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Happy 20th Anniversary, Conan: O’Brien on 8 Iconic Early Late Night Bits

Twenty years ago tomorrow, the cold open to the very first episode of NBC's Late Night With Conan O'Brien ended with a sunny, smiling O'Brien stepping on a chair and matter-of-factly slipping a noose around his neck. The literal gallows humor was appropriate: Prior to that first episode, TV-industry insiders had almost universally been predicting that the former writer for The Simpsons and Saturday Night Live would fall flat on his face, joining Chevy Chase and Alan Thicke in the Failed-Talk-Show-Host Hall of Shame. Here's how bad O'Brien's pre-launch buzz was: Entertainment Weekly found a way to trash his version of Late Night before it even premiered. After sneaking a reporter into one of O'Brien's test shows, the magazine published a merciless critique of that outing under the headline "Conan the Unbearable?" that complained, "Uncomfortably shifting from side to side, O'Brien got the dry run off to a rotten start by feigning mock rage," before the writer proceeded to dismiss everything from sidekick Andy Richter ("a cross between Chris Farley and Andy Rooney") to the show's set ("a Lucky Charms motif"). Two decades later, the words still make a reader wince uncomfortably.

Of course, everything turned out fine for O'Brien. He's about to start his fourth year as host of TBS's Conan, with TBS recently renewing the show through 2015. And while there was that brief period of time in 2009 when NBC pretended to turn over The Tonight Show to O'Brien, the bulk of his NBC tenure turned out to be a commercial and critical success. Under his watch, Late Night became known as the home to some of TV's sharpest, most absurdist humor. His show, with the help of Andy Richter, producer Jeff Ross, executive producer Lorne Michaels, and a first-season writers' room that included Louis C.K., Robert Smigel, Dino Stamatopoulos, and Bob Odenkirk, would go on to win a half-dozen Writers Guild of America awards for its writing and an Emmy in 2007.

To mark the twentieth anniversary of O'Brien's late-night career, Vulture decided to focus on one of the main reasons Late Night With Conan O'Brien ended up thriving: The almost countless parade of recurring characters and bits the show cranked out during its run — particularly in the early years. Some would become iconic, spawning books and merchandise: Triumph the Insult Comic Dog, If They Mated, the Masturbating Bear. But there were literally hundreds of other recurring segments O'Brien turned to over the years, so many that even he has trouble keeping track of them all. "The other day [Conan head writer Mike] Sweeney was showing me a list of all the comedy bits we've done over the last twenty years, and I was sort of blown away," O'Brien told us earlier this week during a phone chat. "The thing I'm most proud of is the incredibly varied types of comedy — how many ideas — were packed into those shows. Just us talking about it, you can't even scratch the surface."

And yet, scratch we did: Vulture identified eight stand-out bits from the first five years of Late Night, and O'Brien generously gave up an hour of his time to talk about how those segments came together and why he thinks they worked. It also turned out eight wasn't enough for O'Brien. Toward the end of our conversation, he brought up one more bit from back in the day: an obscure character he absolutely ... hates.

NEW CHARACTERS
A catchall segment in which Conan introduced absurd new additions to the Late Night repertoire of random characters.

"That was very left brain. It was a safe way that we could think of absolute nonsense. So many of the best things are born from desperation. You need to fill an hour a day, and we used to obsessively pride ourselves on doing more comedy than any other show. Just punching out more comedy. So we would throw a million things up against a wall and see what stuck. Whenever someone thought, "Oh, this might work," then we would do it.

"There was a character Brian McCann used to do called 'Mick Ferguson, the Man Who's Awfully Proud of His Bulletproof Legs' that I loved. Brian is such a great performer, and he'd come out in these real short shorts with a shit-eating, 'I'm on top of the world' grin singing, 'I've got bulletproof legs, I've got bulletproof legs'… and then he'd get always shot in the chest, and die immediately. I've had so many people come up to me and say they loved that. He also did FedEx Pope, which was just him wearing an FedEx box on his head looking like the pope. There was an inventiveness behind them and a silliness for them. Brian McCann and Brian Stack really deserve the credit for bringing so many of those to life. It was something where writers could really roam free and come up with these silly, abstract characters.

"It didn't come from any instruction to be specific. Everyone just got into the spirit. One thing that helped a lot: I practically lived at the show back then. I'd wander the halls with my guitar, making up songs about the writers. We'd act things out, and go off on these long tangents. I would never leave. We would all get on the same page creatively, and I wouldn't have to tell them [what to do]. They knew. Some of the best comedy we ever did was this other bit, Alternative Cable Channels. They were both quick, strange explorations of comedy ideas. It was like this comedy lab."

PIMPBOT 5000
A fifties robot crossed with a pimp from a seventies blaxploitation film.

"We usually delighted in the nonsensical and the silly and the sort of Dali-esque weirdness. So we would have these silly, funny characters on, and one was this robot who was a pimp. We just loved the idea of using a bad, stereotypical fifties robot who would say things like, "I'll cut that bitch," and "I'm going to turn that ho out." He was an immediate success. People loved Pimpbot. And what was funny was that we actually didn't do him for that long. I think Pimpbot was on the show for, I want to say, about fourteen months? We did everything we could possibly think of with Pimpbot. Toward the end, we were just running out of things to do with it, and we realized, 'Okay, we're done with Pimpbot,' and moved on. Easily ten years later, I'd still have frat guys coming up to me on the street, being like, "Where's Pimpbot?" We hadn't done him in ten years!

"I forget who pitched it. We had all these great guys who would come up with these terrific characters, and who created them would get lost in the shuffle. I've learned over time that the worst question you can ask a room full of comedy writers is "Who thought of that?" Everybody remembers it differently. And sometimes one person does the first part, and someone else does the second part. Someone gets it near the basket, and someone else slam dunks it, or tips it in."

CLUTCH CARGO
Famous folks would appear to "visit" the show via satellite, but it was really just a still image of the celeb blended with the moving lips of a writer who's backstage pretending to be that person.

"The summer we were putting the show together, Robert [Smigel] and I were both obsessed with [the original] Clutch Cargo, which was this terrible cartoon from our childhood where they just animated mouths on drawings. It was the cheapest cartoon, and all of us were fascinated with how terrible it was, even as kids. So we all knew that we wanted to try this. We were doing it in test shows, and it worked in test shows. It worked almost right away. We didn’t do Clutch Cargo the first night, but we did it the second night. We did a Clutch Cargo with Michael Jackson back when he was funny, and President Clinton shortly after that. It was kind the perfect way to represent President Clinton. I think to this day, there was never a better impression of him because it actually was Clinton’s face, and then it was this cartoonish exaggeration of his voice. Clinton never said 'Yee-haa!'  but everybody felt that inside he was saying 'Yee-haa!' It was really representing his id. And the Clutch Cargo segments would always come together at the last minute. We'd be backstage yelling at each other as the audience came in. It was all skin of your teeth, just finishing stuff in the nick of time.

"Our show was coming after all the irony and detachment of the Letterman era, which he had done so brilliantly and which he used to kind of invent that format. I remember us talking a lot, for thousands of hours, about how this show would be sillier than that, and almost a little abstract. Really, the show almost had a Second City Television feel to it — like, part Pee Wee's Playhouse, part SCTV, part Warner Bros. cartoon. We made our own world.  And I always wanted the show to be funny even if the sound didn't work."

CARL "OLDY" OLSON
A character actor with the appearance of a 100-year-old who ended being used in numerous sketches.

"We did a pre-taped piece where we got an incredibly old bunch of baseball players and had them play kids. It was like little kids playing really old men. It was sort of narrated like it was on ESPN or something. We showed the piece, and people really liked it. And there was this one actor who was really fantastic, and his name was William Preston. He was the oldest-looking man any of us had ever seen — he looked a thousand years old even though he wasn't that old. And after that bit, we just started using him a lot. In that childish way we liked to do, we called him 'Oldy Olson.' We started giving him more and more lines, and it really got to be where every time he was on, he'd be getting these cheers from 20-year-old fans, sort of this cult following. He could go off on long Shakespearean soliloquies, but then he would start coughing. And he had this, like, tubercular cough that just blew your mind. All of the really great things tend to be an accident, and this happened very organically. One of the last pieces he did was a running-of-the-bulls bit, and I think he fell ill shortly after that, and he was gone. A few of us went to his memorial service, and I actually got up and spoke. He was a good friend to the show."

LAST NIGHT ON CONAN O'BRIEN
A pre-taped parody of those brief "previously on" recaps that appear at the start of a TV drama.

"This was one of those pieces that very much came from my sensibility. I was so obsessed with seventies shows, and the idea was 'Let's recap what happened on the last episode [of Late Night], but it's absolute madness and has nothing to do with a late-night talk show.' It was basically an homage to that era of shows. We would create this complete false reality that our show was kind of like Dynasty or Dallas. It was a lot of me on a yacht with slicked-back hair, and Andy firing machine guns. Or me killing someone. Or me making out with a woman in a bikini and her slapping me, and me then laughing maniacally.

"It was just crazy the amount of work and money that we used to put into these things. I mean, it was 30 seconds or a minute we'd air at the top of the show, and we would have shot at fifteen locations. It was absolutely unbelievable by today’s standards that you would do all those locations. I remember spending a whole weekend in the Brooklyn Navy Yard shooting these things. And then we'd cut them up into these montages with music, and I think it all added up to about probably two minutes and 30 seconds of comedy. That was the period at the very beginning of the show where you don’t know how long you’re going to last, so you’re putting everything you can out there. I used to say that I fed my bone marrow into the first couple of years of that show. Because you’ve been waiting your entire life to get your comedy out there, and then you have this window to do so, and you’re just going to go 130 percent till they drag you off the air. That was one of those pieces."

TIME-TRAVEL WEEK
A February 1996 stunt in which the show would "travel" to a different period of time each night.

"I remember exactly what happened. It was back in the day when sweeps were a big deal. And I remember [then-NBC boss] Warren Littlefield calling, and I think he wanted us to do a  bunch of shows where we pretended we had gone to outer space or something. And I talked about it with him and said, 'I'm okay with us doing a concept, but I don't think it can be the same thing every night, because I think it's going to get old.' So we had this idea that we would just travel through time, and every night would be a different era.

"One of the eras we did was ancient Greece, and we did this pre-tape where we built an actual Trojan horse. We were going to put it in front of David Letterman's studio, and we'd then invade the Late Show. Like in Troy, his people would be suckered into pulling it inside, and then we'd attack. We shot this beautiful pre-tape where we're pushing this Trojan horse over to Letterman's studio. And the whole joke was, as we're crossing Seventh Avenue, a truck hits it and completely destroys it. Also, for the whole show, I'm wearing a toga, and Andy's wearing a toga.  And our first guest was Martin Scorsese. I felt like such an asshole: I'm wearing a toga, I've got a laurel wreath around my head, and I'm interviewing Martin Scorsese. What was great is, he was completely in the spirit of it. He really liked the way we shot the destruction of the Trojan horse. To me, my favorite thing in comedy is incongruity. And he was totally buying into the madness of it all.

"The week happened during this long period of time when we couldn't travel the show. It took us a long time to be accepted at NBC, and while [The Tonight Show] could travel, we couldn't. In retrospect, I actually think that was good. Because when we finally did travel, there was this mania, there was this kind of pent-up energy. People had never seen us before. So audiences just watching on TV could see this big theater filled with screaming people who knew the comedy. I have this real Catholic sense of having to earn it. And we had to earn the right to travel."

PAULY THE NBC PEACOCK
A Peacock puppet who only had great things to say about NBC.

"You have to remember that NBC was in the midst of that crazy run of Must-See TV. There was always good news about NBC, if you can imagine such a time. And sometimes, it seemed like there was this arrogance about how well the network was doing, and how everything they touched turned to gold. They were so dominant. So we had this cartoon Peacock we made into a puppet, with a cardboard jaw. And it would sit on my arm. Anytime I tried to question anything about NBC's lineup that didn't make sense to me, or wasn't doing as well, the parrot would just start screaming at me and changing the subject. NBC would be telling you Suddenly Susan is a hit, so I could question that with Pauly and he'd start squawking at me. He was just this incredibly devoted mouthpiece for the network. In that sort of Carl Reiner-y way, I could be gently skeptical. It felt like you were in the belly of the beast, and you're kicking up trouble.

"I'm sure the network didn't love Pauly the NBC Peacock, but nobody called me up and said we couldn't do it. The times I heard from them was if we made fun of an NBC show, and it got back to the star of the show and they called the network. If they were a big gun, we could get some flack. I think once, when Kelsey Grammer was going through one of his very public crazy periods during Frasier's early years, we did some jokes about it in the monologue, and he wasn't happy. I remember hearing from the network and they said, "You've got to apologize to Kelsey Grammer." And I called him up and we talked about it. We've since gotten along great. They also called me up once when [CBS chief] Les Moonves used one of my anti-NBC bits in his upfronts. He was showing clips of me making fun of NBC. I heard I killed."

ABE VIGODA
The star of Barney Miller and Fish would pop up in numerous bits.

"I maintain to this day that some of the greatest interviews you’ll ever have in late-night television are with the second or even the third guest. And we had Abe Vigoda on as a guest because I loved television of the seventies. And there was this rumor that he was dead. So we had Abe Vigoda on, and he came out said, 'I'm here to say one thing: I'm not dead.' Everybody always assumed that he was dead, because he always looked old. He looked old in The Godfather — when he was 45, he looked old. And you could see right away that the audience loved him. So we said, 'Hey, wait a minute. He’s fantastic, everyone knows who he is, he’s got that iconic face, and he’s great at deadpan.' So we started using him for everything. At the last Late Night show, we shot something where I have to finally release him back into the wild. He couldn't come with us to L.A. He's in a cage, and I let him go, and I'm crying like a baby: 'Run! Run! Just go, go!' And he’s sort of hobbling over the hill in Central Park, and I'm just bawling like a baby. He's still roaming the wild. He’s still out there."

THE REVEREND OTIS K. DRIBBLES
See Conan's description below.

"I hated the Reverend Otis K. Dribbles. It was a guy dressed as a minister, wearing a dog mask, bouncing a basketball badly with both hands, while 'Sweet Georgia Brown' played. I kept saying, 'I hate it, I fucking hate it.' And the writers kept bringing it back in rehearsal, and intentionally kept trying to get me to put it on the air. To this day, some of the writers who are still with me from that era will try to get that on the air. But it was awful. There's good random, and there's bad random. There's good silly and there's bad silly, and you've gotta know the difference. It's like being a sommelier — you know when a wine is ready. And if there's nothing else I can claim after twenty years, it's that I'm the sommelier of weirdness. When it's weird for weird's sake, and arbitrary, I spit it out. But there's a kind of arbitrary silly that's kind of beautiful and sublime. And that's the sort of stuff I'm looking for."