On January 22, 2010, after less than eight months, Conan O’Brien ended his run as host of The Tonight Show—a headline-generating saga built on executive maneuvering, press statements, media punchlines, and a whole lot of frustration for the comedy legend. He earned loads of support and goodwill in the months that followed, including a particularly moving—and hilarious—gift from Robin Williams, whom O’Brien considered “the best talk show guest in the world.”
But before we get to that, let’s set the stage by unpacking the talk-show drama. O’Brien had hosted his version of Late Night from 1993 to 2009, and he’d already been named Jay Leno’s Tonight Show successor back in 2004. NBC initially gave Leno a new program, The Jay Leno Show, at an earlier time slot, but they decided to move him back to 11:35 p.m., which would require bumping O’Brien a half-hour later. Refusing to take part in this experiment, O’Brien agreed to an exit deal with the network, and Leno resuming his old Tonight Show duties—until the latter passed the baton to Jimmy Fallon in 2014. After staging a 30-date comedy tour, O’Brien created a brand new TBS show, Conan, which ran for 11 seasons starting in late 2010.
Even though his career clearly survived just fine, the experience was still rattling for O’Brien, who considered hosting The Tonight Show a lifelong dream. As he recalled years later, Williams’ kind but unexpected gesture helped lift his spirits.
“I was lucky enough to have some great interactions with Robin Williams before he passed [in 2014],” O’Brien recalled in a 2024 episode of his podcast Conan O’Brien Needs a Friend. “And one of the most memorable examples to me of his kindness is when I went through my whole Tonight Show debacle. Finally, the show is done, and I don’t know if I have a career anymore. What am I going to do next?…I’m lying on the floor in the living room of my house, and the phone rings. I pick it up, and it’s Robin Williams.”
O’Brien, unsure how Williams even got his phone number, was surprised but delighted. “I’ll never forget—he goes, ‘How are you holding up, chief?’ I said, ‘Oh, Robin, thanks so much for calling.’ He said, ‘Listen, you’re gonna be fine. You’re gonna be great. I know you like to ride bikes.’ Because he was really into bicycling…’Go down to the bike shop down in Santa Monica. I want you to go down there. I’ve set up a bike for you.’ I said, ‘What?’ He said, ‘No, no, no. Just head down there. Ride around, and you’ll feel better.’…He said, ‘I told them to paint it in all these crazy Irish colors.’”
O’Brien also told the bike story on Conan during a tribute segment following Williams’ death, saying the gift exemplified both his “generosity” and “amazing spirit of fun.”
“[It] was the most absurd bicycle you’ve ever seen,” he said. “It was bright orange and bright green, and it had shamrocks on it…I didn’t know him well enough to justify this kind of [gesture]…so I called him up and said, ‘Robin, I’m floored by this bike.’ All he would say is, ‘Well, I know you love to ride and you could use it.’ He went, ‘Does it look ridiculous? Does it really look ridiculous?’ I said, “Yeah, it looks ridiculous.’ He went, ‘Good. Do you really look stupid riding it?’ I said, ‘Yeah, I’m gonna look really stupid.’ He’s like, ‘Well, that’s good then!’”
“We know now that he had his battles,” O’Brien added, “and I think it’s particularly courageous for someone to be that generous of spirit in the face of that kind of depression. Such a lovely, special man.”
There are tons of stories out there about Robin Williams enriching people’s lives—from the time he bonded with a grieving gorilla named Koko to his fleeting but life-changing interaction with a struggling stand-up comedian after she bombed onstage. “[A]s the tears came anyway, she looked up and lo and behold, there was Robin Williams,” wrote Cecily Knobler for Upworthy. “She stuttered, ‘You. Are. One of my favorites. Ever.’ He looked at her, his blue eyes warmly crinkling and said, ‘You were amazing.’ It hadn’t been true. But the fact that he would go out of his way to make this total stranger’s awful night into one of her best at that time, was just the kind of person Robin was.”
