melmod, do you mind if we switch to Zoom for a second? Because my line isn't so good. Can we switch over to Zoom?
David Melmed
Absolutely.
Conan O'Brien
Can we just. Oh your handsome.
David Melmed
Thank you. Thank you, Paul. Oh, much appreciated. Does that change your opinion on.
Conan O'Brien
You got like a golden glow. And I don't fancy. I don't fancy the fellas too much, but I gotta say you're a very good looking. Thank you. You might not be a lawyer. I've heard it's in question. You're a very good looking fellow.
David Melmed
Thank you. Does that change your.
Conan O'Brien
Oh, not at all, no. The law's the law. Do you mind on doing that one button? Just don't do it just a little bit, David.
David Melmed
Whatever it takes to get these cleared. Okay, so you know what I would say?
Conan O'Brien
You know what I'd say?
Judd Apatow
Whatever.
Conan O'Brien
Now the lawyer's the funny one. The assistants, the funny one, the lawyer. Sawyer's the funny one. And where's Conan and all this? He's been quiet for a while. Haven't heard him. I guess he makes all the money. He's out counting the money. Oh, I got mixing pounds. I make some pence. David, I got to go. But no, you can't have Let It Be. It's no way. It's a special song to me. Unless it's something Conan wants and then I'll do it instantly.
David Melmed
There you go. Okay, Much appreciated. We are gonna send you a sample, Paul, of Conan singing Let It Be in his form. And I think we're gonna change your tune.
Conan O'Brien
You know what?
David Melmed
No pun.
Conan O'Brien
Cut to the chase, David. I give you oral permission right now, and I'd like to give you oral another way. And if it's okay. If it's okay. If it's okay. I'd also like to from this point on, give Conan a songwriting Credit. It's Lennon McCartney and O' Brien on Let It Be.
David Melmed
Fantastic.
Conan O'Brien
I think what he's doing is a bang up job. He surrounded himself by people who are very funny.
David Melmed
Let me write. I'm writing this down, Paul. Thank you.
Conan O'Brien
Well, anyway, I gotta sign off now and turn it back over to Conan.
Judd Apatow
He's.
Conan O'Brien
What a career. What a career arc.
David Melmed
Fantastic.
Conan O'Brien
I love. Yeah, he's great.
David Melmed
He's amazing.
Conan O'Brien
I'm gonna go now.
David Melmed
Okay, thank you.
Conan O'Brien
Okay. Doop dee doo. Oh, that's a good song. I think I'll write that down. That could be pretty good. Doop dee doo, Doop dee doo. Let's put that out. Okay, I'm back.
Judd Apatow
Okay.
David Melmed
I would say that would give. Get me nowhere. And I'll tell you why.
Conan O'Brien
Because it's oral?
David Melmed
No.
Conan O'Brien
Oh, boo.
David Melmed
Because it's Paul and it. Okay.
Conan O'Brien
Oh, I see. You need it from the actual people who.
David Melmed
Now if he wrote, you know, we need the publishers, so we need the writer. So I assume Paul and who else wrote Let It Be. Help me out here.
Conan O'Brien
Lennon. I mean, McCartney wrote it, but it's back in the Lennon McCartney days. Sure. O.
David Melmed
We would go to Lennon's estate, right? We'd have to go Paul. Okay, Paul's great. Let's do it. Then we'd have to go to John Lennon's estate. Then we would have to go to the record label and say, hey, we would like to do this.
Conan O'Brien
What a nightmare. What a nightmare.
David Melmed
It's a nightmare. I'll tell you what's.
Conan O'Brien
I hate your life. I mean. And you know what?
David Melmed
You know What?
Conan O'Brien
I wish you had a better life because this is an awful job.
David Melmed
Well, you know what? It's prob. You know what? It's actually problem solving, because I'll tell you why I like doing it. Because if. If you come to me and say, we want to do this, I think my joy is to try to make that happen.
Conan O'Brien
Happen.
David Melmed
It really is like, I.
Conan O'Brien
It's good for you.
David Melmed
It is. I. I really. Because once we get down to step 12, and I can. I have not been able to convince you to do something else. And you say, look, Conan wants to do this, then you just try to make it work.
Conan O'Brien
This is amazing. And can I.
David Melmed
Can I not my money.
Judd Apatow
Can I just chime in with a genuine statement that David is to his credit, and this is he. Everyone loves him for a lot of reasons, but one of the reasons is that he is a genuine problem solver anytime you come to him with an issue.
Conan O'Brien
Can I say something? At Team Coco, there's a lot of people around who just want to bitch and moan and make problems. You are the rare person who actually gets in there and tries to solve a problem.
Matt Gourley
You're like a fixer.
Conan O'Brien
You could get rid of a barrel.
Sonam Obsessive
Morale booster for the team.
Conan O'Brien
Oh, I think, you know, I want to call this company dead weight. 90% is just pure rot, you know, and everyone's just bitching and moaning all the time, and Jeff's back is out again, and, you know, whatever. I don't want to hear it. Everyone shut up.
Sonam Obsessive
Can you just. If he does do something and someone calls and says, hey, he used our music, can you just be like, no, he didn't.
Conan O'Brien
Yes. What about. What about lying?
Sonam Obsessive
Yeah, just lying or hanging up on them or, like, just avoiding it completely.
Conan O'Brien
What are you talking about? This is a pizza place. You know, that kind of thing.
David Melmed
So. So you're saying that a podcast that goes out to what, a million we get?
Matt Gourley
What million?
Conan O'Brien
Our numbers are way higher than that now.
David Melmed
4 million. Whatever.
Conan O'Brien
You're on our side. I. I don't.
David Melmed
I don't really follow the numbers or even listen, but I'm just.
Conan O'Brien
I know it's a lot.
Judd Apatow
I know it's a lot.
Conan O'Brien
I want to be biggest podcast in the world. Okay.
David Melmed
Biggest podcast in the world. And you're saying that wasn't Conan?
Conan O'Brien
Yeah.
David Melmed
Right?
Sonam Obsessive
Yeah.
David Melmed
I don't know if that would fly.
Sonam Obsessive
Okay, so I would do.
Conan O'Brien
I want to say that I have just made some jokes today about, oh, you're not a real lawyer. You are a lawyer. You're a terrific Lawyer. We're lucky to have you. I'm going to double down on maybe the best looking guy on staff. Sorry, Blay, but Jesus, Mary and Joseph, you know. Thank you.
David Melmed
I try to get on as many zooms and meet in, you know. It does help conversation. It does help conversation. It does.
Conan O'Brien
It would help.
David Melmed
Does Paul went.
Conan O'Brien
I don't know what's going on in your personal life? What's happening there? Stop. What?
Sonam Obsessive
You can't ask these questions.
Conan O'Brien
Hey, and guess what? If you don't answer me, I'll fire you. What are you going to do about that?
David Melmed
I'll tell you what I'll do with that. I actually work for Sirius XM now, not Team Coco. I don't know if you can fire me.
Judd Apatow
Kono.
Conan O'Brien
Phone call to Mr. Scott Greenstein. There you go.
Matt Gourley
It's okay for you guys to have a relationship.
Conan O'Brien
Hey, if you work for SiriusXM, we can have a relationship.
David Melmed
We can. My personal life.
Conan O'Brien
Oh, eight. Out of control.
Sonam Obsessive
Out of control.
Conan O'Brien
David, I applaud you. I applaud your good works, your golden hue and everything that you do for this podcast.
Sonam Obsessive
Your golden hue.
Conan O'Brien
He does. He's like a Renaissance. He's a Renaissance painting. I don't know how they let him out of the Louvre without setting off an alarm. David Melmed, our thanks to you. Thanks for clearing this up. And I guess we.
Matt Gourley
Yes, clearing it up.
Conan O'Brien
We can't sing a song.
Matt Gourley
I'm no closer to understanding.
Conan O'Brien
We can't do anything.
Matt Gourley
It's good, though. I think that's where we should leave it, because we have plausible deniability if he educates us too much.
Conan O'Brien
I consulted my lawyer and I'm still confused. What are you going to do? Sue me? Oh, absolutely, David. Thank you. Yes, thanks for having me.
Matt Gourley
And when they go, you, sir, you stole our money. And it's here on this podcast. And you go, I wasn't listening to that. I was too busy sexually harassing my lawyer.
Conan O'Brien
That's your defense, sir? I was busy making my lawyer very uncomfortable. So you don't have a leg to stand on.
Matt Gourley
And what a leg.
Conan O'Brien
Yeah, I didn't get started on his calves. All right, peace out, Tupac. But not gonna say any of the song.
Matt Gourley
Conan o' Brien needs a friend with Conan o' Brien Sonam of Session and Matt Gourley producer produced by me, Matt Gourley executive produced by Adam Sachs, Jeff Ross and Nick Leow Theme song by the White Stripes. Incidental music by Jimmy Vivino. Take it away, Jimmy. Our supervising producer is Aaron Blair and our Associate Talent Producer is Jennifer Samples. Engineering and mixing by Eduardo Perez and Brendan Burns. Additional production support by Mars Melnick Talent booking by Paula Davis, Gina Bautista and Brit Kahn. You can rate and review this show on Apple Podcasts and you might find your review read on a future episode. Got a question for Conan? Call the Team Coco hotline at 669-587-2847 and leave a message. It too could be featured on a future episode. You can also get three free months of SiriusXM when you sign up@siriusxm.com Conan and if you haven't already, please subscribe to Conan O' Brien needs a Friend wherever fine podcasts are downloaded.
Judd Apatow
Hi, I'm Roman Mars, host of 99% Invisible. It's a podcast about all the thought that goes into things most people don't even think about. You're going to see stories everywhere. Follow and listen to 99% invisible wherever you get your podcasts.
Roman Mars
For adults with Crohn's disease or ulcerative colitis symptoms, every choice matters. Trimfya offers self injection or intravenous infusion from the start. Tremphya is administered as injections under the skin or infusions through a vein every four weeks, followed by injections under the skin every four or eight weeks. If your doctor decides that you can self injectrum via proper training is required. Tremphya is a prescription medicine used to treat adults with moderately to severely active Crohn's disease and adults with moderately to severely active ulcerative colitis. Serious allergic reactions and increased risk of infections and liver problems may occur. Before treatment, your doctor should check you for infections and tuberculosis. Tell your doctor if you have an infection, flu like symptoms or if you need a vaccine. Explore what's possible and ask your doctor about tremphya today. Call 1-800-526-7736 to learn more or visit tremphiradio. Com.
This episode brings back acclaimed director, writer, and producer Judd Apatow for a candid—and frequently hilarious—conversation with Conan, Sona Movsesian, and Matt Gourley. They explore Judd’s new book, Comedy Nerd, swap stories about comedy nerddom, creative anxieties, nostalgia, aging in comedy, and the art and pitfalls of improvisational filmmaking. Plus, there’s a sidesplitting segment with Team Coco’s legal counsel, David Melmed, role-playing music copyright scenarios. The episode is a rich, sprawling blend of industry insight, personal reflections, and unrepressed improvised comedy.
[02:22–05:14]
“You can listen to it on this very friendly crime fighting level. And then there’s all the nuances that we pack in here.” — Conan [04:15]
[04:43–08:12]
“I had an idea about two and a half years ago that ads could be inserted dynamically.” — Conan [05:26]
“We were the first to do it.” — Judd [06:23]
“You were kind of sexualizing it too, a little bit.” — Sona [08:21]
[12:13–18:53]
“I also finished it and thought it’s so long that it feels like a textbook about workaholism.” — Judd [14:37]
“Just by being older, you’re creepy. You know, if I just go into a dance club and do nothing but stand there...people will call the police.” — Judd [16:54]
“It’s the less you do that’s creepy.” — Matt [17:21]
[18:53–23:54]
“Mel Brooks fought Hitler for real. We talk about any comedian…who fought Hitler. They’re writing from a checkbook that I could never match.” — Conan [20:40]
[38:18–41:53]
“She’s the coolest person in the world...people are adoring her.” — Judd [41:03]
[41:53–43:56]
“If you’ve got that many people out there, one of them is going to beat any professional comic mind…” — Conan [43:24]
[27:50–35:24]
“It’s like Kermit telling you to f*** off.” — Judd [28:52]
“I just shot so much footage…The crew hated me. The DP, when he saw the finished movie, just said…‘Oh, now I see what you were doing.’ But they really did look annoyed.” — Judd [33:33]
[35:24–38:18]
“Because if you can tell an actor thinks they’re being funny, it instantly is awful.” — Judd [34:50]
[44:35–49:05]
“My parents didn’t have the instinct to go, ‘I think he wants to know the facts of life.’ They’re pursuing the wrong avenue.” — Conan [47:54]
[51:47–54:05]
“Norm doesn’t care in a way that frightens me.” — Andy via Conan [53:17]
[58:26–68:38]
“That’s not fing happening. No fing way. No, that’s a song I wrote…and you want to do what to ‘Let It Be’?” — Conan as Paul [61:31]
“He is a genuine problem solver anytime you come to him with an issue.” — Judd [65:57]
The entire episode maintains Conan’s signature playful, self-deprecating, fast-paced tone—peppered with surreal tangents, improvisational chaos, and heartfelt reflections. Judd blends openness about his vulnerabilities and anxieties with whip-smart comic timing. Sona and Matt act as ideal comedic foils and supporters. Even the legal segment—ostensibly dry—erupts into parody and improvisation befitting the show's spirit.
This packed episode is more than a recounting of showbiz memories; it’s an affectionate, meta-comedy exploration of creative anxiety, generational change, and what it means to be a lifelong “comedy nerd.” For those fascinated by the craft of comedy—as a performer, creator, or fan—it offers eye-opening, frequently uproarious exchanges, industry secrets, and a masterclass in making friendship (or at least playful friction) out of professional collaboration. And if you’ve ever wondered what happens when a lawyer tries to explain music rights to comedians, you’re also in for an unforgettable treat.