Conan O'Brien’s guest once took their clothes off on live TV and it got even weirder: "May I try your..."
From Ellen DeGeneres’s controversial questioning of guests to Jimmy Fallon’s lighthearted moment ruffling Donald Trump’s hair, the talk show industry has seen its fair share of jaw-dropping moments. However, none compare to one overly enthusiastic guest on 'Late Night with Conan O'Brien'. Completely fascinated by the studio audience, the overzealous guest barely acknowledged O’Brien’s questions. Adding fuel to the fire, he went as far as removing his clothes on air and even convinced O’Brien to follow suit.
In 2002, Roberto Benigni appeared on 'Late Night with Conan O'Brien' to promote 'Pinocchio' and was visibly ecstatic from the start. However, instead of engaging with O'Brien, he seemed mesmerized by the audience, as per The Things. O'Brien, known for his quick wit, joked about interviewing without looking at each other. As Benigni expressed his love for O'Brien, he asked for a hug, then climbed onto the arm of a chair to embrace and kiss him, which hilariously highlighted their height difference.
As the interview continued, O'Brien struggled to maintain structure, at one point asking, "Is there a quiet side to Roberto Benigni?" to which Benigni said, "This is the quiet Benigni." Eventually, Benigni decided to promote 'Pinocchio' in his signature style. He boldly promised to give away his jacket to anyone who didn’t like the film. To make the moment even more entertaining, he convinced O’Brien to swap jackets with him on the spot, saying, "If you don't like the movie I get.. I give you my jacket," then asking, "May I try your jacket?" Once Benigni and O'Brien swapped jackets, the size difference made the moment hilarious. O'Brien's longer arms made Benigni look swallowed in the oversized jacket, while O'Brien's arms barely fit into Benigni's much smaller one.
After laughing at their mismatched jackets, Benigni jokingly asked O'Brien to swap pants as well, saying, "Now may I try your pants?" "You want my pants?" While O'Brien initially refused, Benigni began taking his off, prompting the host to follow suit. Standing in their underwear for a brief moment, they then put on each other’s pants. The result was pure comedy, as O'Brien’s pants were far too big for Benigni and kept falling, while O'Brien’s exposed ankles made him look equally absurd.
While this exchange was indeed hilarious, during Benigni's appearance on 'Late Night with Conan O'Brien' in 1998, his boundless enthusiasm led to his ousting from the interview. From the start, it was clear this wouldn't be a typical talk show appearance, as instead of greeting O'Brien, Benigni danced in circles with the band before finally making his way to the interview area, as per The Things. Rather than a handshake, Benigni leaped into co-host Andy Richter’s arms, hanging off him momentarily.
When he reached O'Brien, the host embraced the actor’s energy by lifting him into the air. Just as things seemed to settle, Benigni turned his attention to the studio audience, setting the stage for even more unpredictable antics. He blew them a kiss before running over and kissing two audience members. O’Brien, realizing things were escalating, stepped in to retrieve his guest. The only way to get Benigni back on stage was to physically lift and carry him away—while Benigni, ever exuberant, waved to the cheering crowd the entire time.
Once O’Brien got Benigni to the interview area, he attempted to start a conversation, but Benigni had other plans. Instead, he enthusiastically praised 'Late Night with Conan O'Brien' saying, "This is the most lovable show I've ever seen in my life. Very lovable... Everything is talking about love, no? Everything, this table, this couch, you! We're all about love." As Benigni continued to rave about love and admiration, he gestured toward the audience again.
Worried that his guest would make another run for it, O'Brien quickly warned, "No. Stay! I'm afraid you're going to run away again."O’Brien then attempted to discuss 'Life is Beautiful' and the Oscars, sometimes looking to Richter for help in steering the conversation. However, when O’Brien mentioned a poll about how much people adored Benigni, the crowd erupted in cheers—prompting Benigni to jump out of his chair and rush toward the audience once more. This time, O’Brien had no choice but to more forcefully carry Benigni back to the stage, trying to regain control of the chaotic but hilarious interview. In the end, O'Brien concluded the interview as he was not able to keep the conversation on track.