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We've been in the Cone Zone for 20 years, folks!

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.

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."

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."

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."

What are some of your favorite Late Night segments, ONTD? Old Time Baseball and Finland are hands down my faves.

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