Conan O’Brien just might be the greatest late-night host that television has ever seen, and there are decades’ worth of iconic moments to prove it. Between his classic Late Night show, his notoriously brief stint on The Tonight Show, and his TBS show, Conan forged an impressive career in late-night TV.
From his zany antics with Jordan Schlansky to his hostile confrontations with Stacy Richter, Conan’s late-night career was jam-packed with hilarious moments. These are the funniest bits and segments from Conan’s time as a late-night host.
Conan Hangs Out With His Interns
Conan’s interns prove to be a hilarious foil for his wacky antics as they go along with his over-the-top bits, like pretending to meet them at a party and freaking out about sugar packet organization. This segment builds to a great punchline when Conan realizes his assistant Sona uses his interns to get her lunch by claiming it’s Conan’s lunch order.
Conan’s First TBS Monologue
“Welcome to my second annual first show.” Conan’s first monologue on his TBS show was a masterclass in self-deprecating comedy. He addresses his short-lived stint as the host of The Tonight Show in the opening moments of the monologue. He welcomes the audience to his new show, Conan, and tells them he called it that so he would be “harder to replace.”
The Slipnutz Open For Slipknot
The Slipnutz are three men in sweaters who slip on nuts and often get mistakenly booked for gigs in place of heavy metal band Slipknot. It’s a really silly gag, and it was paid off beautifully when the Slipnutz opened for Slipknot. The crowd of Slipknot fans had no idea what they were watching, and they weren’t happy.
Conan Becomes A UPS Deliveryman
In the old Late Night days, it was always fun to watch Conan try his hand at a job for which he was woefully unqualified. When he spent a day working as a UPS driver, he ended up dropping packages, carrying packages between his legs, and swimming in a customer’s pool. Just seeing Conan parading around in those brown shorts was enough to make this segment a classic.
Conan Forces Jordan Schlansky To Clean His Filthy Office
Perhaps the greatest comic foil for Conan was his associate producer, Jordan Schlansky. Jordan is the polar opposite of Conan: he takes himself really seriously, he never intentionally says anything funny, and he’s a stickler for preparing his body in various ways. Conan and Jordan’s dynamic was at its best when Conan was chastising Jordan.
A prime example of that is when Conan discovered that Jordan’s office was dirty and cluttered. He ambushed Jordan on his way into work and forced him to clean it. This segment was a classic before Jordan even came in the room, as Conan ransacked his office and mocked everything he found in there — including two identical Star Wars action figures.
Conan Rents A Family In Japan
It was always a delight to see Conan go to other countries and dabble in their customs. When he went to Japan, he found an agency that rents fake families out to lonely men, and hired a wife, a daughter, and a father-in-law. Seeing Conan force these actors to laugh at his jokes, and seeing what they’re really saying to each other in the subtitles, is comedy gold.
Conan Goes Apartment Hunting With Andy Blitz
Conan highlighted the absurdity of the New York City real estate market when he took one of his writers, Andy Blitz, on the hunt for an affordable apartment. Blitz is a great deadpan foil for Conan, and it’s endlessly entertaining to watch this unlikely comedy duo test out shower cubicles, meet their potential neighbors, and make ridiculous demands of their real estate agent.
Conan’s Last Tonight Show Monologue
The whole Tonight Show debacle was the most painful period in Conan’s late-night career. Conan was essentially a pawn in NBC’s contract negotiations with Jay Leno, and ended up with the shortest hosting stint in Tonight Show history. In his final monologue, Conan thanked NBC, thanked his fans, implored them not to get cynical, and went out with his head held high.
Andy’s Little Sister
One of the best recurring characters on the Late Night show was Andy’s little sister Stacy, played by Amy Poehler. Stacy had a massive crush on Conan, and whenever she showed up, she’d fawn over him, he’d let her down gently, and she’d launch into a furious tirade of homicidal rage, written beautifully by Brian Stack.
Conan Helps His Assistant Buy A New Car
When Sona asks for Conan’s help finding a new car, he has a ton of fun trashing her current car, chastising fraudulent sellers online, and buying her the cheapest, dirtiest second-hand car he can find. Sona quickly emerged as the perfect sidekick for Conan — she’s a good laugher, an outrageous personality, and she refuses to indulge in his bits — and this segment epitomized their dynamic.
