The Best Late Night with Conan O'Brien Sketches

The Funniest Late Night with Conan O’Brien Live Remotes

It’s 2025 and everybody still loves Conan O’Brien. And why shouldn’t they? Not only is he a fantastic comedy writer, a warm interviewer, and willing to fully commit himself to any joke, no matter how silly or stupid, but he also just seems like a nice guy. And this weekend he takes on the impossible task of hosting the Academy Awards, a job that has broken much lesser comedians than Conan.

I’ve never seen anybody say a bad word about Conan as a person, and the fact that he still seems so genuinely humble over 30 years into a career that couldn’t have happened if he wasn’t extremely driven is a testament to how fundamentally decent he is. His recent gonzo appearance on Hot Ones reminded the world how purely committed to comedy he is, and his Max travel show Conan O’Brien Must Go have him back on our TVs after too long of an absence. It’s a perfect time to look back on his excellent body of work, especially the best live segments he did on his first talk show.

His late night career spanned almost 30 years and three shows on two networks, but O’Brien’s comedy legacy rests on the fantastic work he did on Late Night with Conan O’Brien from 1993 to 2009. He preserved the irreverent, anarchic spirit of David Letterman’s time on the show, but with a lighter, goofier, more absurd bent. And as funny as Conan’s interviews could be, and as memorable as the show’s characters are, the best part of Late Night was his remotes. These comedy sketches let Conan get out of the studio and interact with everyday people, usually to hilarious effect. They should be mandatory viewing for anybody who somehow gets the chance to host their own TV show.

For years it was hard to watch these old clips from Late Night. Most of O’Brien’s time on the show came well before YouTube or streaming, and the best fans could do was occasionally find dodgy uploads from old VHS tapes. Fortunately O’Brien’s Team Coco has been uploading these classic sketches to the Conan Classic website and YouTube page over the last several years, letting everybody watch high quality versions of them whenever they’d like. And since it’s been a while since we’ve written about them here at Paste—or about Conan O’Brien and his influence on the talk show and TV comedy—now’s a perfect time to look at five of our favorite Late Night sketches.

Conan Plays Old Timey Baseball

Probably the most beloved Conan sketch of all time turned 16 a couple of weeks ago, which, yeah, makes me feel seriously old. Conan’s visit to the Old Bethpage Village Restoration, where reenactors play baseball like it’s still the 1800s, sums up everything good about Late Night and Conan’s approach to comedy. It’s fixated on a weird, niche activity that most people wouldn’t ever consider, and somehow makes fun of it and the people who do it without ever feeling mean-spirited. It’s also a fantastic outlet for Conan’s more whimsical and absurd side. And with the 2020 Major League Baseball season still delayed, it’s probably the best diamond action you can find right now.

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Conan Goes to Houston to Find Viewers

Not all NBC affiliates were happy with Late Night in its early days. The NBC station in Houston notoriously scheduled the show well after it’s official time slot, dumping it to 2:40 a.m. CT, after reruns of Ricki Lake, Jenny Jones and the nightly news. That kind of disrespect was a running source of hilarity for Conan in those early days, so of course he headed to Houston in search of anybody who might be watching his show in the middle of the night, or even just recognize him. The craziest thing about this is that it was made in 1997, almost four years after he took over Late Night, and well after it had finally found a loving, steady audience.

Conan Records a Song in Memphis

Conan’s first year on Late Night was a disaster. Bad reviews and low ratings seemed to doom it right out of the gate, and with NBC refusing to hand out a long-term renewal (it would only renew the show for 13 weeks at a time until 1995), O’Brien and his staff never felt comfortable in those early days. Conan and his show was a bit of a national punchline in those early days, and that inspired a number of sketches early in the show’s life. This sketch from October 1994 has to be seen in that context; it’s not inherently funny to see a talk show host try to record an original song at Sun Studios, but it’s hilarious when Conan does it because, first off, he’s just a naturally funny person, but also because the song he wants to write and record is about how lonely it is to be a not very successful talk show host. This self-effacement and lack of arrogance became one of Conan’s strongest trademarks, and has persisted even when his career is thriving.

Conan Gets His Own G.I. Joe Doll

In 1999 Hasbro promoted the 35th anniversary of G.I. Joe by conducting a nationwide search for a real hero to base a new figure on. So of course Conan went to Hasbro headquarters in Cincinnati to pitch his case. The sketch runs through the whole process of how a G.I. Joe figure is designed and produced, with Conan providing commentary throughout. At the end he has his own Conan O’Brien-headed Joe prototype, years before Funko Pop turned everybody who’s ever been on TV into their own collectible toy.

Conan Forms the Boy Band Dudez A-Plenti

2000 represented the glory days for crappy prefab boy bands. One of the many pieces of pop culture detritus that tried to float on the boy band wave was ABC’s reality show Making the Band, whose first season tracked the formation of the band O-Town. Late Night parodied the inherent absurdity of that whole scene with this sketch, in which Conan O’Brien becomes the impresario for the brand new boy band Dudez A-Plenti. You don’t have to have first-hand memories of 2000 to enjoy this ridiculousness.

Senior editor Garrett Martin writes about videogames, comedy, travel, theme parks, wrestling, and anything else that gets in his way. He’s on Twitter @grmartin.

The Funniest Late Night with Conan O’Brien Live Remotes