Drew Barrymore has always been known for her spontaneity, her charm, and her ability to create unforgettable television moments, and she proved that once again during her latest appearance on The Late Show With Stephen Colbert. Nearly thirty years after her infamous 1995 desk dance on David Letterman’s Late Show, Barrymore decided to recreate the moment, much to the delight of the studio audience and the sheer embarrassment of Colbert. What began as a nostalgic mention of Letterman quickly spiraled into a hilarious, chaotic reenactment that showed Barrymore is still as playful and fearless as ever.
The moment unfolded after Barrymore started reminiscing about her history with the Ed Sullivan Theater, the iconic space where both Letterman and Colbert have filmed their shows. “I mean, I’ve spent some times here with David Letterman in this room,” she said wistfully. Colbert, ever the quick-witted host, replied, “You have. I’m only mildly insulted that you’ve never gotten on the desk.” The line was meant as a joke, but anyone familiar with Barrymore’s personality could have predicted what came next. Without hesitation, she asked, “You want me to do a little dance for you?” Colbert immediately tried to shut it down, insisting, “I promise you, I don’t. It was just a joke.” But Barrymore was already committed to the bit.
With the audience cheering her on, Barrymore dramatically took off her blazer to reveal a customized white button-down shirt. Bedazzled across the back were the words “I ♥ Stephen,” a playful homage to her host for the evening. Removing her shoes, she climbed onto Colbert’s desk as the Late Show Band struck up a groove. The audience erupted into applause while Colbert, visibly flustered, nervously tried to protect his coffee mug from being knocked over as Barrymore began swaying her hips.
Fully leaning into the nostalgia, Barrymore didn’t just dance. She crawled across the desk, playfully reenacting her iconic 1995 performance when she had surprised Letterman by dancing, flashing him, and giving him a birthday kiss. This time, she kept things lighthearted but equally chaotic, grinning at the camera as Colbert buried his face in his hands. At one point, she exclaimed, “It’s different now!” reminding everyone that while the times have changed, her sense of fun has not.
The routine ended with Barrymore stretching out across the desk triumphantly, basking in the audience’s cheers, while Colbert awkwardly sat at his chair behind her, unsure of how to bring the show back to order. After a comedic pause, he quipped, “Well, Drew, I’m afraid that’s all we have time for everybody,” eliciting laughter from the crowd. Then, staying in character, he pretended to examine her like a doctor, placing a hand on her forehead and joking, “And tell me where the pain is, Drew.”
The exchange ended warmly, with Colbert helping Barrymore down from the desk and pulling her into a hug. “You’re the best,” he told her, sealing a moment that will undoubtedly go down as one of the most memorable guest appearances of his tenure.
Barrymore’s recreation carried more weight than simple nostalgia. As she has explained in past interviews, the original desk dance with Letterman was a turning point in her life and career. She hadn’t planned the stunt; it was an impulsive act of freedom. Letterman’s reaction—choosing to treat the moment not as inappropriate but as spontaneous and joyful—set the tone for how audiences remembered it. “David Letterman taught me really, really well,” Barrymore told Entertainment Weekly last year. “If somebody does something spontaneous, you have a real choice to make it uncomfortable or a joyful celebration. He made it okay for everybody in that moment. Certainly me.”
By reprising the moment decades later, Barrymore honored not only her own history but also the spirit of late-night television itself: unpredictable, playful, and slightly irreverent. It was also tinged with a bit of poignancy, as Colbert’s Late Show franchise will officially come to an end at the conclusion of its current season next May. For Barrymore, it may very well have been the last time she ever danced atop the show’s famous desk, making the gesture feel like both a tribute and a farewell.
As the episode wrapped, viewers were left with the same impression Barrymore has carried with her since that first daring moment in 1995 — that the best television happens when hosts and guests embrace spontaneity, allow themselves to be vulnerable, and lean into joy. Nearly thirty years later, Drew Barrymore reminded everyone why she has remained such a beloved figure in entertainment: she knows how to make people laugh, how to surprise them, and how to turn even the simplest joke into a legendary memory.
