Jimmy Kimmel: Making Late Night A Family Affair

Transcript

TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. It's late-night week on FRESH AIR. Tomorrow we'll feature an interview with Jimmy Fallon, who will be the new host of "The Tonight Show" after Jay Leno retires in February. And Friday we'll hear from Questlove, who leads the band The Roots and will move with Fallon to "The Tonight Show."

Today we have the interview I recorded with Jimmy Kimmel last January, just after his ABS show "Jimmy Kimmel Live" moved from the midnight slot to the very valuable time spot, 11:35, the same time as "The Tonight Show" and David Letterman. As we'll hear later, Letterman is one of Kimmel's idols, and Kimmel paid tribute to him when Letterman received a Kennedy Center honor last December.

Kimmel got his start in radio, then moved to TV and became nationally known for his work on Comedy Central as a host of the game show "Win Ben Stein's Money" and "The Man Show." He started hosting "Jimmy Kimmel Live" in 2003. Comedy bits from the show, which often feature members of Kimmel's family or celebrity guests, often go viral. Last year, he hosted both the White House Correspondents Dinner and the Emmy Awards.

Jimmy Kimmel, welcome to FRESH AIR. What's the symbolic value for you of being at 11:30 compared to 12:30, and, you know, what does that mean to you?

JIMMY KIMMEL: I like that you put it that way because I think the symbolism is probably more important because of Johnny Carson and because of "The Tonight Show" being on at 11:30. And so it's a big deal for me, it is. I mean, it's something that as a kid I was very interested in, and it's like being a baseball fan all your life and getting to be an announcer.

GROSS: How old were you when you were allowed to stay up to 11:30 and watch "The Tonight Show"?

KIMMEL: I don't know that I ever asked permission. My parents, we had - most of my life we had a little 12-inch black-and-white television set, and somewhere, sometime - I think I was in junior high school, my mom went to Macy's and bought a full-size color TV set, and she expected my dad to be angry when he got home, but he wasn't.

And I took the little TV set right to my - to my room - my office, I thought of it as an office. But I put it on my desk, and I never saw my family again.

(LAUGHTER)

KIMMEL: That was it.

GROSS: You're so relaxed on your show, but it sounds like you're very obsessive about putting it together. Rolling Stone, the cover story about you in Rolling Stone, described you as transcribing the other late night hosts' monologues to make sure there's no similarities between your monologue and theirs. Can you talk a little bit more about why you or your staff transcribes those monologues, what you do with them?

KIMMEL: Yeah, it's not me personally. It's our staff - we have one poor guy who has to sit there and write all this stuff up every night. I just don't want to repeat jokes that have been on other shows. I don't want to be accused of stealing jokes from other shows. And I just kind of want to know what they're doing.

I don't go through and read that stuff unless somebody says hey, this looks a little bit similar to what Conan is doing. And then I'll look into it, or a joke that was on "Saturday Night Live" this week. But it's mostly because I think it's important to be original. I just - I would hate the idea that people think we're stealing jokes. So I want to make sure that we don't, even if it's an accident.

GROSS: You did a whole show in character as Jay Leno. What separates your monologue from his monologue, do you think?

KIMMEL: They're not that much different. I mean, truth be told, we're talking about current subjects. We're talking about people in the news. We're talking about the big stories. I think that - you know, I try to imagine, when I write a joke or when I look at a joke one of the writers have written, I sometimes will imagine it in Jay's voice, and if I can, I'll generally throw it out.

(LAUGHTER)

GROSS: That's interesting. OK, so you were one of the people who paid tribute to David Letterman at the end of 2012 when he received a Kennedy Center Honor, and it was a really beautiful and funny tribute that shows how much he means to you and how he's affected you as a comic and as a host. So I just want to play your tribute to him.

(SOUNDBITE OF KENNEDY CENTER HONORS)

KIMMEL: In February of 1983, when "Late Night with David Letterman" went on the air, I was 15 years old and lucky enough to have a little black-and-white TV set in my bedroom. And every night after my parents went into their room to molest each other...

(LAUGHTER)

KIMMEL: I'd stay up late, secretly watching Johnny Carson. And then I started staying up later to watch the guy who went on after him. And while I loved Johnny, I fell in love with Dave. When I turned 16, I blew out the candles on a "Late Night with David Letterman" cake that my mom made me. My first car had a "Late Night" vanity plate. I drew pictures of Dave on the covers of all my textbooks.

(LAUGHTER)

KIMMEL: I started a "Late Night with David Letterman" club in high school. To me it wasn't just a TV show, it was the reason I would fail to make love to a live woman for many, many years to come.

(LAUGHTER)

KIMMEL: Every night, I wanted to be David Letterman. All my friends wanted to be David Letterman. Ironically, the only person who didn't want to be David Letterman is David Letterman. And that is a shame because you, Dave, are the funniest, the smartest, the weirdest, the coolest and the best one ever, hands down. And the greatest thrill of my career came last month when Dave agreed to be a guest on my show.

He could tell I was nervous, so right before the show he came to my dressing room and just held me.

(LAUGHTER)

KIMMEL: But Dave, whether you like it or not, you are my hero, and you are a hero to most everyone in this room with the possible exception of the people who came to see the ballerina.

(LAUGHTER)

KIMMEL: No one will ever measure up to you. It's impossible because we wouldn't know how to do this without you. You taught us, you inspired us, and most of all you made us laugh really hard. Thank you, Dave.

(APPLAUSE)

GROSS: That was a really beautiful tribute. That was Jimmy Kimmel paying tribute to David Letterman. What did you do in the David Letterman club that you founded?

(LAUGHTER)

KIMMEL: Well, he used to do a Friday night show every once in a while, once every three months, and we would have - I'd have people over to the house. Paul Shaffer used to sing a song, it was this little stupid thing, and he'd say (Singing) Bermuda, it's a cuckoo, nutty place.

And so I decorated my house to look like Bermuda for one of these parties.

(LAUGHTER)

KIMMEL: We'd - I'd recreate props that I'd seen on the show. There was - they did a bit about summer barbecue or something, and they had a sign that said if the grill's not clean enough for ya, go home. So I made a sign that said that above the grill. I'd make buttons with Dave's face on them, and then everyone would wear them.

Looking back on it, it's - I know it's ridiculous, but it seemed - it made perfect sense at the time, it really did.

GROSS: At the time, did you think this is what I want to do when I grow up, I want to have a late-night show?

KIMMEL: No, I know it's a much better story that way, but that is - that never crossed my mind. It really didn't. It was - I never thought there would be another late-night show. I never thought that - it never occurred to me that Johnny Carson and David Letterman would ever go off the air.

It never occurred to me, even though I knew the names of every writer on late night, it never occurred to me that you could get a job as a writer on late night. I thought those are the writers on the show and that's how it goes. And had I - had anyone ever stopped me and said, you know, maybe you should submit, you could write something, and maybe they'll hire, that's probably the path I would have taken. But it never occurred to me. I was not a bright kid.

(LAUGHTER)

GROSS: So while you were, you know, the founding president of the David Letterman club, and you had your David Letterman license plate, what were you thinking your future was going to be?

KIMMEL: I wanted to be an artist. That was my goal. I'm good at drawing, and at school that's kind of what I was known for, and it just seemed to be what I would do. Everyone of my family thought that is what I would do, and I thought that's what I would do.

But I read a Playboy magazine article. Dave was interviewed, and in that article he said he started in radio. And I loved Howard Stern. And I thought, well, that seems like it might be fun. And I was working at a clothing store in Las Vegas, and a couple days later one of the guys that worked there said, hey, you know, I work at the college radio station, KUNV in Las Vegas, and you'd be funny on the radio. Do you want to do something?

And I said, uh, yeah, I would love to do something. And I went in, had a meeting with the program director, and they had a plan for me when I got there. He said I want you to do a half-hour show on Sunday nights and make fun of local celebrities. And I thought oh, well, that's great.

And the first time I did it, I'm sure it was terrible. I don't have the tapes, unfortunately, but I loved it, and my whole family was listening. When I got home, that experience, which I'm sure you've had when you realize people are listening to you, is magical. And I was hooked in it. I mean, I loved being in a radio station. I loved radio. I just could not get enough of it.

I mean, I worked for years for free. I just loved every bit of it and just the idea of broadcasting was - it really excited me.

GROSS: Isn't that station a public station?

KIMMEL: Is it, yeah, mostly jazz.

GROSS: So Jimmy Kimmel started on public radio.

(LAUGHTER)

KIMMEL: That's right.

GROSS: Wow, that's great.

KIMMEL: And graduated to the public toilet.

(LAUGHTER)

GROSS: So you had several different personas on the air, right, over the years.

KIMMEL: I did.

GROSS: You did sports, and you did, like, morning zoo stuff, maybe?

KIMMEL: Yeah, I worked at the Q Morning Zoo in two different markets, KRQ in Tucson and Q105 in - this is how creative people in radio are. If there's a Q in it, it rhymes with zoo, and that's what we're going to call the show. But I worked at a couple of morning zoos. I did characters on the air.

GROSS: Oh, what characters did you do?

KIMMEL: I did Mike Tyson a lot. I did Snoop Dogg when Snoop eventually became a force, mostly African-American characters, which I'm sure I'd be pilloried for doing now, but Karl Malone was - is a basketball player whom I'd imitate. I did a tough, like, kind of sports-guy character, like a Brooklyn guy named Vinnie the Sports Guy my first radio job, paying radio job in Seattle. And I did that in addition to being a sidekick.

And it was fun because people didn't know we were the same guy even though our voices were identical. People didn't understand it. So every time we'd go out and do a live appearance, people would go: Where's Vinnie? Where's Vinnie? I said oh, you know, he couldn't make it. I loved that, too, because it's like you're pulling a little prank on everybody every morning.

GROSS: My guest is Jimmy Kimmel. We'll talk more after a break; this is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: It's late-night week on FRESH AIR. Let's get back to the interview I recorded with Jimmy Kimmel last January.

When you had to first figure out who are you as a late-night host, like how did you figure out who you were going to be and what your trademarks were going to be?

KIMMEL: It took a long time. One thing I did, one thing I did write is I knew that you had to have a desk, and you had to have a couch, and you had to have a band. And that I was smart enough to know, but that's where that intelligence ended. I honestly, the rest of it, I didn't know how to do it. Almost no one on our staff knew how to do it. And I just kind of figured it out just to stay alive.

I mean, really every night, every day it was like trying not to drown, just trying to get a show on the air, trying to get guests to sit in the chair that night, sometimes getting good guests, sometimes getting terrible guests, sometimes feeling very bad about myself after the show and feeling like it was a mess and occasionally feeling like, well, that went OK, maybe I could do this.

I even went through a period where I secretly hoped ABC would cancel the show because I had a lot of people relying on me, and I still do, people that work on the show, and I couldn't really quit, not that I would have, but the thought was always in my head that it would sure be great if somebody would put an end to my misery here and let me go on and do something...

GROSS: What was the misery coming from? It was too hard or too much pressure?

KIMMEL: It was relentless. It was relentless

GROSS: So it must be hard to be really stressed out because of the pressures of a new show and then come on at midnight as the relaxed midnight guy, like your day's all over, I'm going to like tell you some jokes and entertain you. Was it hard to be the relaxed, funny person you wanted to be after day after day of stress?

KIMMEL: Weirdly no because the thing about doing the show is once the show starts, everything is - the work is done. So you can relax, in a way. You can stop and enjoy it. I don't know if that's the right word to use, but you can do that because everything's done, and sometimes I walk downstairs, and I think: We have some really funny stuff tonight, and I'm looking forward to showing it to the audience.

Some nights I walk downstairs and go: All right, it's all on you, you know, to make this funny, and you might not.

(LAUGHTER)

KIMMEL: And some nights I walk out, and the audience is great, and they give me laughs where I don't deserve them, and some nights it goes the other way where you feel like something was funny, and you didn't get much response from people, and that's the nature of performing in front of a live audience, and there's nothing you could do about it.

But for me, doing the show is kind of the best part of the day.

GROSS: More or less right from the beginning of your show, you've had family involved with it, you know, your uncle, your cousin. Your old friend from I think high school is the leader of the band on your show.

KIMMEL: Yes, my best friend since I was nine years old. He lived across the street from me. And his dad is in the band, too. But my Aunt Chippy is on the show. My cousin Sal is a regular and a writer on the show. My brother is a director on the show. My fiancee is the co-head writer on the show. My cousin Mickey works in the talent department. And I've got a few other relatives not quite as close as those sprinkled throughout the show, too.

GROSS: It's often exactly the opposite for people: They get to a certain level of fame, and it's not that they cut off their family, but they're in a different world than their family.

KIMMEL: Those are smart people, those...

(LAUGHTER)

GROSS: But you've brought so much of your family into your world, and some of them are behind the scenes, some of them are in front of the camera. How did it end up that way? Why did you want to do that?

KIMMEL: Well, first I think I had to do it. The first person that I brought on the air was my Uncle Frank. My Uncle Frank was a cop in New York for 20 years. He worked as a security guard in Vegas for various celebrities like Frank Sinatra, and everyone Italian who'd come into Vegas, my Uncle Frank was their security guard at Caesar's.

And he's just - he was a funny character, and I got a kick out of him. And every once in a while, I'd have him on the radio when I was on the radio, and he was always funny. And I knew that I needed someone to talk to on the air. I knew that I needed something besides me, somebody to send to things. And instantly he fit that perfectly.

I had to convince him. In fact, he was living in New York, and the only reason that he moved out to take the job on the show was he found - he was worried about transferring his checking account. He had a specific bank at which he had a checking account, and he found out there was one branch of the bank in L.A. So he rented an apartment right near that bank, and that's what made it OK to come out.

(LAUGHTER)

GROSS: When you told your Uncle Frank that you wanted him to move out and be on camera, to be a character on your show, how did you tell him? What did you tell him?

KIMMEL: He had no idea what I was talking about. I mean he honestly had no idea what I was talking about. He was very confused. He thought he was going to be the head of security for the show, which is funny because in 20 years on the New York NYPD he arrested only six people and one was by accident.

So - and these are his retirement years. But he really didn't know what to expect, and his daughters convinced him that it was a good idea. And he just stood by the door the first night, and I think the first thing we ever shot with him was we sent him to Brooklyn with Mike Tyson to see Mike Tyson's pigeons on the rooftop. And it was a, it's an odd piece, and it was kind of sweet, and it was funny, and that's when I knew that it was going to work.

GROSS: You had him basically play a security guard.

KIMMEL: No. Well, yeah, you're right. You're right. He wasn't really doing security.

(LAUGHTER)

GROSS: OK.

KIMMEL: But he was wearing a security guard uniform.

GROSS: Yeah. Yeah. So...

KIMMEL: He thought he was doing security though, so he wasn't...

GROSS: Did he really?

(LAUGHTER)

KIMMEL: Yeah. Oh, yeah. He, you know, if something happened he would try to stop it. I mean, you know, there was a time where Andy Dick had to be dragged off the stage and there was my Uncle Frank dragging Andy Dick off the stage.

GROSS: So your Uncle Frank died in 2011 and you did a really beautiful tribute to him on the show. And I want to play an excerpt of that tribute. Here's Jimmy Kimmel.

(SOUNDBITE OF TELEVISION PROGRAM, "JIMMY KIMMEL LIVE")

(APPLAUSE)

KIMMEL: Listen, I'm going to try to do this without crying, but I'm probably going to fail. But just turn away or something, because it's embarrassing. It really is. As you may have heard, my Uncle Frank, who - already - has been a fixture on our show since our first night on the air in January of 2003, passed away over our vacation. He hated vacation, so he decided to ruin ours.

(LAUGHTER)

KIMMEL: He hated vacation because he loved to come to work. He would get here, 10, 11, 12 hours before the show started.

(LAUGHTER)

KIMMEL: The show started at - beginning at 9 PM. He'd be here by 8 AM.

(LAUGHTER)

KIMMEL: That's how he was. He was always early for everything. If he had a flight at 2, he'd get to the airport by 6 in the - if the flight was in the morning, he'd go the night before and sleep over. He'd sleep over at the airport so he didn't miss a flight.

And he wanted us to always get to the airport early too. If I had a 5 o'clock flight I'd have to lie to him and tell him the flight was at 8 because then he'd say OK, so you leave at 1? I'd say no, no. No, I'll leave at 3. OK. OK. So it's hard to believe that he is now the late Uncle Frank because he was never ever late for anything.

(LAUGHTER)

KIMMEL: He was 77 when he died, two weeks ago today. He had a few different kinds of cancer and we don't know which one got him, but one of them did. And his plan was to live to 103. He wanted to be the oldest living retired police officer in New York City, not because he wanted to set a record or be in the paper, he just wanted to stick them for another 25 years of pension checks.

(LAUGHTER)

(APPLAUSE)

GROSS: That's Jimmy Kimmel paying tribute to his Uncle Frank in 2011 after his uncle died. Was that the only time you've ever choked up like that on your show?

KIMMEL: It's happened a couple of times but I'm actually, I'm actually crying right now. It embarrasses me. I'm not sure why. I know it's a normal human reaction but there are few things more embarrassing to me than crying on television. But it was a sad night.

GROSS: Jimmy Kimmel will talk more about his Uncle Frank and other things in the second half of the show as our late-night week continues. I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. I'm Terry Gross. It's Late Night Week on FRESH AIR. Tomorrow we'll feature an interview with Jimmy Fallon, and Friday an interview with Questlove, whose band The Roots is Fallon's house band and will move with him to "The Tonight Show." Let's get back to my interview with Jimmy Kimmel. We spoke last January, just after his ABC show "Jimmy Kimmel Live" had moved from the midnight spot to 11:35.

When we left off, Kimmel was talking about his late Uncle Frank, who was a regular on the show from its first year in 2003 until his death in 2011. He'd previously worked as a New York City police officer and a security guard in Vegas. I asked what role Uncle Frank played in Kimmel's life when he was a child.

KIMMEL: He was a character. He would...

(LAUGHTER)

KIMMEL: He, this is how dinner would go. My parents never really - they didn't have friends, and my aunt and uncle didn't have friends, and my grandparents didn't have friends. They were each other's friends. So pretty much every weekend we'd go to their house and we'd have dinner, or they'd come to our house and have dinner with us. And my Uncle Frank, we'd have dinner at around 6:30, 7 'clock. My Uncle Frank would clear all the plates off the table, and then he would announce that he had to go to bed. And so he'd go to his bedroom. He'd say goodnight to everyone, and then, once an hour until about midnight, he'd come out of his bedroom in pajamas and go, Chippy, did you pay the water bill? She'd go, yeah, Frank.

So, he really wasn't going to bed. He was just trying to get away from everyone, and when he cleared the plate, it wasn't because he wanted the house to be neat. He just wanted us all to go home. He really wanted - wherever he was, he was ready to leave, and wherever he was headed, he was ready to go there. And I think it was anxiety more than anything, but it tickled us and we, you know, of course, we'd goofed on him all the time and we'd ask him over and over again what time he's leaving for the airport. The story about the airport, I mean, there were many times where he slept over at the airport and it's crazy but that's just how he was. He's a very odd guy but always very nice and always very funny and just a good, solid guy.

GROSS: I read that there was a period when you were young when you would actually videotape family fights. And I'm thinking what a weird thing to do and how weird it was that your family allowed you to even do that. So...

KIMMEL: Even weirder, I didn't have a video camera. I'd make cassette tapes of the family, not just fights.

GROSS: Oh, it was like audio, audio tapes?

KIMMEL: Yeah, audio tapes. And not just fights, everything. I just tape a whole dinner and then my cousin Sal, we'd grab the tape and then we'd memorize it. We've listened back to it over and over again.

(LAUGHTER)

KIMMEL: I remember a particular passage, as my Uncle Frank was trying to get ketchup out of the ketchup bottle and he's shaking it. And he was, he would give up on things almost immediately. So he's shaking the ketchup and he goes to his wife, my Aunt Chippy, Chip, how do pour this? She goes Frank, you got to shake it. And he's shaking it. Shake it, Frank. Frank, Frank you got the - Frank, you got to open, the cap is on, Frank. You got to open the bottle before it will goddamn pour out. And then she goes on a rant. He's so stupid it's pathetic. He'll never invent the airplane. He'll never invent the light bulb. He's lucky if he knows how to turn one on.

(LAUGHTER)

KIMMEL: He'll never invent the airplane.

GROSS: So you in your cousin Sal would record this and then memorize the lines and do it as a routine for each other?

KIMMEL: Not only that, we had a book of quotes from my Aunt Chippy that she never said.

(LAUGHTER)

KIMMEL: So we'd make things up that we imagined her saying. She's very - especially when she gets mad, she's very creative. Her analogies are ridiculous but also very imaginative. And so we'd write - we have, in fact, I still have it. It's like a binder, a three-ring binder and we'd write things down that we think Aunt Chippy might have said.

GROSS: So Sal works on your show.

KIMMEL: Yes.

GROSS: I mean he does writing. He appears in sketches. So do you and he - have you and he thought up things for the family to do on the show?

KIMMEL: Oh, yes, all the time. I mean, we're always coming up with things, especially when I have a family-related prank or some kind of a mission to send them on; I always consult with Sal because he knows which buttons to push.

GROSS: So give us an example of one of the things you cooked up with Sal?

KIMMEL: Well, we decided - I was driving with my Aunt Chippy, and she was complaining about people who come to this country and don't learn to speak English, and it was ridiculous. My grandparents came from Italy and they learned how to speak English. And she just goes on this long, xenophobic rant, and Sal and I looked at each other and we realized that this was a weakness and this was something that we could, a vulnerability we could expose. So I put that in my memory bank.

And something I've always wanted to do is paint somebody's house while they're away at work. So, while my Aunt Chippy was out at work, we had a bunch of actors pretending to be painters - also pretending that they don't speak any English - paint her house orange and green.

(LAUGHTER)

KIMMEL: And she comes home from work and her house is bright orange and green, and she starts yelling at the workers, demanding to know what's going on. And none of them speak English, which makes her madder and madder, and then there's a guy on the roof who hands her a beer and she goes crazy and throws it at him. They're painting the trees in her yard. It was probably my finest hour.

GROSS: And was this a hidden camera or did she know that she was being filmed?

KIMMEL: Yeah, it was a hidden camera prank that we did.

GROSS: And she was okay for you putting this on the air?

KIMMEL: Yeah, she was OK 'cause at the end of, after the prank was over we repainted her - her house hadn't been painted in 35 years, so we repainted her house to its original condition.

GROSS: But the...

She was pretty mad for an hour or so.

I, you know, I think it's so interesting that you've been able to take things about your family that might horrify people about their own family.

(LAUGHTER)

GROSS: You know, it's so awful when someone who you know well or someone in your family says something like racist or xenophobic.

KIMMEL: Yeah.

GROSS: It's like oh, like please don't. Don't. And you managed to like make a funny comment on xenophobia with your own family by...

KIMMEL: Well, I think that's the way to go. I think that's the way to - I think that's the way they did it on "All In the Family." And I think with my Aunt Chippy, I think people get old and this happens.

I'm from a very liberal family, very tolerant family, but there are little things that, you know, that I don't know. She's from New York. She's from Brooklyn. She's Italian. She's old and she's cantankerous. And these are the sorts of things that bother her for some reason.

GROSS: My guest is Jimmy Kimmel. We'll talk more after a break. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: It's late-night week on FRESH AIR. Let's get back to the interview I recorded Jimmy Kimmel last January.

You do a lot of pranking on your show and we talked a little earlier about that you started your career on radio. I know you were fired from some of your radio jobs so I don't know why. Did you do pranks on the radio and did that get you fired?

KIMMEL: Yeah. I did - the pranks didn't get me fired. But I love pranks, I really do. I don't know if it means something's wrong with me. I've told the story of my mother, when my sister and I were little, she would lay on the ground and pretend to be dead until we cried.

GROSS: Nice. Very nice.

KIMMEL: She got a real kick out of this.

(LAUGHTER)

KIMMEL: And it's one of the things she - I don't think she realized it was sadistic until I spoke about it in front of other people and they went, oh my god.

(LAUGHTER)

KIMMEL: And it's funny because when I talk about it with my cousins they're like, yeah, my mother did that too.

(LAUGHTER)

KIMMEL: It's a family tradition, I guess. But something about seeing people put in situations where they get mad or flustered, there's something about that that makes me laugh uncontrollably. And I know, you know, I know sometimes people say well, don't you think it's mean? And maybe it is but I just can't help myself. I really can't.

GROSS: Yeah. Because you did a prank where you asked parents to prank their kids and tell their kids that they'd stolen - that they'd eaten all of the kids' Halloween candy.

KIMMEL: Yes. Yes.

GROSS: And then put that on YouTube and to send it to you. So the kids, I mean, the kids are just, they're, like, weeping. I mean, they are, like, weeping they are so upset. And they're so angry. And the kids don't understand what a prank is. They don't understand what a practical joke is.

KIMMEL: They do now.

GROSS: They do...

(LAUGHTER)

GROSS: And so it created this, like, big controversy. Like is Jimmy Kimmel being cruel to children by having parents pull these pranks on them? So is Jimmy Kimmel cruel to children?

KIMMEL: Well, yeah, probably. But, no. No, not really. I mean, kids cry like 40 times a day.

(LAUGHTER)

KIMMEL: I mean, you know, people look at it and they try to equate it somehow to - you know, if I made an adult cry I would say, oh, my God, this is terrible. I'd really be upset, but, you know, kids cry constantly and I think it's - I don't know, there's something very cute about it, and I also think that these kids will treasure that video when they're older and when they look back on it.

And you know what? Nobody loves a prank more...

GROSS: No, no.

KIMMEL: ...than a little kid.

GROSS: The kids are going to show the video to their therapists.

KIMMEL: Yeah. Maybe so.

(LAUGHTER)

GROSS: And they're going to talk about how cruel you are to children.

KIMMEL: A lot of people seem to like it, though. I think it has like 38 million views on YouTube.

GROSS: So earlier we were talking about how much you love David Letterman and what an inspiration he was to you in high school and how obsessed you were with him. Did you personally break the news to him when you found out that you were going to be moved to 11:30? Did he hear that first from you?

KIMMEL: No. I try not to bother him, and I never contact him. Occasionally, I'll send him a thank-you note or a little note in writing. But I feel like I know Dave pretty well even though I don't know Dave very well, and I get the idea that he's not looking for a lot of interaction. But he did call me and congratulate me and wish me luck on it. He understands how important he is to me, and he's been very nice.

And you know how they say you don't want to meet your idols? I've been very, very lucky because the people that I idolize have been very kind to me. And I'm glad, because it really would be upsetting if they weren't.

GROSS: Did Leno wish you luck? Because you and he had kind of a feud, you know, especially when you were on his 10 o'clock show.

KIMMEL: Well, he didn't reach out and wish me luck, specifically, but I'm sure he thinks good thoughts.

(LAUGHTER)

GROSS: OK. So when you were on his show back when he was on the 10 o'clock show...

KIMMEL: Yes.

GROSS: ...and he was doing a feature called 10 at 10 in which he'd ask a guest 10 questions. When he asked you the 10 questions, you would answer the question and then get in a little, like, jab at him. Because this was right after his show at 10 o'clock was failing. That show was going to be canceled and he was going to move back to the "Tonight Show" bumping Conan O'Brien from that slot.

And you were pretty angry about that, and you made that clear in a very funny way in your answers to his questions. In fact, I'm going to just play a little bit of that.

(SOUNDBITE OF TV SHOW, "THE JAY LENO SHOW")

JAY LENO: Number four, if you got to interview anyone in the world who would it be?

KIMMEL: You and Conan together.

LENO: Oh. That's good.

KIMMEL: I would like to have the two of you...

(APPLAUSE)

KIMMEL: And if Conan won't do it, I'd like just you - in fact, I'd like to do 12 at 12 with you tomorrow night.

LENO: Really?

KIMMEL: If you would be willing to do that. Because I have a lot of questions to ask you...

LENO: Yeah.

KIMMEL: ...about this whole thing. Well, I don't think people care about what I have to say.

LENO: Yeah. Yeah. I agree with that.

KIMMEL: They'd much rather hear what's going on in your life.

LENO: Yeah. Yeah. Tomorrow night at - aw, tomorrow night's bad for me. All right. Let's move on.

KIMMEL: Oh, it is bad?

LENO: Number five. You're known for pranks. What's the best prank you ever pulled?

KIMMEL: Well, when my Aunt Chippy was at work I painted her house orange and green once. And she was not happy.

LENO: Really?

KIMMEL: The whole outside of the house was - yeah. But the best - I think the best prank I ever pulled was I told a guy - I told a guy that five years from now I'm going to give you my show, and then when the five years came, I gave it to him and then I took it back almost instantly.

LENO: Wow. Wow.

KIMMEL: It was a loan.

(APPLAUSE)

LENO: Yeah, yeah.

KIMMEL: He still will not speak to me.

LENO: Very good prank. Very good prank.

KIMMEL: I think he works at Fox or something now.

LENO: Yeah. Yeah. I gotcha. All right. Number six. Ever order anything off the TV?

KIMMEL: Like NBC ordered your show off the TV?

LENO: Yeah, yeah. No, no, no. No.

AUDIENCE: Woo.

GROSS: So that was Jimmy Kimmel, my guest Jimmy Kimmel, on Jay Leno's 10 o'clock show. Any regrets about doing that?

KIMMEL: No. I don't have any regrets. I mean, I agreed to go on that show and I assumed that we would talk about the elephant in the room, which was that Jay was going to be replacing Conan. And in fact, the reason I was on the show was because I'd imitated Jay, as a result of that story, on my show.

But when the producer called me and he went through the questions, none of them were about what people wanted to hear about. And I said, well, we can't do this. We can't just have a bunch of generic questions about nothing when people want to hear what we're going to say about this move.

And they said, oh, yeah. OK. OK. Yeah, well, OK. But then the time we get on the air none of the questions are about the move back to "Late Night." And I said you know what? I'm not going to do this. I can't do this. And so I decided to make every question, no matter how far removed it was from the topic, about that topic.

GROSS: So I have to ask you about Matt Damon.

KIMMEL: Yes.

GROSS: He's been a recurring character on the show because you end your shows by saying...

KIMMEL: Apologies to Matt Damon. We ran out of time.

GROSS: Yes. And he's been on a couple of sketches, most notably the video that went viral that he and Sarah Silverman did. How did he become a running gag on your show? Are you friends?

KIMMEL: It was - no, we weren't. Well, we are now, but at the time he was just - we had a bad show. And the guests were bad, and I was feeling pretty bad about myself at the end of the program. And I decided to say, for the amusement of one of our producers who was standing next to me, I said and I want to apologize to Matt Damon. We ran out of time.

Meanwhile, we'd had a couple of reality stars or something on the show that night. And he got a kick out of it, the producer, and so I just started doing it every night to amuse him. And Matt Damon was just the first name that popped into my head. I just was trying to think of an A-list star, and somebody we absolutely would not bump if he was on the show.

And it just kind of continued from there. And then, you know, I didn't plan to do it forever but he - people started asking him about it and he got a kick out of it. And we heard from his publicist that he liked it and that we should keep doing it. And so we kept doing it.

And it became - you know, and then they did the video and there's been a lot of back and forth. And it's been a lot of fun. It really has - the legs on this bit are unbelievable to me. I mean, people laugh every time I say it. And you don't get, you know, repeating the same joke every single night, you'd think eventually people would get tired of it, but they don't.

GROSS: Jimmy Kimmel, thank you so much for being on our show. I wish you all the best of luck with your new time. And thank you.

KIMMEL: Thank you, Terry. It was a lot of fun talking to you. I listen to you all the time and I appreciate being asked to be a part of the show. I feel like a real person now.

(LAUGHTER)

GROSS: Thank you so much for saying that. I want you to leave us with one thing. You did a series asking celebrities - you say that Twitter is the most popular way of insulting celebrities.

KIMMEL: Yes.

GROSS: So - and you had a series of celebrities reading insulting tweets about them. What is the most wonderfully insulting tweet that you remember about you?

KIMMEL: Oh.

GROSS: That you can say on the radio. Yeah.

KIMMEL: Let's see. Yeah. They are almost all - there are very, very insulting - people are so cruel. And I do read every one of these tweets, so if you have something terrible to say about me, trust that it is going to hit home.

(LAUGHTER)

KIMMEL: You know, they range from my appearance, to my abilities, to just general insults about things that no normal person would ever say if you were to meet them face to face. Boy, I wish I could think of one, specifically. But maybe the most insulting thing is when they tell you you look just like their brother and then include a picture of their brother and their brother's a big fat slob.

(LAUGHTER)

KIMMEL: It's a compliment - those are the worst.

GROSS: Well, Jimmy Kimmel, thank you again. Be well and thanks.

KIMMEL: Thank you. Take care.

GROSS: My interview with Jimmy Kimmel was recorded last January. Here's an excerpt of Kimmel's feature "Celebrities Read Mean Tweets."

(SOUNDBITE OF TV SHOW, "JIMMY KIMMEL LIVE")

SELENA GOMEZ: Selena Gomez is on the radio right now. Is there a volume lower than mute?

Sorry.

LARRY KING: I saw Larry King at dinner but it might've been just a run-of-the-mill goblin.

DR. PHIL MCGRAW: Dr. Phil, why don't you shut the (bleep) up, you bald-headed big-mouthed hillbilly?

SIMON COWELL: Simon Cowell, you, my friend, are a (beep).

JESSICA BIEL: My Asian orthodontist says Jessica Biel has horse teeth. (sighs like a horse)

HAYDEN PANETTIER E: No one else finds Hayden Panettiere intolerable. Is that a question?

ANDERSON COOPER: I'm not being mean but why does Anderson Cooper remind me of dinosaurs? (Beep) you.

ERIC STONESTREET: Eric Stonestreet, why so awkward and yelly? I'm not awkward and yelly!

BRYAN CRANSTON: "Malcom in the Middle"? More like "Mushy in the Middle." Lose some weight, Heisenberg. I've had a good chuckle out of that one. I'm coming after you, TX Griz.

GROSS: And that last person we heard from was Bryan Cranston. Our Late Night series continues through the week. Each day the latest interview from the series will be added to our Late Night theme page and available for download on our website freshair.npr.org. Coming up, David Edelstein reviews the new film "Short-Term 12" which won the Grand Jury and Audience Awards at this year's South by Southwest film festival. This is FRESH AIR. Transcript provided by NPR, Copyright NPR.