Today marks the 25th anniversary of the debut of Late Night With Conan O’Brien. NBC rolled the dice on the veteran Simpsons and Saturday Night Live writer, plucking him from relative obscurity to take over for no less a luminary than David Letterman. But after a famously rocky start, the series became a springboard for ’90s alt-comedy talent and turned its endlessly sardonic host into a late-night legend. To commemorate its 14-season, 2,725-episode run, here are a handful of The A.V. Club’s favorite clips, which are just as surprising, subversive, and silly today as they were when they first aired.


1864 Baseball

Conan himself picked the remote segment where he played baseball as it would have been played back in 1864 as his favorite on-air moment in a 2012 interview with Piers Morgan, and it’s hard to disagree. Conan’s remote segments are often the best part of any particular episode—see also his interviews with regular folks on the streets of Mexico City last year—but that particular field trip really played to his strengths, as it allowed him to simultaneously get into goofball character wearing a bushy old-timey mustache and play the self-depreciating straight man in interviews with the historical re-enactors on his team. Unabashed silliness and deep nerdery? Sounds like peak Conan. [Katie Rife]


Actual Items

There was something wonderful about the way Conan was able to subvert late-night conventions, by not just shooting spitballs at Leno’s formulas but creating perversions of them. Case in point: “Actual Items,” which poked fun at Leno’s famous recurring “Headlines” segment. The joke, at least initially, was that Conan’s “pulled from the papers” oddities were completely fabricated, unlike Leno’s. But O’Brien also turned it into its own fucked-up thing entirely, creating marketing copy that pivoted organically into violence, surreality, and sex. This early installment, from March 1997, features a VCR that shoots cream, a suicidal dog, genocidal cashews, a disemboweled Easter Bunny, and a bunch of other boorish and depraved punch lines. By the time they get to a baby advertising a strip club, it’s clear that O’Brien’s repeated claims that “you can’t make this up” aren’t entirely serious, but rather a springboard for his team to exercise its own dark humor. [Clayton Purdom]


Andy’s little sister

Advertisement

Advertisement

Long before her stints on Saturday Night Live or Comedy Central’s Upright Citizens Brigade, Amy Poehler had a recurring role as Andy’s little sister, Stacey. She didn’t make many appearances, but her few times on the show were indelible, Poehler’s girlish crush on Conan (even in the face of her Christian-camp boyfriend Andy Daly) slowly escalating into enraged, shrieking mania. Bound by headgear and an irrepressible need to land the great orange-haired whale of her desire, Stacey was a firebrand of psychotic intensity, lashing out the instant things began to turn against her. It’s over-the-top dark and sweetly innocent at the same time, just like the best of Conan’s segments. [Alex McLevy]


Cactus Chef playing “We Didn’t Start The Fire” on the flute

We can all agree: These clips are all some of the best ever offered by a late-night talk show, and they’re all incisive, intelligent, and thought-provoking, and not at all idiotic or arbitrary. Isn’t that right, Cactus Chef playing “We Didn’t Start The Fire” on the flute? [Erik Adams]


The camera gets stuck on Andy

Andy Richter redefined the role of the talk-show sidekick on Late Night With Conan O’Brien, bringing more than amiability and enthusiasm to the couch. His chemistry with O’Brien remains unrivaled in the genre, but Richter delivered some of the series’ standout moments all on his own. In this 1997 episode, the comedian let viewers in on what he got up to while O’Brien was hobnobbing with the rich and famous—namely, smoking, embroidery, and being shaken down by his bookie. Ever the professional, though, Richter doesn’t let it interrupt Oscar winner Marisa Tomei’s soft-sell pitch for Unhook The Stars. [Danette Chavez]

Advertisement

Advertisement


Driving desk

Despite all the great remote segments the show did over the years, there’s a fundamental rule of a late-night talk show: It takes place in a studio, in front of an audience, and with the possible exception of the hallways of the building, there’s not really anywhere else to go. Unless you’re Conan and Andy and have access to a low-rent green screen, that is. The desk driving segments, where Conan would grab an unattached steering wheel and take his host’s desk on a drive through New York City (or a different city—L.A., Amsterdam, and more all made appearances over the years), were some of the most gloriously inspired stupid-smart segments the show cooked up. Whether it was the early experiments with blending the footage into in-studio tricks or the more absurdist transitions depicted once they started to really expand the boundaries of the bit, it was always an unpredictable thrill to see how Conan would navigate the threadbare line between meta and commitment. Plus, how many segments in late-night history end with host and sidekick getting sprayed by elephant urine from less than a foot away? [Alex McLevy]


The FedEx Pope

Say what you like about Cactus Chef, but at least someone had to go out and find a chef’s hat. FedEx Pope, Late Night’s self-proclaimed “least popular character,” was assembled entirely out of things one could find around the show’s offices: a FedEx box, a white bath robe, and dour-looking series writer Brian McCann. The vast majority of great Late Night characters exist almost solely for the purpose of annoying Conan, but few seemed to get his goat as thoroughly as the Pope’s box-hatted antics, which consisted entirely of coming out on cue, getting yelled at for being terrible, and then slinking away backstage. He was, in other words, the perfect Late Night character, a living symbol of the show’s commitment to putting the dumbest possible shit on television, and then delighting in its ability to somehow get away with it. God bless and keep his cardboard-mitre’d head. [William Hughes]


In The Year 2000

In 1997, when Conan and Andy kicked off “In The Year 2000,” the future seemed far, far away. The five-minute bit, augmented by an eerie falsetto theme song, black robes, and flashlights, featured references to numerous ’90s celebs, so not all of them (“zero-population growth achieved by the use of Michael Jordan cologne”) have aged that well. Still, “In The Year 2000” eventually became one of Conan’s most anticipated segments, predicting Colin Powell as the 43rd Batman and hairbrushes becoming known as the “hair go where I want stick,” made all the funnier by the pair’s deadpan yet bizarre delivery. No wonder the year 2000 didn’t even lead to the end of the bit; neither did Richter’s departure, with celebrity guests eager to fill in. Unsurprisingly, “In The Year 2000” was also the first Late Night sketch to be carried over to Conan’s Tonight Show. [Gwen Ihnat]

Advertisement

Advertisement


Paul Rudd and Mac And Me

1988’s Mac And Me has a 0 percent approval rating on Rotten Tomatoes, so if anyone thinks fondly of the infamous E.T. knockoff, it’s probably thanks to Paul Rudd’s tireless efforts and Conan O’Brien’s abiding attitude. For the last 20 years or so, the actor’s been sneaking a clip from Stewart Raffill’s derivative movie into his appearances on O’Brien’s talk shows, starting with this interview on the set of Late Night. In hindsight, the likelihood that NBC would have given Rudd, who was only a guest star on Friends, a clip of the series finale was incredibly low, but O’Brien took the bait then (and again in 2005, and 2008, and...). Although this is one recurring bit that wasn’t O’Brien’s doing, it’s hard to imagine any other talk-show host going along with it time and time again. And it’s a great reminder that O’Brien prized comedy above feeding the Hollywood promotional machine. [Danette Chavez]


The Slipnutz open for Slipknot

Combining the irrepressible amateurism of a lower-tier Muppet Show act and the “fool me once, shame on you—fool me twice, shame on me” schtick of Nick Wiger’s Halloween-time appearances on Comedy Bang! Bang!, the comedy trio of Jon Glaser, Andy Blitz, and Brian Stack slipped on nuts, clowned around, and slipped on nuts. And as O’Brien liked to say, “That was basically their entire act.” Of course, Late Night kept finding ways to bring back the guys and their brown paper bags of peanuts, sometimes in close proximity to appearances from similarly named heavy metal act Slipknot, which should not be confused for The Slipnutz, who slip on nuts, clown around, and slip on nuts. To compensate for one such “mistake,” Glaser, Blitz, and Stack were dispatched to New Jersey to warm up the crowd at a Slipknot concert, a remote segment that doubles as a backstage mockumentary starring Glaser, Blitz, and Stack as their self-serious Slipnutz alter egos. They were destined for greater heights and earlier time slots (Parks And Recreation, Review, and The Late Show With Stephen Colbert, to name a few), but in my eye, they’ll always have those red sweater vests on, prompting a crowd of new metal fans to act not unlike the rabble in the Muppet Theater cheap seats—if that rabble could raise its middle fingers. (This clip receives bonus points thanks to a background cameo from the Walker, Texas Ranger lever.) [Erik Adams]


The Walker, Texas Ranger lever

In early 2004, some corporate merger gave NBC royalty-free access to every episode of Walker, Texas Ranger ever. The result was absolutely depraved: O’Brien became so mad with power that he installed a lever on his set that, when pulled, brought up a completely decontextualized clip from Chuck Norris’ long-running, strangely moralistic modern Western series. Walker had always been funny, but hadn’t yet been exploited for its memetic potential, providing a rich vein of bad-TV yucks for O’Brien to mine. In this early installment, we have a ludicrously over-the-top action scene (“First off, when a guy’s on fire, do you have to kick him out of the window?”), a shot of Walker icily staring down a computer animation of DNA, and a death scene that defies gravity. But it was O’Brien’s application of the lever—lording it over the viewer, teasing it, treating it as punishment—that made the joke so enduringly enjoyable. Wait till the end—when Conan unexpectedly pulls the lever while introducing a guest—for proof. [Clayton Purdom]