“Nipsey Russell isn’t available? Well, then try Donald Trump. Donald will do it.”
As Conan O’Brien recalled to Rolling Stone in 2019, there was a time in his career where he came to rely on the billionaire who lived just a few blocks away from Rockefeller Center.
In 2004, for example, the newly-minted reality TV host joined O’Brien for a bit entitled, “Trump Secrets!” He’d also fill in as a last-minute guest, like in December 2005, when he discussed The Apprentice and his personal life, including the imminent birth of his son, Barron.
But while he eventually became a regular, Donald Trump’s very first appearance on Late Night with Conan O’Brien was almost his last.
This week on the Late Night Time Machine, we travel back to the of night December 10, 1997, when Conan O’Brien, then just four years into his now-legendary late-night run, asked Trump what seemed like a fairly innocuous question.
“I’m curious about something, because I don’t get to talk to that many very wealthy people,” the host begins. “How much money do you carry on your person? How much money do you have on you right now?”
The audience and Trump laugh. But then it seems as though Trump’s mental gears begin spinning. “Well, do you want me to… uhhhh,” he says. Perhaps Trump wasn’t carrying any cash at the time. As we know by now, Trump’s instinct is always to perform. It is inconceivable that he would decline or offer an excuse. Instead, he pivoted right into a mistake.
“Woah. Oh, if I showed you what I have in my pocket right now…” Trump says with a smirk. O’Brien, the natural, sells the moment. He puts on a confused face and slowly turns towards the audience and then looks into the camera. A pause. Then: “No, no!” he says, as Trump begins to lower his hand.
“Let me see, there is something in the pocket there,” Trump says, instead reaching into the outer pocket of his suit jacket. He pulls out a small object and quickly conceals it in his hand. Trump looks down, perhaps wondering if he is about to make a mistake.
“Do you carry a lot of mon—” O’Brien asks, perhaps trying to save him. But Trump cuts him off, giving a laugh and quickly putting the object back in his pocket. “No, I won’t show you,” Trump says.
O’Brien, as all good hosts would do, insists on seeing the object. “No, no, no! Let me see that,” he yells, reaching across Trump towards his pocket. Trump then holds up the object and declares: “Safe sex everybody!”
The audience cheers as O’Brien asks to hold the object, now obviously revealed to be a condom. The camera cuts to O’Brien as he holds the condom up and places it on his desk. “Is that a great ad?” Trump asks O’Brien, smiling ear to ear.
Trump, sensing what the viewers must be thinking, quickly says, “That was not a prop.” To which O’Brien quickly replies, “Donald, what the hell is happening with you?!” “It’s terrible,” Trump says, laughing. “You should get on some kind of drug,” O’Brien says. “Just calm down a little bit.” Trump was a single man at the time, having separated from his second wife, Marla Maples, earlier that year.
The host then pivoted away from the funny if not a bit awkward moment and all seemed to be well. Two decades later, O’Brien revealed what happened when the cameras stopped rolling.
“He was pissed. He was really mad. I went to commercial,” O’Brien told Rolling Stone. “He stood up. 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*cking show. He humiliated me in front of everybody.’ He stormed out.”
Though he held to his word for several years, Trump would eventually return to O’Brien’s Late Night—more than a dozen times. In fact, he has the distinction of being one of only a small handful guests to appear on Late Night with David Letterman, The Tonight Show with Jay Leno, Late Show with David Letterman, Late Night with Conan O’Brien, The Tonight Show with Conan O’Brien, Late Night with Jimmy Fallon, and even The Jay Leno Show. He is a veteran of the late night wars if there ever was one.
Trump’s history on late night, though, captures his contradictory relationship with comedy that persists today. Just as Bill Maher, for example, insisted to his audience that Trump can, in fact, take a joke and laugh at himself, the White House Correspondents’ Association has disinvited Amber Ruffin from performing at their dinner this year out of fear she would make too many Trump jokes. What the O’Brien experience seems to show is that Trump is good at taking a joke, when he feels he’s in control.
“Trump’s superpower is constantly believing in the infallibility of Trump,” O’Brien observed in the same Rolling Stone interview. “Humility is a weakness to him.”
Watch Trump’s first appearance with Conan O’Brien at the top of this post.
