The 20 best Conan O'Brien late-night bits

One of the most lasting characters in O'Brien history is Triumph the Insult Comic Dog, a fairly cheap dog puppet voiced by Robert Smigel that talks like Don Rickles. He's gone on to appear on Comedy Central Roasts, and last year, he had a political special on Hulu that was really great...for us to poop on. It's honestly incredible that Smigel has never been beaten up, though Eminem came close. Perhaps the greatest Triumph moment came when he interviewed/insulted "Star Wars" fans in line for the "Attack of the Clones" premiere, including a trivia round where every answer was "Who gives a s---?"

Every time Paul Rudd goes on O'Brien's show, he brings a clip. And every time, it's the same bizarre sequence of a boy in a wheelchair rolling down a hill from "Mac and Me," the poor '80s sci-fi movie funded heavily by McDonald's and Coca-Cola. The first time he did it, he claimed it was a scene from the series finale of "Friends," but he's also described it as a scene from "Ant-Man," "Our Idiot Brother," "Role Models," and literally anything he might be required to promote. Judd Apatow actually attended a taping to make him show a real clip from "Knocked Up." Also, if you watch all of the 14 years of "Mac and Me" appearances in order, it actually looks like Rudd is getting younger. 

We don't need to describe what a disaster it was when O'Brien took over "The Tonight Show" from Jay Leno, only to have Leno unretire and start doing his own show at 10 p.m. The important part is, once it was clear O'Brien was leaving, but his show was still on the air, he began a new segment devoted to spending as much of NBC's money as he could. "These bits aren't so much funny as they are crazy expensive," explained O'Brien, describing bits including buying a Kentucky Derby-winning horse to watch Super Bowl footage in a Snuggie made of mink, and dressing up a Bugatti Veyron as a mouse for no reason, and then playing "Satisfaction" to make the whole thing as costly as possible.

It never came to a head until over a decade later, but it's possible that the tension between Jay Leno and O'Brien started with Actual Items, a parody of Leno's Headlines, where he showed goofy headlines from real newspapers. Actual Items made no pretense, throwing in improbably fake newspaper items, while O'Brien relentlessly insisted that you couldn't make this stuff up — how could you — while obviously making it all up himself.

Perhaps the most controversial character in O'Brien's history, the Masturbating Bear is a diaper-wearing bear who gets nervous when he's asked questions on camera. And, well, then he starts acting out inappropriately. (We can't show him for obvious reasons.) The show has tried to control him with, er, handlers, frozen him in carbonite, like Han Solo, and even temporarily replaced him with "The Self-Pleasuring Panda," but he just keeps masturbating – and winning the show Emmys.

 Note: Though Louis C.K. wrote for the show, he was not the Masturbating Bear.

During the writer's strike in 2008, O'Brien had to host the show, but he didn't want to defy the WGA picketers. So for weeks, the show went on without any scripted segments altogether, where O'Brien had to improvise bits to kill time, like spinning his wedding ring on the desk. This turned in to an intense pursuit, with O'Brien attempting to break his own personal record and eventually consulting with an MIT professor to achieve the most frictionless spin. The show is obviously better with a writing staff, but this proved O'Brien could construct comedy out of the flimsiest premise possible.

O'Brien's first televised trip outside of North America came out of a segment where he insulted every country in the world, in alphabetical order, in a piece called "Conan Hates My Homeland." Finnish viewers began preemptively protesting the segment, leading O'Brien to prematurely insult them, then excessively apologize and denounce "the hated Swede." When viewers pointed out that he looked like Finnish president Tarja Halonen, he devoted an entire show to his journey to Finland. Later, this became a more regular feature, like when he accompanied his assistant Sona on a trip to Armenia and a trip to an Air Force base in Qatar with Michelle Obama.

When NBC acquired Universal, O'Brien claimed that gave the show the right to air clips from "Walker, Texas Ranger," free of charge. This was done using the "Walker, Texas Ranger" Lever, which when pulled, produced a short clip from Chuck Norris' TV classic. All of the clips were presented with zero context, usually involving some wildly violent or cruel act, but they saved the most disturbing Walker clip for years. Get well soon, Haley Joel!

Before she was Leslie Knope, Amy Poehler was Richter's little sister Stacy, a teenager with headgear who had a big crush on O'Brien. She was sweet and cute – that is, until O'Brien rejected her or mentioned a girlfriend. And then she exploded with the rage of a thousand suns, screaming and threatening Richter with horrific violence. It's a shame O'Brien never gave her a shot, because Stacy had true passion.

Slipnutz is one of the delightfully dumbest things O'Brien has done, featuring Jon Glaser, Andy Blitz and Brian Stack as a khaki- and vest-wearing trio who scatter nuts on the stage, sings about slipping on nuts and then slips on nuts. That's all they do. It's, of course, based on the costumed heavy metal band Slipknot, except somehow even dumber. O'Brien brought them over and over, always with an excuse for their previous failures, to do things like plug their Greatest Hits DVD and their tribute album. Eventually they got to open for Slipknot at the Continental Arena. Luckily, they were not murdered.

One of the unsung heroes of O'Brien's show was writer-performer Brian Stack (pictured far left) who played a wide array of characters like the Coked-Up Werewolf, Frankenstein and Artie Kendall, a dead Bing Crosby-esque crooner whose ghost haunts the studio. At first, O'Brien enjoys the songs, which turn out to be misogynist, pro-child labor, Hitler-sympathizing and, once O'Brien gets mad and shows his "hot Irish temper," vehemently anti-Irish. And still ends all his songs with a delightful, "ba, ba, ba, boo" or even "Hitlery-hoo."

Preparation H Raymond is a man with comically large ears, who walks through the audience singing and passing out Preparation H. He sometimes talks about current events, sort of, but the meat of the sketch is the song, all about how "Raymond's here to help," and of course, hemorrhoids. Why does he sing? Because the O'Brien's writers realized union rules meant they got paid extra anytime they sang a song in a sketch. And, of course, the greatest comedy comes from poverty and avarice.

When O'Brien visits a baseball league in Long Island that plays by 1864 rules, it starts with him making fun of all the nerdy baseball re-enactors, especially when he finds a granola bar in one of their pockets. But partway through the segment, he dons a uniform and gets into the game himself, and it becomes truly delightful. The segment is jam-packed with wonderful moments, but the most beautiful part is his flirtation with a female fan who is incredibly committed to the historical role-playing. When he aggressively asks if her (fake) father is a farmer, and she says that "he's passed," we're pretty sure he falls in love.

O'Brien has little interest in video games and an even lower level of skill, so Clueless Gamer puts him in his wheelhouse: failing at an activity while making fun of others. It became a popular segment, yielding a web spinoff, but the best segment was a Super Bowl special featuring Marshawn Lynch and Rob Gronkowski playing "Mortal Kombat." Gronk is as Gronky as ever, but Lynch charms O'Brien and also makes some disgusting things happen with his finishing moves. Everyone involved in this segment deserves Skittles.

A great vehicle for brief, high-concept premises, O'Brien loved to fire up the satellite and check out what bizarre channels were available to him. One of the highlights was the Max on Max channel, featuring bandleader Max Weinberg making out with...bandleader Max Weinberg. There's also the Toddlers With Too Much Responsibility channel, the Sexual Harassing Skeleton Network and, the greatest/weirdest of all, Clive Clemons’ Inappropriate Response Channel. Inappropriate!

One of the show's first classic bits was the Staring Contest, where O'Brien and Richter would silently lock eyes for minutes. O'Brien just had to keep looking, while Richter had to deal with a series of weird and disturbing things in his field of vision: the Hatfields and McCoys looking at pornography, a child removing a wig and a lot of appearances from Spock and Abraham Lincoln. Only on Richter's final "Late Night" episode did they reverse things and subject O'Brien to the horror and distractions, and Richter finally got a win.

In The Year 2000 fit in to the classic O'Brien paradigm of a high concept paired with a low budget. Richter and O'Brien donned black robes and illuminated their faces with handheld flashlights, like they were telling ghost stories, and looked ahead to the horrifying future of the year 2000. Of course, they started the bit in 1997 and only updated it to the year 3000 in 2009. The star was trombone player Richie "LaBamba" Rosenberg and his falsetto In the year 2000s, which laid the groundwork for LaBamba to take over as the target of O'Brien's jokes about deviancy when Max Weinberg left, and eventually, he was a plexiglass-encased icon during the later I'm With Coco rallies.

Another unnecessary-singing Brian McCann character, Mick Ferguson has gotten bulletproof legs, although they "cost him a fortune." Unfortunately, he gets shot in the chest in every appearance, despite the show's supposedly thorough security measures. 

James Corden has Carpool Karaoke. Jerry Seinfeld has "Comedians in Cars Getting Coffee." So when Tom Cruise came on the show to promote "American Made," O'Brien set up a car with cameras to film them...driving. That's it. Just driving around London. It's a wonderfully uncomfortable trip, as Cruise tries to salvage the interview while O'Brien seems mainly concerned with roundabouts and pedestrians. O'Brien's Lyft rides with Kevin Hart are also great, but they don't have quite the delightful squirminess of cruising with Cruise.

When O'Brien moved his show to California, he needed a new repertory of sketch performers. Two of the best new ones on the TBS show were Jon Dore and Rory Scovel, who first appeared in a sketch together after they'd both been accidentally booked for the show, so they'd perform their stand-up sets simultaneously. But the high mark was when a seemingly normal stand-up set with Dore was interrupted by Scovel playing a distracting usher, culminating in everyone switching jobs, Dore ending up the host and a hapless O'Brien working as the usher.

While these aren't planned bits, any time that Norm MacDonald goes on O'Brien's show, things can easily go off the rails. Especially back in 1997, when Courtney Thorne-Smith came on to promote her upcoming movie with Carrot Top. The producers couldn't have been happy with MacDonald interrupting her interview to suggest a Carrot Top film would be called "Nine-and-a-Half Seconds" but then he strikes gold when he suggests any movie starring Carrot Top should be called "Box Office Poison."