As Conan O'Brien signs off from late-night TV, EW celebrates the sketches and appearances that kept on giving over the years.
Conan O'Brien
| Credit: Paul Drinkwater/NBCU Photo Bank; Todd Williamson/Getty Images; TBS

Late-night TV is about to get less zany, less brainy, less... tall? However you quantify it, the after-hours talk show landscape won't be the same without Conan O'Brien. On Thursday night, the revered and longest tenured late-night host in America is wrapping up a storied 28-year run in late-night, most recently an 11-year tenure on Conan. Here, we salute the essential recurring bits, gags, guests, and laughs that O'Brien lorded over whilst at Late Night With Conan O'Brien (NBC, 1993–2009) and Conan (TBS, 2010–present) — and yes, there's even a key moment from his seven-month stint as host of NBC's The Tonight Show.

In the Year 2000
Late Night With Conan O'Brien (1993)

Sure, no one can predict the future, but no one had more fun trying than Conan. His prognostications were as creative as they were crazed. In a 1993 bit that the show hilariously continued to trot out past the year 2000, the lights would dim, La Bamba would bust out his best falsetto, and Conan and either Andy Richter or a celebrity guest would hold flashlights to their faces and trade outlandish predictive punchlines such as, "Militant atheists take over the United States and order the closings of all churches, synagogues, and T.G.I. Fridays," and "The number '3' will be outlawed, thereby making all omelets either too large or too small." —Dan Snierson

Actual Items
Late Night With Conan O'Brien (1993)

A direct shot at Headlines, in which The Tonight Show host Jay Leno would hold up real-life wacky newspaper clippings. Conan and Andy hard-sold the notion that what you were about to see was entirely real —  "you can't make this stuff up!" — when it was in fact just the opposite. Behold such Actual Items from local newspapers as the carbon monoxide detector that has a "snooze button," or the toilet paper that is so absorbent, "you can kiss large chunks of your ass goodbye." —DS

Staring Contest
Late Night With Conan O'Brien (1994)

Conan and his longtime sidekick Andy Richter usually saw eye-to-eye, but the experience was particularly painful for Andy during these brutal showdowns. While blinking was allowed, breaking concentration wasn't… and that's where the turkey dispensing toothpaste from its nostrils comes in. Never one to play fair, Conan triumphed in almost every staring contest by enlisting an eclectic cast of characters to perform some outrageous acts right next to his desk — which was, of course, smack dab in Andy's eye-line. The distractions ranged from the goofy (person dancing in a panda suit) to the weird (a Nazi soldier whose raised arm doubles as a lever for a water pump) to the downright disturbing (see: the aforementioned toothpaste turkey). The bit ran for years, and if you blinked, you probably missed the only time Andy was allowed to win: May 26, 2000, his final show.  —Kristen Baldwin

Desk Drive
Late Night With Conan O'Brien (1994)

No one or nothing was safe when Conan took his desk out for a spin. Armed with nothing but a green-screen and a steering wheel, the host and Andy — and later, random members of the audience — attempted to take viewers on a leisurely road trip around New York City (or L.A., or Washington D.C., or the Antarctic, or outer space…). The trips often took a wrong turn, resulting in everything from a confrontation with a mob of angry mall Santas to a hair-raising run-in with some power lines. Even though the bit ran for years, NBC never did give Conan a desk ramp for those painfully bumpy steps. —KB

Pimpbot 5000
Late Night With Conan O'Brien (1996)

Introduced in a "New Fall Characters" sketch, this flashy silver hustler — who "combines the sensibilities of a 1950s robot with the dynamic flair of a 1970s street pimp" — probably wouldn't get the greenlight from NBC standards and practices today. (Same can be said for the bit's spiritual sequel, Conan's Pimp on a Treadmill.) Pimpin' ain't easy for humans, but Mr. 5000 had no trouble turning it out — and up. Did Conan ever pay back the money he (allegedly) owed to this metallic menace? Only Pimpbot's switchblade knows for sure. —KB

The Masturbating Bear
Late Night With Conan O'Brien (1997)

When some NBC affiliates in the '90s complained that Late Night was too dirty, Conan listened thoughtfully and responded — by introducing an undergarment-clad bear (well, a writer in a bear costume) who would invariably get ridiculously randy with himself. In each appearance, the Masturbating Bear would start a task, only to soon drop everything and go to town on his crotch, often while his handlers attempted to stop him with cattle prods. "The thing that's funny to me is that he's wearing a diaper and he's also not crudely masturbating — he's batting at his genitalia frantically, which makes it acceptable to [network] standards," O'Brien once told EW. Added late NBC exec Rick Ludwin: "I remember saying, 'Can't we call that character 'The Bear That Likes to Pleasure Himself'?'" Whatever you call the Masturbating Bear, the pleasure was, um, all ours. —DS

Triumph the Insult Comic Dog
Late Night With Conan O'Brien (1997)

Former Late Night head writer and frequent contributor Robert Smigel puppeteered the saucy, old-school, Eastern European-accented canine. Triumph roasted any and all people (and animals) he encounters, whilst brandishing a cigar (that often falls out of his mouth) and a ridiculously versatile catchphrase (add "… for me to poop on" to any sentence). While he famously scored/excoriated at the Westminister Dog Show, Triumph's finest moment was the skewering of Star Wars nerds at the 2002 premiere of Attack of the Clones: [Pointing to the chest of a man dressed as Darth Vader]: "Which of these buttons calls your parents to pick you up?" As O'Brien once summed up to EW: "There's something anarchic about it. You see a dog puppet with a cigar tormenting people holding lightsabers and dressed as Darth Vader and you think: How did we come to this?" —DS

Clive Clemmons' Inappropriate Response Channel
Late Night With Conan O'Brien (1998)

"Ted Bundy was framed" is a weird thing to say at any time, but it's especially bizarre coming from a grandma whose cute grandson just complimented her homemade cookies. Exchanges like these were common on the Inappropriate Response Channel, one of the many niche cable networks that Conan checked out during his Satellite TV segments. (Please, let us never speak of the Max Weinberg porn channel, Max on Max.) Here, legendary (and fictional) British heavy metal guitarist Clive Clemons capped every indecorous rejoinder ("Coffee sure is good today." "Thank God for Saddam Hussein!") with a sick guitar riff and rock-and-roll rallying cry: "In-a-PRO-priate!" —KB

Paul Rudd and the never-ending Mac and Me prank
Late Night With Conan O'Brien (2004)

Warning: You have entered Lucy-pulls-the-football-away-from-Charlie Brown territory. Every time that amiable Hollywood star Paul Rudd had a new film to promote, he'd bring along a clip that he claimed to be from his latest project. (The very first time he did it, in 2004, he insisted that it was a peek at the Friends series finale.) It would always the same absurd clip from 1988 E.T. knockoff flick Mac and Me, in which a boy in a wheelchair rolls out of control down a hill, off a cliff, and plummets into water before a silly-looking alien pops up on the screen with an astonished look. Rudd's prank was as inevitable as Mac and Me is terrible, but it got Conan — and us — every time. —DS

The Walker, Texas Ranger lever
Late Night With Conan O'Brien (2004)

Corporate synergy sounds boring, but it can be a crowdpleaser. When NBC and Universal merged, Conan informed viewers that his shoestring-budgeted show could now show clips of Chuck Norris' CBS law-enforcement drama for free. And so the host pulled a lever that played context-free clips that were campy, confusing, dark, or all three. The most notable clip was one that Conan admitted to being  "afraid" to show — he got up and walked away from his desk after playing it — and, well, let's just say that Haley Joel Osment delivered a line that you definitely were not expecting. —DS

Surviving Jordan Schlansky
Late Night (2001)/ Conan (2008)

Conan's exquisite disdain for his erudite associate producer knows no bounds, though he'd certainly like to bound and gag him. Whether questioning Schlansky's precise role on the show ("various duties"?), busting him for arriving late to work, chastising him for purchasing an espresso machine with company money, or suffering through his pontifications on truffles while the two walked through Florence, Conan was always at his best when thinking the worst of the peculiar, particular, and unflappable Schlansky. —DS

The birth of "Team Coco"
The Tonight Show With Conan O'Brien

Like so many good things in this life, we owe Conan O'Brien's silly nickname to Tom Hanks. On the second episode of The Tonight Show With Conan O'Brien, the host tried out a "Twitter Tracker" segment… which ultimately devolved into an argument between Conan and a growly off-screen announcer who kept calling him Coco. ("Oooh, CoCo Say No CoCo on His Show Show?") Later in the episode, Hanks took a seat on the couch — and led the audience in a rousing chant of "Coco! Coco! Coco!" After just 7 months, Conan's reign as the Tonight Show host was over — but fans rallied around him, declaring "I'm With Coco" through social media. And that's how Coco went from no-no to go-go. — KB

Clueless Gamer
Conan (2012)

"I was bad at that," noted Conan during his attempt to play Middle Earth: Shadow of War with pal Kumail Nanjiani in 2017 — but the statement applies to every single one of the show's aptly-named "Clueless Gamer" segments. Part review, part epic fail video, and all extremely silly, the bit paired Conan with an actual gamer, producer Aaron Bleyaert, who guided the host and celebrity guests through the latest video game releases. When he wasn't getting distracted by random and irrelevant questions — Does Tony Hawk: Pro Skater 5 have in-game snacks? What's the best way to flirt with the strippers in Grand Theft Auto V? — Conan and his guests delivered MST 3K-style commentary about the on-screen action. The riffing was off the charts when Bill Hader joined Conan for a round of God of War in 2018 — and while the gameplay was tragic, the giggling fits were next level.

Sona with the assist
Conan (2013)

Sona Movsesian is Conan's trusty-feisty assistant, his podcast co-host, and an amusing foil who was unafraid to tell her boss that she has enjoyed working for him for the last 10 years, even if there are times when she wants to poison his food and kill him slowly. She traveled with him to Armenia to learn about her heritage, she admirably filled in as a guest when Kumail Nanjiani had to cancel at the last minute, and she and Conan met with the show's HR rep to clear the air — only to fill it with laughter. —DS

Adventures with Ice Cube and Kevin Hart
Conan (2013)

Theirs was a bromance made in buddy-comedy heaven: An OG rapper from South Central, a stand-up comedian with street cred, and a pasty, freckled white guy from suburban Boston. Their relationship first blossomed in 2013, when Ice Cube and his Ride Along costar Kevin Hart joined Conan hired a Lyft for a jaunt around L.A. While they never did find the "good weed spot," Cube and Hart quickly became longtime friends of the TBS show. Nothing showcased the trio's opposites-attract chemistry like their joyride with Conan staffer/student driver Diana Chang. Conan, Cube, and Kevin may not be the most responsible instructors — we're pretty sure throwing pennies out the window and yelling "you're my bitch!" at fellow motorists are not AAA-sanctioned maneuvers — but we'd let them (backseat) drive our car anytime.  —KB

Conan Without Borders
Conan (2015)

Conan brought his show to Ireland way back in 1999, but in more recent years, he truly became an international man of comedy. In a series of compelling globetrotting specials that showcase O'Brien's fleet-footed observational humor (which were branded as "Conan Without Borders" specials, a franchise he will continue on TBS), our host has: tried to raise money in Mexico for the border wall; rented a family in Japan; received punishment from a dominatrix in Germany; visited a Buddhist temple with Steven Yeun in Korea; and delivered a conciliatory speech in Creole to Haitians who were angered over Donald Trump's comments about their country. Indeed, Conan's humor translates across all languages and people. —DS

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