Top 10 Times Conan O'Brien Clapped Back at Guests

One of Conan O’Brien’s best guests, Timothy Olyphant developed a strong rapport with the host during his days on TBS. This particular appearance represented the performer’s more casual side. He received ample criticism from the comedian, being mocked for his tennis-court attire. Olyphant attempted to explain his clothes, to no avail. It was all in good fun though, with everyone playing into the bit. Eventually, O’Brien hilariously lost it again as he pointed out the actor’s exposed toes and prominent bruise. This put down generated some of the biggest laughs of the whole segment as the wardrobe choice continued to be judged.

Famous gonzo journalist the late Hunter S. Thompson stopped by for a wonderfully bizarre segment on “Late Night with Conan O’Brien.” The host and writer teamed up for a trip to a shooting range with a twist. Thompson's quirky antics built up to a loud outburst, prompting O'Brien to jokingly question his own safety. This came as a highlight in-between shots of the duo firing at strange and unexpected objects. O'Brien's quick wit and general demeanor meshed well with his guest's unorthodox methods. While probably not as remembered as other classic skits, it did allow for at least one clever observation from the presenter.

The comedic duo John Mulaney and Nick Kroll stopped by the “Conan” show with apparent style makeovers. They lovingly got on the host’s nerves with pretentious statements and non sequiturs, some of which included discussing their future plans in the business. O’Brien sarcastically egged them on until one of Kroll’s statements enticed him to call them out. It was, of course, all a bit played for laughs in a brilliant satire of shallow celebrity culture. That didn’t prevent the presenter from taking his comedic revenge on his two guests, though. Considering the segment was all about poking fun at this kind of behavior, it was only a matter of time before the actors got some pushback.

Bill Burr made many memorable stops on the “Conan” program to deliver his trademark rants. This segment featured some controversial thoughts about women that raised more than a few eyebrows. Once O’Brien started to hit back, Burr realized that everyone was actually misunderstanding him. The host and his sidekick Andy Richter both thought that their guest had said something entirely different. All of this culminated with O’Brien throwing out a hilarious aside about the confusion. Everything came together in a true roller coaster of a talk show appearance, playing perfectly into the group dynamics on display.

In one of the more chaotic moments from "Late Night with Conan O'Brien," the late Norm Macdonald chimed in with thoughts on Courtney Thorne-Smith's career. When she mentioned working with Carrot Top, Macdonald was ready with some jokes. All the while, the host called out the comedian for his subversive behavior. This culminated in O'Brien admonishing the guest and unintentionally setting up another memorable line. His funny retort generated applause, but nobody was quite prepared for Macdonald to return fire so quickly. The entire segment still ranks among the more classic moments in the show's history.

Cult filmmaker Abel Ferrara appeared on Conan O’Brien’s “Late Night” program in 1996, and the result lives in infamy. The director didn’t make the interview easy for O’Brien, giving vague answers that didn’t seem to go anywhere. He even got the host to question his own reality at one point. The comedian produced laughs with his eccentric behavior, while fellow guest Denis Leary and sidekick Andy Richter watched in amusement. But at the end of the day, it was O’Brien’s sarcasm throughout that said it all. Later reports detailing Ferrara's attempts to escape the studio beforehand made even more sense given the final product.

Combining the intensity of Gordon Ramsay and the hilarity of the late Norm Macdonald, this segment on “Late Night with Conan O’Brien” was a beautiful disaster. The celebrity chef tried to teach everyone to cook fish, but things quickly went off the rails. Ramsay and Macdonald performed some verbal sparring before O’Brien yelled at them. Taking aim at the cooking icon’s swearing and visual gestures, the presenter jokingly mentioned that the whole segment would be thrown out. That didn’t stop either party from sabotaging the program, though! At a certain point, the host grabbed a bottle of wine in defiance of it all!

In the 2000s, famous rap rock group the Beastie Boys gave a rare interview on “Late Night with Conan O’Brien.” O’Brien praised them for their longevity, bringing up other acts like the Rolling Stones that have stayed together even longer. Late group member MCA then offered up an opinion of the Stones and their advanced age. That’s when the host saw – and seized – an opportunity to dish out a delightful comeback. Using incredibly articulate phrasing, he turned the awkward moment into a smart comic observation. Even the Beastie Boys seemed to realize what a great clapback it was, and struggled to hold back their smiles.

Near the end of “Conan”’s run on TBS, O’Brien invited on legendary comedian Dana Carvey. The guest provided tons of laughs with his accurate impressions and even tried out new material, prompting the host to cleverly make fun of him. He specifically took offense with the fact that Carvey was using a piece of paper to guide him through ideas. The whole thing was especially funny considering the fact that – as O’Brien pointed out – this was all happening on one of the show’s final episodes. Through it all, the impressionist, his endless vocal abilities, and his interactions with the host provided some much-needed levity.

We all forget our grammar rules sometimes, and this exchange served as a good reminder to freshen up on the concept of past tenses. Jennifer Garner stopped the interview to say that O’Brien was making up a word. The Harvard graduate was obviously caught off guard, but played off the remark until he could plot his revenge. He later brought out a trusty dictionary to expose and explain Garner’s error. The entire moment proved to be one of the more effective clapbacks for the presenter. He relished in the victory, and lived to fight another day with his Ivy League-credentials.