Top 10 Most Chaotic & Unhinged Conan O'Brien Moments

“Conan” (2010-21)
Tom Cruise’s talk-show appearances often promise adrenaline-fueled adventures. However, Conan has another idea, and it’s truly groundbreaking. He meets Cruise in London, and they just drive around just like any of us might with a friend, from the small talk to shushing the passenger at a particularly tricky rotary. What makes this bit so iconic is that there’s nothing in it, but Conan’s commitment to the joke makes it that much funnier. Some comedians take their guests for coffee; others have car-wide singalongs, but Conan? Well, he traps A-List celebs in cars and just drives around aimlessly. It’s a long segment, yet it never loses steam, thanks to Conan.

“Conan” (2010-21)
If you ever call your favorite takeout joint and hear Conan O’Brien’s voice on the other end, you’re probably never getting your food—you have been warned. His energy with the kitchen staff is absolutely hysterical, but customer interactions really ramp up the commotion. There’s the woman who rejects her delivery because she seemingly doesn’t recognize him. He finds another taker, who accidentally spills coffee on him as thanks. Then, there’s the kind window woman who distracts him from eating someone else’s order. He also swaps a delivery with Thai food after handing out its original contents to strangers on the street. If you’re hungry for more, there’s also the time he unleashed chaos at a Taco Bell.

“Conan” (2010-21)
Working behind the scenes on “Conan” must have been quite the experience, especially for Jordan Schlansky. As one of the show’s associate producers, Schlansky often found himself in the spotlight of Conan’s playful antics, and we loved to see it. When Schlansky rolls in late for work, Conan does what any good boss would: sit in his office and wait for him. While he waits, he gives the audience a tour of the area. He’d also make Schlanksy clean the place up in another equally hysterical segment. Anyway, the duo’s wildly entertaining dynamic ensures that their shenanigans never fail to leave us in stitches, no matter where they take place.

“Conan” (2010-21)
Conan’s stint with a Civil War reenactment group is comedy gold, as he struggles to part with modern comforts. Still, that doesn’t mean he doesn’t fully throw himself into the occasion. His hilarious attempts to fully embrace the old-timey setting have everyone in stitches, including his fellow reenactors. Watching him get into character as Jedediah Longtree is also pure comedic genius. The guy has clearly been through a lot, and the actual battle hasn’t even begun! Yet, Conan proves he’s just as effective on the battlefield as he is anywhere else. Still, Jedediah has big plans for when this conflict ends, and you know what? We’d be tuning in for sure!

“Conan” (2010-21)
Nothing can put a friendship to the test quite like navigating an escape room. However, Conan isn’t just there with a friend; he’s there with Jordan Schlansky, and well, we already know how their dynamic works when their exit isn’t sealed off. While Conan won’t break any escape records, he’s a champ at giving up and getting sidetracked. Detective work isn’t his strong suit, and he actually does very little to help, but his bumbling adds plenty of laughs. If you ever find yourself stuck in an escape room with Conan, you’ll probably want someone else to help you crack the clues while he cracks you up from the corner.

“Late Night with Conan O'Brien” (1993-2009)
We’ve already seen how Conan fares in old-timey environments. This time, he goes back to 1864 to check out an authentic baseball scene—well, authentic-ish. We learn that farmers are super into the sport, and Conan learns some 1864 baseball lingo. We also meet some of the team’s biggest fans, like this woman who, despite Conan’s best efforts, never breaks character—she even manages to break him! Honestly, her commitment to the role creates the most hilarious back-and-forth. Of course, things reach a new level of unhingedness when Conan fully embraces the times and joins the game. We just hope the real 1864 team had someone like Conan to pump them up before a match.

“Conan” (2010-21)
Some of the funniest and most chaotic moments take place backstage at Conan HQ. Watching him hang out with the interns is a riot! Meanwhile, if we had our annual reviews with him, we’d probably look forward to them! And tell us you wouldn’t get all Conan on your colleagues if you found out they were bogarting free food! Still, perhaps nothing is funnier than his commitment to helping his assistant, Sona, track down her missing mug. While conducting his investigation, he ends up learning a lot about the people who work for him. Eventually, he tracks down the missing item, but there’s an unexpected plot twist. Is Sona grateful for the returned mug?

“Conan” (2010-21)
How many people can say their bosses taught them how to drive? Fewer can probably say they were instructed by Conan, Ice Cube, and Kevin Hart. It’s a recipe for chaos as the latter two bring profanity-fueled road advice that would be better left at the curb. For instance, we don’t imagine many driving lessons include stopping off for, erm, recreational supplies— although, it makes Hart’s chat with the cop that much funnier. By the end, wrapping up at Popeyes seems like the only logical conclusion. This isn’t the only time the trio get in a car together, and honestly, the fact that it didn’t blow up like other famous car segments is a comedic injustice.

“Hot Ones” (2015-)
Apparently, O’Brien was a hot commodity among “Hot Ones” fans, and he was determined to bring the heat. Indeed, the show has seen its fair share of wild reactions, but O’Brien’s take is arguably the Matasanos Hot Sauce of the entire series. At first, he questions if his Irish taste buds can handle it. Yet, he confidently powers through, essentially turning every moment into the Conan show. However, things truly go off the rails when the heat starts to get to him. From then on, everything descends into anarchy. It definitely brings a whole new meaning to masking your pain with humor. It’s a meme-worthy level of unhinged, and we’re very here for it.

Before we unveil our top pick, here are a few honorable mentions.

He’s Not Here to Horse Around, Okay, Maybe Just a Little

If Conan Did Commercials, We’d Probably Be Broke!

We’d Watch It with This Commentary on Every Single Time

He’s a True Master of Chaos

We Don’t Think Gal Gadot Has to Worry About Her Job

“The Tonight Show with Conan O'Brien” (2009-10)
In 2009, Conan succeeded Jay Leno as host of the “Tonight Show.” But in a surprising turn, NBC reinstated Leno the next year. It was a PR nightmare from start to finish. Still, Conan was determined to leave his mark, and it would cost NBC. A lot. With nothing to lose, he decided to go all out and blow the budget. Until this moment, we didn’t even know we needed to see a Bugatti dressed as a mouse with the Rolling Stones blaring in the background. The whole stunt reportedly cost $1.5 million. But can you really put a price on this level of wild entertainment? It’s pure, unadulterated hilarity, and we’re here for every penny spent.