Drew Barrymore Dances on ‘Late Show’ Desk, Remembers David Letterman

New York, NY — Drew Barrymore brought her signature flair to the late-night scene during her appearance on “The Late Show with Stephen Colbert” on September 4, 2025. The conversation took a nostalgic turn when they discussed former host David Letterman, who has a memorable history with Barrymore.

In April 1995, at just 20 years old, Barrymore famously flashed Letterman while dancing on his desk for his birthday. During the recent episode, Colbert playfully asked Barrymore why she had never danced on his desk. “I promise you, I don’t,” Colbert said, deflecting the suggestion. “It was just a joke.”

Unfazed, Barrymore decided to take matters into her own hands. She removed her jacket to reveal a white shirt that read “We (heart) Stephen,” before crawling across the desk and dancing. “It’s different now,” Barrymore, now 50, remarked lightheartedly.

Colbert, a bit flustered yet appreciative, embraced Barrymore and said, “You’re the best.” This entertaining moment highlighted Barrymore’s playful spirit, which continues to engage audiences.

In related news, David Letterman is set to appear as a guest on the upcoming sixth season of Barrymore’s daytime talk show. This reunion is expected to bring back nostalgia for fans of the “Late Show” legacy.