Top 10 Conan O’Brien Moments

Our ten favorite Conan clips from over the years.

Johnny Firecloudby Johnny Firecloud

Top 10 Conan O'Brien Moments

"Late Night" host Conan O’Brien is about head West to replace Jay Leno as host of NBC’s "Tonight Show" in June, and he’s making the most of his final week at the studios in New York, running through montage after montage of best-of clips from the show. To celebrate 16 years of late-night laughs, we’ve compiled our own Best Of Conan collection for your gut-busting enjoyment!

10. Conan O’Brien Hates My Homeland

"Late Night" received many angry letters from viewers in Ukraine after a bit aired mocking that nation. In New Euros, the joke was an image on a Ukrainian Euro Coin depicting a man in Eastern European dress with four arms, waving, with the caption on the coin saying "Over 17 years since the Chernobyl Accident". O’Brien had no previous idea that his show even aired in the Ukraine, and as a result set out on a mission to dole out rapid-fire insults of every country on Earth in alphabetical order, to determine where else the show is being aired without his knowledge. Announcer Joel Godard then proceeded to tell insulted viewers around the world a real address to send their angry letters.


It’s worth noting that an announcer on Finnish entertainment channel SubTV asked people to defend Finland before Conan got around to insulting it, and mail from Finland began pouring in before the bit had even gotten to the letter F. Conan responded by assuming the Finnish "just couldn’t wait" to be insulted and skipped ahead in the segment to attack Finland. After a spectacle involving a formal apology and transferring his fake hatred over to Sweden, Conan realized that he bears a resemblance to two-term president Tarja Halonen, which eventually led to a short visit to the country in mid-February 2006.

The sketch continued, but on August 9, 2007, Zimbabwe was the last country to be featured, ending the bit after three years.

9. Will Ferrell Gives Conan A Birthday Leprechaun Dance

Conan always tends to bring out the more colorful character in his guests, but when the guest starts out as a colorful character, where do you go from there? Into the absurd, of course. This litle birthday dance was just as memorable as it was nauseating, if only for the fact that Conan and Ferrell work so well together.

8. Conan Interviews Hunter Thompson

I don’t know how the hell this managed to stay beneath my radar for all these years, but it’s an utterly classic moment in television. Conan interviewing Hunter Thompson is one thing; Conan and Hunter pounding whiskey at Owl Farm and shooting fully automatic assault rifles is another beast altogether. Pay attention around the 2:50 mark, when shit gets truly weird. And notice how Conan doesn’t get a single question in the entire “interview.”

“One of the strangest guests I’ve probably had on the show was the legendary author and creator of gonzo journalism, Hunter S. Thompson,” O’Brien said as an introduction to a re-airing of the now-legendary interview. “Hunter Thompson cultivated a reputation not only for his erratic behavior but for producing some of the best writing of the last century, including Fear and Loathing in Las Vegas.” Noting that the good doctor refused to come to the studio for an interview, O’Brien explained the author agreed to shoot a remote segment “and I met him on a farm in upstate New York to shoot guns and drink hard liquor.” Adding, “He probably expected me to say that’s not going to happen … we brought a camera crew, and here’s what happened.”


7. Celebrity Secrets

This popular bit features celebrities in a jail cell, smoking a cigarette and pounding hard liquor, spilling some ridiculously false "secret" that was previously unknown about them. One featured Gwyneth Paltrow admitting that anytime before she starts a new film she kills a hobo with a hammer, as well as a love for porn. The very best one features Snoop Dogg, and we couldn’t find the clip (let us know if you do), but it went something like this:

"Before I was called ‘Snoop Dogg’ I was called ‘Snoop Doggy Dogg.’ Before that I was called ‘Snoop Diggity Doggity Dogg.’ Before that, I was just called, ‘The Phantom.’"

"Last Christmas I put on a Santa Claus mask, and I said to three of my ladies, ‘ho, ho, ho.’ They didn’t think it was funny."

"It’s true, Dr. Dre is not a real doctor. I just wish he had told me that before I let him remove my pancreas."

"When I go to restaurants, the waiters always ask me if I want a doggy bag. I’m tired of that. All you waiters, stop asking me if I want a motherf***n’ doggy bag."

6. Fake Celebrity Interviews

Bill Clinton was enormously popular in this skit, which was based on the old "Clutch Cargo" cartoon technique of using real human lips on fake cartoon heads. The bit relies heavily on the low-budget filming method Syncro-Vox, with a lowered TV screen in place of where the guest would actually sit. A still image of a celebrity is featured on-screen, with a live video feed of the mouth of the backstage impersonator (usually  either Robert Smigel or Brian Stack). The impersonations range from George W. Bush to Barbara Bush (who’s appropriately given a gruff, manly voice), Bill Clinton, Hillary Clinton and Martha Stewart, Arnold Schwarzenegger, Michael Jackson, Sammy Sosa, Barry Bonds and so on.

Here’s a recent clip featuring A-Rod:


5. Conan Works For UPS

Big Red suits up in the standard brown uniform and goes through a hilarious crash-course in training that includes a Patton-like speech to his co-workers, a disastrous driving instruction and an invasive home delivery.

4. In the Year 2000

This bit is typically performed after a celebrity guest has been introduced and finds O’Brien, band member Richie "LaBamba" Rosenberg and the selected guest wearing black robes, futuristic-looking collars and a lit flashlight held under their face. Between La Bamba’s high falsetto wails of "In the year 2000…", O’Brien and the guest alternate delivering jokes, often based on current events, in the form of humorous predictions of what will happen in the year 2000. The sketch was obviously invented prior to the actual year 2000, but has carried on almost a decade later. The second-to-last prediction commonly involves Conan mocking his guest, while the last prediction involves the guest mocing Conan in return.
Here’s a great one with Stephen Colbert:


3. Conan vs. Stewart vs. Colbert: Who Made Huckabee?

Conan’ recurring mock feud with Comedy Central hosts Stephen Colbert and Jon Stewart over who sparked the short-lived campaign success of presidential candidate Mike Huckabee rapidly became one of the greatest moments of any of the three hosts’ shows. Conan argued that the popularity of Huckabee’s biggest high-profile supporter Chuck Norris was the result of his own Walker, Texas Ranger Lever sketch, therefore "Conan made Huckabee." Colbert, however, claimed that "Colbert made Huckabee" after giving him the "Colbert Bump" on his own show, a measurable stat in the polls. Following a series of cross-show statements, Conan, Colbert and Stewart each presented increasingly ludicrous reasons why he was the cause for Huckabee’s success – while cutting down their rivals in the process. The feud culminated in a final showdown between the three on "Late Night," making for a hilarious battle royal.

2. Triumph the Insult Comic Dog

Wednesday’s episode of "Late Night" reminded me that, despite his low-brow vulgar annoyance, Triumph brings some of the most hilarious insults ever televised when he’s on a roll, such as making fun of  Star Wars maniac fanboys in line for Attack of the Clones:

Triumph’s brutal appearance at Comic Con also deserves an honorable mention, for sure:



1. The Walker Texas Ranger Lever

The summer of the Walker Texas Ranger lever on Conan was a glorious one, inspired by NBC’s purchase of entertainment company Universal in early 2004, thus creating NBC Universal. Conan put two and two together and unleashed the Walker, Texas Ranger Lever, which allowed him to play a video clip from the show any time he wanted, without paying any royalties, just by pulling the yellow-topped red lever. The comedy usually intensified by the choice of clips chosen from the Chuck Norris series; in other words, Conan had a knack for taking things out of context. Here’s a few hilarious examples: