Celebrities Share Their Favorite Stephen Colbert Stories: Robert De Niro, Emma Thompson, Julia Louis-Dreyfus, and More | Vanity Fair
No one knew in the beginning what Stephen Colbert’s Late Show would look like. Back in 2015, most of us knew him as “Stephen Colbert”—the conservative blowhard he’d played for nearly a decade on Comedy Central’s satirical Colbert Report. That brilliant high-wire act cast a long shadow: Could Colbert’s Late Show top his incredible run playing someone else?
Eleven years later, it’s hard to imagine what late night will look like without Colbert. Ever since he took a firm political turn in 2016, Colbert and his team have provided a nightly respite from the chaos of the Trump era. That didn’t stop Paramount and CBS executives from announcing last summer that the show would end after its 2025-2026 season—a move the executives described as “purely” financial despite critics’ furious allegations to the contrary.
As The Late Show and Colbert prepare to sign off on May 21, one reality is inescapable: We’re witnessing the end of an institution. But even in the face of all the political and economic headwinds facing late night, Colbert himself has a reputation for being kind and engaging. As he prepares to sign off the air and embark on his next project—a Lord of the Rings movie, the perfect assignment for a die-hard Tolkien fan—more than a dozen big-name guests and colleagues shared their favorite behind-the-scenes Colbert memories with VF—from potentially disastrous technical difficulties to awkward encounters to heartfelt moments that will stick with them for years to come. The following anecdotes have been lightly edited and condensed for length and clarity.
“At the end of our first show, we’re all celebrating backstage, and Stephen disappears. I don’t know where he goes. I imagine that he’d want to bask in the glory of this, but lo and behold, he’s going to the edit room because he’s a showrunner as well. I’m like, Okay, I’ll catch up with him at the after-party.
“We’re all gonna watch the show air in real time, and everybody’s there. My whole family’s there. His whole family’s there. There’s this huge entourage of friends and family and love, and it’s 15 minutes before the show goes on air, and he’s still not at the party. He’s still in the edit room. The show isn’t exporting. I heard after the fact that they decided to stream live from the editing software instead.
“So Stephen doesn’t come to the party until after the show is on air because he’s in the edit room. He didn’t want to say that to everybody in the party, so he comes in and acts like nothing happened. Everybody’s celebrating, and it’s like the king coming to town. But I knew.”
“I remember the first time I appeared on Stephen’s show I was overwhelmed with adoration. I left the building in a whirl of joy, having written him a fan letter on a cardboard coaster only to find Stephen in my car. My first thought was—thank God! He feels the same. We’re going to run away together and build a new life, featuring many animals from refuges, margaritas, and superb cuisine. But he had only wanted to tell me in person how much he’d enjoyed my visit. That he bothered to do that just before recording another show has always stayed with me. I think he’s still got the coaster.”
“I have a weird thing with Stephen, because I was very close to my mom, who died a long, long time ago, in 2009. She was completely obsessed with Stephen Colbert. I don’t think I’ve ever told him that, because I think that would be weird, but there’s just a really deep affection for him. Going into that theater was always a mind-boggling thing to be able to do.
“The greatest thing about Stephen is his bravery during these times, which is obvious. He’s never been timid. But for me, he’s just a theater guy. On The Late Show, when they’d cut to commercial, we would often have these very long, funny discussions about, like, the trials and tribulations of having to be naked in a play. I just recognize Stephen as a fundamentally kind human being, which some of these comics are not. He only punches up, and that fundamental kindness means a lot to me. I’m a lucky guy. I get way too much attention, and nothing makes me feel more privileged than to go on his show. It just breaks my heart that it can’t continue because of this corporate bullshit.”
“When I first met him, I just wanted to talk to him about building wooden boats. Then we began to send each other plans for kits for building wooden lapstrake rowboats. He’s not running his own shop, but among Americans who can hold their heads up for working with wood, Stephen’s right up there. He makes Fallon look like a clumsy child.
“When I got the news about Stephen’s Lord of the Rings movie, I texted him my congratulations, and I said, ‘What role should I prepare to audition for?’ He replied, saying, ‘How about Bill the pony?’ Which is very funny for us nerds, because Bill the pony is with them, but he’s just their pony. He doesn’t have any lines. I said that I would Andy Serkis the fuck out of that role, so he better get ready for my per diem.”
“One of my favorite moments with Stephen was years back. He asked me to read Donald Trump tweets as Gollum. You’re told what’s going to happen, but not exactly what or how, and that gives it a kind of glorious freshness. It was the first I’d heard [of the ‘covfefe’ tweet]. I was as stunned as everybody else was, probably. It was such a brilliant word, covfefe. ‘Covfefe, precious.’ My wife still reminds me of that word. We use it in our language at home.”
“He’s always so incredibly cool backstage. He always comes to your dressing room and chats with you. Like, really chats with you. That really makes a difference when you come onstage, because you feel connected to him. He’s so chill that you feel relaxed. You don’t feel that little bit of panic. When I did David Letterman, I was so in awe, because I was a young man and he was like a god. I was sweating, and my hands were ice cold. My pits smelled like Campbell’s chicken soup. But Stephen has a disarmingly charming kind of personality. He’s warm, and he’s really interested, and he’s really curious, so that makes you feel like you’re interesting. I’m trying to incorporate that in my life more. Also, Stephen has the best swag. I like the Levain cookies in my dressing room.”
“Stephen and I went down to the San Diego Comic Con together. We hosted this massive thing for Amazon’s The Rings of Power, and watching him correct actors on how to pronounce some of these characters’ names was just [hilarious]. It wasn’t him trying to be mean or snarky. He’s just that enthusiastic.
“The thing which makes it hard for me to tell cool stories is that most of the cool stuff on that show happens onscreen. Jennifer Lawrence and us were just drinking booze and taking off our shoes, and he got kind of tipsy. On a lot of late-night shows, they want to know what remarks you’re going to be making and have it all preplanned. This is confidence that I think Stephen gives both his staff and his guests: You really sense that if anything new happens that day and you want to just talk about it, he’ll just roll with it. He’s unflappable.”
“All of my appearances on The Late Show With Stephen Colbert were memorable to me. I just wish I could remember them. What I do remember are Stephen’s warmth, humanity, intelligence, and humor. No wonder CBS canceled him.”
“My connection with Stephen was so instantaneous—the relief I felt just sitting down with him thinking, Oh, this guy gets it. I truly feel like Stephen is one of my comedy soulmates. But the last time that I went on his show, I was there promoting the documentary about my friend Andrea Gibson, who had recently passed away. Before Stephen brings his guests out, he always comes over to say hello and just kind of connect for a minute. We usually are just silly together, but this time, he really took me by surprise. He came over, grabbed my hand in both of his hands, and just directly and sincerely said, ‘I love you so much.’ I had done a lot of emotional prep before I saw him, and I was in a good space, but then when he came over, my emotions jumped to my throat. I cried trying to get through Andrea’s poem on the show. Even though it seems so tiny, it just really, really stuck with me.”
“Big Mouth, my animated show about puberty, was about to come out, and we tried to do this campaign called ‘#PuberMe.’ I asked the Late Show team, Colbert and company, ‘Hey, I’d kind of love to show a picture of myself at 13. Would Stephen be interested in showing a picture of himself around that age?’ He agreed, and he has a great picture. Then we found out that Mike Bloomberg was also on the show that night, and so Bloomberg found his bar mitzvah picture. This was all happening right around the brutal hurricane in Puerto Rico, Hurricane Maria. So we’re like, maybe there’s a great way to raise money for hurricane relief: have people post a picture of themselves during puberty. We did the show, and then I got on a red-eye to Argentina to go shoot a movie. When I got off the plane, my Twitter and Instagram were blowing up. To Stephen and his whole team’s credit, they were like, ‘Let’s lean into this and get CBS to put up some money.’ We ended up raising a ton of money.”
“There was a day [in the Colbert Report era] when I got an email saying, ‘Would you do a dramatic reading of a press release?’ Newt Gingrich’s presidential campaign was flailing, and they issued this outrageous release about how he stood tall in the midst of all the fury. It was so absurd and made Gingrich look like such a fool—and I found out later that the press release was written by none other than Corey Lewandowski, who was Gingrich’s campaign manager at the time. We rehearsed it for literally 15 seconds, and then, bam, we just did it.
“Stephen never had to sell me on anything. We would just have a wonderful time. All the Rudy Giuliani sketches on The Late Show, with the false teeth and the black hair dye and everything—we’d do brisk run-throughs and then, bam, just do it live. Every single time it absolutely killed. They all were twice as good as we thought they would be. The very first one was uncanny, how beautifully it worked. At a certain point I put on this helmet and tried to drink the wine even though the plastic visor was down. It was completely spur of the moment. It was just great to make Stephen laugh that hard.”
“I’m proud to be in the same class as Stephen, Jimmy [Kimmel], and all the late-night hosts. We keep each other sharp. We’ve always worked well together since back in the Colbert Report days, but I think knowing that we have each other’s backs through any crisis made us closer. It’s nice to know you have a friend out there, and I hope he knows he has one with me.
“On the two times I’ve been on the show, he runs from his desk backstage and gives me a quick hug before I go out, which I’m sure he only does for me. So that makes me feel special.”
“During the very first Melania Trump sketch that we did, I was actually secretly pregnant with my first daughter, Ella, who’s now nine. And then my last sketch that I just did, she and Stephen were watching me together on the monitor. My friend Emily Gertler, who’s the booker on The Late Show, took a picture, and I find it so moving that I have a picture of me and Stephen where I’m like barely pregnant for the first one, and then for the last one, I have this beautiful picture of him looking at my daughter and smiling. So beautiful.
“Ella came to the set with me a lot over the years. I have pictures of her in the Melania wig when she’s, like, 18 months old. All kids go through major separation anxiety, but there was one fitting we had where she literally wouldn’t let me put her down, and so they just fit me into my Melania costume while I was holding her. It was pretty sad to do the last one, but also so special. My parents were there, my husband was there, Ella was there, and my now almost four-year-old was there. It’s really a family there. They became part of my family.”
“Coming into The Late Show, I was such a fan. I thought that The Colbert Report was so ingenious and hilarious every night and ridiculously consistent. I was upset that it was going away, but I was also fascinated to know what he would do with the Late Show format, because I always had this feeling that as wonderful as the show is, this is a man who should have the opportunity to do so many different things with his creativity.
“It’s just a very warm space. I know Stephen a little bit outside of the show, but our kids went to college at the same time at Northwestern, so the day we dropped them off, we all had dinner together, and that felt very special. It couldn’t be more emotional because you’re in the middle of a nervous breakdown. You’re truly melting down and trying to appear like you’re not. Everyone’s hiding the fact they just want to cry the whole time, and then that crying only lasts for like three years.”
“The thing that stands out for me with that was that he was genuinely mystified that The Lord of the Rings wasn’t being given the same treatment as, let’s say, Harry Potter seemed to be that year. He took it as a personal affront.
“The four hobbits flew out to New York, and we caught a show. We asked Stephen where we should go for dinner. There was a restaurant that I think is pretty hard to get into, but Stephen said, ‘Listen, we obviously have a little bit of sway over here on the show, so let us make a few phone calls.’
“We managed to get into this very classy, bougie restaurant, and Billy [Boyd, who played Peregrin “Pippin” Took in the LOTR trilogy] had forgotten his reading glasses. The waiter must have overheard us, so he came over and he had a drawer of reading glasses for Billy to pick from. I think myself and Billy both assumed this would be to look at the menu and give back, but the waiter was like, ‘No, no, those are yours to keep.’ So we walked away with a pair of reading glasses. I think we as a cast all loved the fact that Stephen was so clearly on our side fighting for us. He really wanted us to feel that it was a special experience, and we were treated like kings.”
“Me and the Veep cast filmed a crossover scene with Stephen for The Late Show, and I remember him being very nervous, which I found incredibly endearing. He nailed it, of course, but it was a very bizarre concept, and he is a big Veep fan. I mean, he remembers scenes from the show that I don’t even remember having anything to do with. There may have been a moment where he was sort of screwing up lines, and he was just feeling nervous about getting it right, and I thought that was very sweet.”
“I went on with my buddy Derrick Beckles one time, and we were so nervous that I think Stephen thought we were drunk and trying to prank him or something. It was Derrick’s first time on late night, and I didn’t prepare because I thought I was just there to support Derrick. I drank a ton of caffeine before the interview, and that is a misstep for somebody with stage fright like me. I got this huge boba tea, something I never order, and I drank, like, a gallon of it right before I went out there.
“I basically disassociated. I think Stephen thought I was trying to do some Andy Kaufman shit, but I was actually outside of my body visiting my ancestors in another realm.
“This was right before Stephen wrapped for the summer for vacation, and after a while, he leaned over and whispered, ‘Come on, guys, I gotta get out of here.’ I looked in his eyes and was like, ‘Oh, he’s being sincere.’ They chopped up the interview so drastically. But I remember learning from that experience. Now, instead of caffeine before an interview, I meditate. I have this breathing exercise I do, and then I do a ton of heroin, and I’m ready.”
“I am the preface to his whole solo talk show career. I was in New York, and the publicists had let everybody who might need somebody know that I was in town. We get this call that Stephen Colbert is doing his own show called The Colbert Report over at Comedy Central. They haven’t aired it yet. They’re going to get an audience, and they just need a guest, so you’re kind of the guinea pig. I went down there, and he was so excited, he was bouncing off the ceiling with a huge smile on his face, saying, ‘Whatever I say out there, please don’t take it personally.’
“I went out and sat in the chair, and then, of course, you watch this guy bound across the stage, absorb all the applause for, like, 30 seconds, and then finally sit down. I was already on the floor laughing, and then he proceeded to just make a fool out of me, and that was it. Years later, at his big finale of The Colbert Report when he was about to embark to CBS and take over for Letterman, Stephen brought back all of his favorite guests, and I was one of them, standing there with Jeff Tweedy, Henry Kissinger, Alan Alda, Katie Couric, Big Bird. Stephen doesn’t forget.
“Since then, I’ve been on The Late Show I don’t know how many times. Now that he’s winding down, I can’t share details, but I’m included in one of the final shows. Again, it’s Stephen saying thank you for all those years. That’s who he is.”
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