Pius Princewill
Conan O’Brien has experienced plenty of uncomfortable moments during his years on the late-night circuit, but President Donald Trump’s appearance on his show in 1997 might have been the most awkward one of all. “The first time we had Trump on our show, I asked him a question that I’d always wanted to ask someone who proclaimed to be a billionaire: ‘How much money do you have on you right now?'” O’Brien recalled for Rolling Stone. “He sort of said, ‘I don’t know, I maybe have some.'”
O’Brien pressed the businessman to look in his pocket, which he did. “He clearly found something,” the comic remembered. “I saw his face change, and I could see that he didn’t want me to know what it was.” He added, “So I reached over and I was like, ‘Come on, come on.’ I made him pull it out — and it was a condom. He said, ‘Practice safe sex everybody.’ He was in-between marriages at the time.”
Once the show cut to commercial, O’Brien could tell that Trump was “pissed” and “mad.” He added, “I don’t think he said goodbye to me, and he walked over to my producer and said, ‘That’s the last time I’m gonna be on this f***ing show. He humiliated me in front of everybody.'”
Trump “stormed out” on O’Brien, but it wasn’t his last time on the show, as he had “seven more” appearances throughout the years. Go figure.
Written by: Nicki
