Top 10 Funniest Conan O'Brien Interview Moments

Known for his roles in shows like “The Big Bang Theory,” Simon Helberg is also a skilled impressionist. His work as Robin Williams really excites the “Conan” audience and its host. Not only does Helberg nail the chaotic version of Williams, he’s able to slow everything down for a more subdued impression. The TV star’s accurate portrayal of the “Good Will Hunting” side of the comedian feels just as believable as the crazier one. Altogether, this segment turns into a showcase of the guest’s dynamic ability as a mimic and physical performer. Once he stands up, the actor unleashes a variety of hilarious voices in a whirlwind performance.

Jennifer Garner and Conan O’Brien are having a friendly conversation until the subject of grammar comes up. The actress attempts to correct the host after the latter uses the past tense version of “sneak.” Trying to catch O’Brien in a mistake, Garner calls him out in a moment that draws a strong response from the crowd. A typical show might’ve kept on going without mentioning the incident again. This particular program decides to have a callback later on, with the presenter bringing out a book for reference. He confirms that “snuck” is a word and gets the last laugh in a dramatic finale.

One of the most celebrated talk show guests of all time, Martin Short has created a persona as an insult comic. He channels the likes of Don Rickles in this appearance on the “Conan” show. Rather than stopping him, the host lets Short run wild with jokes about the presenter’s program, career, and more. The comedian goes after Andy Richter before setting his sights on Conan’s looks. It would all seem mean if it wasn’t clearly meant to be a joke. Even the guest’s dog isn’t off limits, making for some funny one-liners and gross-out comedy to finish.

It’s not uncommon for animal experts to bring a little excitement to a talk show. In the case of this “Late Night with Conan O’Brien” segment, Jarod Miller does all that and then some. There’s a capuchin monkey and a snake, but a kangaroo comes by to steal the show. Miller mentions that it’s mating season and struggles to get a firm hold on the marsupial. O’Brien plays up the tension of the moment for big laughs, hiding behind his guest at one point. It all plays out with a chaotic energy that could turn to disaster at any minute. Thankfully for audiences, nobody in the studio gets seriously hurt so everybody can laugh along like it’s no big deal.

No stranger to talk shows, Steve Martin always brings out funny ideas for his interviews that deconstruct comedy itself. This time around he performs a top-ten countdown for Conan O’Brien. Pretending like it’s one of the host’s usual bits, Martin carries on without mentioning that it’s actually a David Letterman premise. O’Brien is unable to stop his guest before he starts the list. The clueless performance from the comedy legend is hilarious as the jokes become meta and even feature a “cameo” from a Paul Shaffer lookalike. As the segment goes along, audiences quickly realize that the comic is dead set on finishing it with complete determination. Martin’s focus ends up being one of the subtle details that build out a classic skit.

For this appearance, the “Saturday Night Live” legend joins Conan O’Brien for a versatile segment. He practically turns his time into a stand-up set with enough jokes to fill a full special. Carvey reminds everyone of his gift for impressions, never missing a beat with a wide variety of celebrity voices. These include funny interpretations of everyone from Sean Connery to Bernie Sanders. The beauty of these routines is that the comedian only uses a few words at a time. Knowing when to step back and let his guest thrive, O’Brien lets the comic perform and provides some hearty laughs in the process.

Among the brightest comedy stars of the 1990s, Chris Farley had a way of lighting up any room. This “Late Night with Conan O’Brien” appearance helps him do that while also capturing the performer at a career high point. He also fondly mentions an impression of Newt Gingrich and reveals his lack of knowledge about real politics. After the conversation steers toward his love life, Farley tries to woo an audience member. His comedic timing makes this awkward moment really memorable, but there’s even more surprises in store. Adam Sandler bursts in like a jealous lover, prompting some amazing reactions from his counterpart. It’s ultimately a quick skit that’s absurd in the best possible way.

If you’re familiar with Bill Burr, you know that he’s always one to voice his opinion. He shows up after Elijah Wood mentions a nightmare about a break-in. Burr helps offer up some advice in a blunt and hilarious way. Starting with some weapon recommendations, the stand-up doesn’t hesitate in recounting his own opinions about home defense. This all leads to some funny observations and anecdotes from his own life as well. By the end of this segment, the comic has everyone laughing with darkly comedic and graphic depictions of home invasions. It all comes out in an effortless way that only this funny man can pull off.

When Norm Macdonald came on a talk show, there was no telling what he would say or do. This made for great television such as this highlight from “Late Night with Conan O’Brien.” The comedian uses every opportunity to butt into the interview with his trademark humor. He even finds time to bash Courtney Thorne-Smith’s career choices. The segment also includes him making fun of her movie with the comedian Carrot Top, with a moment that ranks among Macdonald’s finest one-liners. O’Brien can’t stop the train before it goes off the tracks and we thank him for it.


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

Tom Hanks Watches Whales
After Noticing a Whale in Conan’s Backdrop, Hanks Gets a Huge Splash of Water

Bob Saget Talks “Full House”
The Actor Revealed That He Liked to Prank Fans of the Sitcom

Matthew Perry’s Hockey Joke
The “Friends” Actor Shares Fun Anecdotes Regarding His Native Canada & Hockey

Will Ferrell Shaves Conan’s Beard
In a Comedic Rage, Ferrell Takes off the Host’s Beard in a Hilarious Segment

Sophie Turner Slaps Conan
The Host Tries Out a Crazy Drinking Game That Includes Slaps

This might be the longest-running prank in talk-show history. At the very least, it’s one of the funniest gags in the history of Conan O’Brien’s television career. Paul Rudd’s guest spots almost always include a moment for him to show off his latest film. Instead of promoting the movie, he plays a clip from the “E.T.” rip-off “Mac and Me.” It’s such a ridiculous scene that it always gets a laugh no matter how many times it plays. Rudd’s dedication to the bit never ceases to impress after all these years, turning a funny premise into a legendary piece of O’Brien’s legacy.

Did we forget one of your favorite Conan moments? Let us know in the comments below.