Conan O'Brien and Jessica Biel's wild fight has fans asking the same thing: "How does he..."
In 2024, Jessica Biel and Conan O’Brien engaged in a hilarious flirt fight on his show in what was one of the most entertaining episodes. Biel, who appeared on the show to promote her film ‘Playing for Keeps,’ wasted no time addressing their past flirtations. She exclaimed, “I am a married woman now. You can’t flirt with me like you did last time,” referencing her marriage to Justin Timberlake. O’Brien, never one to let a comedic opportunity slip, took this as his cue to roll out two separate video segments, each offering a wildly different take on their past encounters.
In one, he was seen desperately throwing himself at Biel, while in the other, Biel dramatically leaped across his desk, insisting she must have him. In response, O’Brien quipped, “Thank you for letting me shoot it 35 times. It was the greatest moment of my life.” The flirt fight quickly turned into a nostalgic dive into Biel’s childhood, which as it turns out, was unusual to say the least. She described herself as a tomboy who had a rather dark pastime—decapitating Barbie dolls. She shared, “I ended up mutilating [Barbies]. Pulling their heads off, cutting off all their hair, dying them with markers and sticking them on the Christmas tree lights. And they’d light up like these demonic heads,” as reported by The Hollywood Reporter.
O’Brien, always quick-witted, remarked, “You’re beautiful and I love serial killers.” Biel laughed before adding, “I still have the heads. They still go on every year at home.” One can assume she was joking—fingers crossed. Fans and critics understandably had a lot to say on Reddit. A netizen said, “Forgive me if this has been addressed before, and obviously this excludes anything before his marriage to Liza, but how does he get away with flirting so much on the show? The dominatrix from Conan Without Borders Germany, The Tinder bit with Dave Franco, Flirt Fight??” Another chimed, “I’ve actually discussed this with someone. I think it’s mostly because he’s the butt of the joke. It’s clearly not real flirting and most of the bits are him acting like a nerd around his first woman and everyone laughs at how stupid he is.”
Is it weird that my celebrity crush is 100% absolutely @ConanOBrien ...Is that weird IS IT?? 😬😁😅😅
— Ally Maki (@allymaki) October 8, 2016
In agreement, a person penned, “Conan himself would admit that he wouldn't want this clip to be shown anywhere. I'm certain he's ashamed it was on his show.” Another echoed, “F--k that really got me. I don't know how he keeps getting away with it.” Others added, “It does honestly surprise me sometimes. He's toned it way down in recent times, I started digging into his backlog and going back to his late night interviews and even some of the bits (especially from mid 2000s) and man oh man does he walk the line of appropriateness.”
However, not all of Conan’s flirtatious moments have been received as lighthearted amusement. In an interview with Ally Maki, Conan turned the tables when he put her on blast for an old tweet in which she admitted to having a crush on him. As per The Things, rather than simply accepting the compliment, he playfully roasted her, "Hold it. This is the problem here, all of ‘is that weird,’ do you have to qualify it that much? My question is, why can't someone say, 'I got a crush on Brad Pitt, isn't that crazy???' But you act like your tweet is going to blow up the universe." Maki explained, "It was of me channeling my teenage self, you know, you get a little nervous." Whether he’s the one doing the flirting or the one being flirted with, Conan O’Brien knows how to make his interactions with guests unforgettable.
