Last week, The A.V. Club spoke with talk-show host Conan O'Brien about his current career: Hosting the Emmys, planning to take over The Tonight Show, and taking his own show on the road. In part two of our interview, O'Brien digs into his past, discussing how he got where he is, how many crappy jobs he had to take along the way, and what it's like being the hired entertainer at a 7-year-old's birthday party.

The A.V. Club: You were the president of The Harvard Lampoon twice. What was the Conan O'Brien reign like? Did you rule with an iron fist?


Conan O'Brien: I was like [Romanian dictator Nicolae] Ceausescu. I was malevolent and arbitrary. It was like when Stalin, toward the end of his reign, just turned on people for no reason. So there was that quality to my rule: I was the idiot king. When a king dies suddenly of an expected illness, and a 16-year-old is elevated to the throne and immediately declares purges of everyone around him—that was my reign at the Lampoon.

AVC: Considering The Harvard Lampoon's reputation, it seems like you should have gotten a television contract along with your diploma.

COB: I was shocked when that didn't happen.

AVC: Didn't you have offers? Weren't there people paying attention to your writing and career?


COB: No one was that interested at the time. That thing was just starting to happen, that pre-professional aspect to the Lampoon that later became the stereotype. I mean, there were a lot of people in my class who didn't go into television. My Lampoon friend Greg Daniels [later of Simpsons, King Of The Hill, and The Office fame. —ed.] and I said, "Let's give this a shot, let's go out to L.A. and try." So we went. The first job we got was on Not Necessarily The News, which was an HBO show. It was a good job for us, because it got us into the union. And it got us some experience. We were locked in a fluorescent room. We could've been accountants, because they locked us in a room and said, "Write visual jokes. Write gags." We wrote a ton of jokes that they could use to accompany footage. That was actually a pretty good exercise, because all these years later, I still feel like for a couple of years at the beginning of my career, my job was just to think about jokes and visual humor. And I was literally chained to a desk doing it. It was a good way to do it.

AVC: Did you come up with Sniglets during your time at Not Necessarily The News?

COB: No, that was Rich Hall. My thing that I always wanted to do was have Rich Hall do Sniglets, but use real words. [Adopts sinister voice.] "The act of taking someone's life against their will is called 'murder.'" Like, make them really, really dark.


AVC: That would make people think.

COB: Of course, that wouldn't have sold any of the Sniglet books.

AVC: Early in your career, you appeared in corporate infomercials. Do any of them stand out?


COB: I did an infomercial for the Musical Instruments Vendors Association Of America. That's not their actual title, but I don't remember what it was. They had a handsome-headed man who was there to narrate it. He'd say, "Don't be the know-it-all salesman when you're selling a musical instrument, like this guy!" They used me because I could improvise, which meant I was a comedy writer who could perform, which meant they didn't have to pay a writer. They hired me and it was not scale, it was kind of an illegal job. And then I'd be the know-it-all who alienates customers. I'd say "Oh, you don't want that bass. That has three-amp-per-unit sensor round on the third pickup!" Just babbling, and the customer would shrug very broadly and say, "This guy is ridiculous. You're giving me too much information!" And then he would storm out of the office. And then they'd say "You should be more like this guy!" and I would be more accommodating and listen more than talk. I didn't know anything. They told me I'd have to bring my own makeup. I didn't even know what that was. I went to a mall and went to the women's makeup counter and bought some stuff. And drove my $300 navy-blue Isuzu Opal to some part of the Valley that took an hour and a half to get to, and sat in a parking lot in 100? heat, putting this glop on my face. I walked in and I looked like a melting candle. I looked like Jack Klugman in the last season of Quincy. It wasn't good. So there you have it. We all do things. I was a male whore for a while.

AVC: You also were an entertainer at a 7-year-old's birthday party at least once. Care to elaborate on that?

COB: It was horrible. Bombed. Completely bombed. Those kids were assholes. They didn't know quality when they saw it. A friend of mine and I who was a fellow improviser, a guy I knew at the Groundlings Theatre, he came to me, he said, "Hey, I got this gig to entertain at a kid's party, and they're paying, and it's cash, man." It sounded like a drug deal. "It's cash, and they want us to go there. We got to work fast." So we went there and we had guitars and pranced around. It was classic. The kids were like Easter Island statues. They just stared at us. I think the mom who had hired us was just like, "What is this crap?" We were doing weird characters and stuff. I think we got paid, but it was one of those things where they pay you grudgingly. You almost wish they didn't pay you. They really despise you. Not good. People say all experience is good—not true. That was a complete waste of time, and humiliating. If I could get into a time machine, I wouldn't use it to save Abraham Lincoln's wife, or cure polio a little earlier. I'd use it to wipe out that birthday.


AVC: Speaking of humiliation, during all that time, you also worked at Wilsons House Of Suede And Leather.

COB: What was worse, I was mostly working a desk job at Wilsons. So it wasn't even getting to handle the amazing suede merchandise. I was mostly at a desk. I was the male secretary to this hot woman who used to come to work wearing a miniskirt and white cowboy boots. And I was her assistant. It was like a bad porno. "Conan, can you come in here for a minute? I need you to help me clean out my pipes," or something. Never happened. I used to play guitar music just to see if I could get her in the mood. But no, nothing ever happened

AVC: You were fired from Not Necessarily The News, right?

COB: Not really. It makes a better story to say you were fired. I think they downsized. HBO cut their budget, so they had to lose five writers or something. They kept the people with the most seniority, and let the rest of us go. It was pretty amicable. "Fired" has a better ring to it. It's a better story if I had a lot of hardships. "They fired my ass. I was embezzling from the company."


AVC: From there, you were one of the writers and producer of the short-lived Wilton North Report. Paul Krassner wrote an article about it.

COB: Paul Krassner was there. The whole time we were trying to make the show, he was saying, "This can't work." What was interesting about that show—there's no better experience in television than to work on a flop. Because you learn all these amazing things that help you later on. It's being a part of a horrible shipwreck that makes you a better sailor, provided you stay in the business. I learned a lot.

When Late Night first came on the air and was having trouble, people were saying "We're going under, we're going to get cancelled." I remember thinking, "I've been on one of those, and this just doesn't feel like that. Our show gets better every day, and that show didn't." That show sort of felt like everything went wrong. It had this feel to it where I didn't even know what we were going to do next week. Whereas on Late Night, at the beginning, we always had a lot of ideas. We always felt we had a good show for the next day. We never had that feeling of "Omigod, I'm lost." It was just convincing the rest of America or NBC that we knew what we were doing.



AVC: The Wilton North Report did seem like an attempt to do an entirely new kind of show.

COB: I think the problem with that show is, the producer hired the writers first, and the last thing he did was go and look for the talent. It was done backward. They had all these auditions for the talent: Rosie O'Donnell came in, and Ellen DeGeneres, and the producers were like, "Nope, nope, nope." And they hired these two San Diego DJs who were very nice guys, but it felt like the writers were already hired, and the show kind of had a sensibility where the writers and performers didn't match. It was great, because I was so young, I was just out of college. I experienced firsthand all these things that seemed kind of logical to me at the time. But later on, I realized it was the completely wrong way to do it. Like it or not, the performers are in charge, and it's their voice, and it's amplifying what's inside them. It's an extension of who they are. That has to be the hub. On that show, the performers were like an afterthought. "We got the writers, we got the producers, we're starting to think of bits, and then at the last minute, let's get some performers." It felt like, "Well, that can't work." I learned a lot there. Because it was such a chaotic show, I got to do bits on The Wilton North Report. I remember feeling like, "I kind of like this. I'm not that good at it yet, but something about it feels right." And not in an "I've-gone-insane-and-I-have-a-huge-ego" kind of way, because I never really did.


AVC: In the Krassner piece, the early conception of it was "The Today Show meets Siskel & Ebert."

COB: If you'd asked anybody on the show what it was, nobody could tell you. "It's Harry And The Hendersons meets Citizen Kane." "What? What is it?" "It's a show where they sell electronics." "But I'm still confused. What is it?" "It's a show where chocolate is manufactured and sold to the Belgians." Every day, you might hear something different.

The piece that I was really proud of… Are you familiar with Iron Eyes Cody, the weeping Indian that did the "Don't litter" commercial from the early '70s? After he passed away, they found out he was Italian. I did a piece on that show where I found him and I did a series of shorts with him. In one, he's coming out of an ice-cream parlor, and a scoop falls off his ice-cream cone and lands on his moccasin. He looks up and slowly does the tear with the same dramatic music. I had him review movies. Like, "Here he is with his review of the Barbra Streisand movie Nuts."


At the time, the person I wanted to emulate was Chris Elliott. I used to look at Chris Elliott and think, "That guy's doing what I want to do. He's a writer who has funny ideas, but he gets to go on TV and present them himself." I went on the program to present my shorts of these movies I made. It seemed to go over pretty well. I was so excited, and I flew home the next day because it was Christmas break. My flight was cancelled because I was taking a cheap airline, and I got to my parents' home at 10 a.m. on Christmas. I walked in, and no one mentioned my appearance on TV. And I had told them to check it out. I was crushed. No one mentioned it. I was depressed and thought "They really hated it that much?" I worked up the nerve to say, "So, did anybody see what I did on national TV last night?" They said "No, we didn't see it, because they cancelled that show last night in our market." Cities left and right were saying "We're not showing this shit anymore."

It sounds corny, but I learned a lot. I got knocked around a bit. That's kind of what I'm telling people who work here. One of my first jobs in show business was as an intern on [the charity comedy-concert series] Comic Relief. Raising money for homeless people with comedy always seems funny to me. "We'll have a laugh and help cure tuberculosis." But whatever. My first job was to get coffee for Estelle Getty. "Whatever Estelle Getty needs, you're it, boy." So that was my first job in show business, right out of college. Estelle Getty tearing me a new asshole.

AVC: Do you have a lot of Estelle Getty anecdotes?

COB: The coffee would be cold, and she'd throw it in my face. She carried a box-cutter and cut me with it. There's more where that comes from. When people here ask for advice, a lot of them ask, "How can I do what you're doing?" Well, don't be afraid to take anything that comes your way, anything that puts you in the proximity of the business. If it means your job is finding a Corolla for Adam Carolla, do it. At least it gets you in the general vicinity of where they're making something.


AVC: From there, you were a writer for Saturday Night Live. What was the atmosphere there?

COB: I found it a little nerve-wracking there. I think it was more nerve-wracking to be a writer at SNL than it is to be the host of my own television show. I'd be hard on myself, and I always wanted to have a good idea every week that would get on the air. It's very difficult. I watch SNL, and they have trouble coming up with endings for sketches. I had that same problem. A really good sketch is a classic piece of work, and the idea that you're supposed to have one of those 20 times a year is absurd. It's harder than it looks. It's funny, because every now and then, they show the old SNL on the E! channel, or Comedy Central. Every now and then, I'll be passing the interns' room—they have a conference room where all the interns hang out—and they'll be watching a SNL from my era. I'll pass and peek in the door, and it's one of my sketches, and it's been so long, I forgot how it ends. It's okay. The interns are laughing. It's a pretty funny sketch, and I start to think, "I wonder if I was able to come up with an ending." And then I watch and, nope. Pretty lame ending, just sort of trailed off, and then they cut to G.E. Smith wailing on his guitar.


AVC: Someone who was really good at writing skit endings would probably be the most sought-after comedy writer in the world.


COB: One of the reasons why I love the format I'm in now is, it's a little more of the Monty Python/Mr. Show formula. It's too much of an expectation that sketches have a big ending. On our show, we can show you something for as long as it's funny, then stop. Every now and then, if a sketch doesn't have an ending or I really hate the ending, I'll say "We're not doing it. I'll talk to Ashanti for another hour. I'll just wrestle Will Ferrell for another act." It gives us another day to either kill that sketch, or come up with an ending that works. On SNL, it's harder to do that. If I'm not happy with what we have, I can bunt, or get on base, or draw a walk. There, they have to hit a home run each time. It's a difficult format, especially today, when everything is scrutinized. In our culture, something is either great, or it sucks. I think that's what difficult.

AVC: When you were at SNL, one of your more famous skits was the nude-beach skit.

COB: It was Robert Smigel's idea, and I helped with it. Over the years, it's gotten credited to me—there were others that were more mine, but that one was Robert Smigel's initial idea.


AVC: Did you think you'd get away with saying "penis" 43 times? What was the thinking behind that?

COB: You know, you're in your 20s, you're obsessed with your penis. We thought, "Let's try it." I think eventually it got on the air with Matthew Broderick. One of the good things about that sketch is, we wrote it, and it didn't get on the air, and we were depressed about that, and then there was a writer's strike. That's when we decided to go to Chicago and put on some of the sketches we couldn't get on the air. That's when we did this show called Happy Happy Good Show. It was a big thing for me, because it was that show that made me realize, "I'm not getting paid anything. I'm living on the floor of Jeff Garlin's apartment. I have no money. I'm miserably hot"—because it was the hottest summer in Chicago history—"and yet I'd rather do this than do anything else." It really got me into the idea of, "Screw it, let's perform."

AVC: When you were at SNL, did you nurse ambitions of performing on the show?

COB: I didn't, really. I was always looking for the context where I was funny as a performer. I was smart enough to know what I wasn't. I never once stood on the sidelines and watched Jon Lovitz and Dana Carvey and thought, "Dammit, why them and not me?" Because they had this skill-set which was very different from mine. And I thought, "So much of my sense of humor and my comedy really comes out of me being myself." Those guys—Phil Hartman could become other people. And I thought, "That's not really what I do so much. I can be funny as myself." At that same time, when I was writing for SNL, I was watching David Letterman and thinking "I'm not the same as him. I'm really a different person." And I remember feeling kind of envious, wanting something where I could be myself, yet tell some jokes and present weird comedy. I remember that having a lot of appeal to me. I didn't have the temerity to think I could be Letterman. I was never wildly self-confident, but I remember having this burning feeling that was treated later. Something about what he was doing rang some sort of bell with me. I didn't know what it was, but later on, I figured it out.


AVC: You left SNL to create the pilot for Lookwell, right?

COB: No, I sorta did Lookwell during a hiatus from SNL. I did Lookwell with Robert Smigel. That didn't go, and I was really depressed about that. I went through a bad breakup around the same time. And I just thought, "You know what? I'm fried on SNL." So I quit SNL with no job prospects—this is the kind of thing that infuriates people—and literally three weeks later, I got a call from The Simpsons. They had heard I was cast adrift and that I was literally walking around New York reading books, sitting on park benches, and living off hot dogs.

AVC: And screaming at passersby to stop stealing your thoughts.

COB: I had an aluminum-foil helmet, and my pants around my ankles on the subway. The Simpsons was still early in its run. They hadn't hired anyone new. It was still the original team. So they said, "Look, we hear you're available, do you want to come work at The Simpsons?" It seemed perfect. The Simpsons were like the dream team. They had people like George Meyer, Jon Vitti, Jeff Martin, Mike Reiss, and Al Jean. I could rattle off all the names. I knew all these people. The idea of being in a room with them was really intimidating, but I wanted in on that. It was great. I jumped on a plane, went out to L.A., and found an apartment in a day, and I was a Simpsons writer.


AVC: Greg Daniels, the co-creator of The Office and King Of The Hill, was a friend of yours from Harvard. Was he on the show at that point?

COB: No, he and I overlapped by one day. I was at The Simpsons for what, two seasons and change, and I left to do Late Night. I swear, my last day at The Simpsons was a Wednesday, and Greg came in for part of that day. So it was like two trains passing in the night. I was off to do my thing, and he went to The Simpsons.

AVC: Was writing for The Simpsons like being back at the Harvard Lampoon?

COB: Not really, because it's very different. A job is a job. There's a reason it's called a job. So many people come up to me and say "It must be a dream to work at The Simpsons." Well, it was a great job. That room was one of the funniest rooms I've ever been in. It's terrific in a lot of ways. But you're still pulling an oar to make something move forward, and that's a long day. There were no vacations at The Simpsons that I can recall. You're in a poorly ventilated room with horrific furniture, worse than any furniture that had been in my dorm room. In my dorm room, we had, like everyone else, found furniture. Like, "Look at this thing on the sidewalk! It looks pretty good!" When you're there, it's really fun, but when it's 10 o' clock at night and you just want to go home, but you can't until you figure out what Marge says after Homer shoves the plutonium rod through his ear, and you've got to come up with that next line: "Oh, Homey!" It gets kind of grim. I'm kinda hyperkinetic. I like to move, and I like to keep busy. I can't sit still for long. That was the hardest thing for me as a comedy writer. On a show like that, it was tough to sit still and come up with stuff. If the Simpsons writing staff were The Dick Van Dyke Show, I was Morey Amsterdam. I was constantly standing on the edge of the couch. I was constantly hanging from the ceiling, I was doing anything I could think of to make the writers laugh, and sort of acting like a chimp.


AVC: Which isn't bad preparation for getting your own show.

COB: No. When the whole concept of me even auditioning for Late Night came up, I remember John Swartzwelder, who is one of the greatest Simpsons writers of all time… He doesn't say much. He's a man of few words, but when he says something, it has a lot of meaning. He's one of those guys. Someone brought up the possibility of me auditioning for this show, and he looked at me for a while and said, "I'd watch your show." He was sort of saying, "I think I've been watching you do a show in here for two years."

AVC: In the Simpsons DVD commentaries, you're talked about in revered terms. It seems like you were always on. Is that a curse as well as a gift?


COB: Ask Robin Williams. Ask Dane Cook. Yunno, it's weird, but I don't know. I've been this way since I was a kid. I said something about this in an interview years ago, and my dad called me up and said, "That was so perfectly true about you." Unfortunately, the quote was, "I'm making a living off of something that should be treated." I had mixed feelings that my dad thought that that was absolutely the best, most true thing I ever said about myself. I feel like when I'm gone, if they should do some sort of autopsy, they'll find that the gland that helps keep you still is withered or completely destroyed.

AVC: One of the great things about show business is that so many times, horrible personality flaws become positive things.

COB: The other thing that's funny is, after the show, I come upstairs and do a show for the writers. It's kind of crazy. I come upstairs and I pick up my guitar. I love the writers' room. I'll walk in there and start singing improvised songs about how one of the writers is a pedophile, and wrestle with people, and throw out really weird ideas. So I clearly found the best use of me. For lack of a better way of looking at it, if I existed 200 years ago, all the other farmers in my community would be like, "That guy is worthless! He's sitting on a rock, jumping up like a frog, coming up with weird concepts and ideas, making faces, and combing his hair into a giant pastry." It's a good thing I was born in this century, when superfluous television seems to be part of the economy.


For part one of this interview, click here.