The story behind Drew Barrymore's flashy 'Late Show' birthday gift to David Letterman 25 years ago

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·Senior Writer, Yahoo Entertainment
·5 min read
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NEW YORK - APRIL 12: Drew Barrymore turns to the audience after flashing host David Letterman during the April 12, 1995 taping of the Late Show with David Letterman in New York City. This show was taped on Dave's Birthday. This photo is provided by CBS from the Late Show with David Letterman photo archive. (Photo by Alan Singer/CBS via Getty Images)
Drew Barrymore after flashing David Letterman during The Late Show With David Letterman in 1995. (Alan Singer/CBS via Getty Images)

On April 12, David Letterman will celebrate his 73rd birthday with his family, far away from the bright lights and empty streets of a quarantined New York City. That’s a far cry from how the retired late night legend rang in age 48 a quarter century ago in 1995. That night, Letterman was behind his desk in Manhattan’s legendary Ed Sullivan Theater hosting a Late Show With David Letterman lineup that included Al Franken, Plácido Domingo Jr. ... and Drew Barrymore. Not that anyone remembers who the other guests were 25 years later — that night belonged solely to Barrymore. Midway through the interview, the actress climbed up on Letterman’s desk and flashed the host to the cheers of the crowd and the befuddled shock of the birthday boy. The moment was instantly enshrined not only in Late Show history, but also in late night television history.

Barrymore’s Late Show appearance came in the middle of a busy year for the former child star, who had celebrated her 20th birthday in February. That same month saw the release of the much-loved Boys on the Side, with Mad Love and Batman Forever waiting in the wings in May and June, respectively. Letterman began the interview talking about her birthday, asking whether she enjoyed it. “It was the first birthday in my whole life that I actually enjoyed,” Barrymore replied, adding that her usual birthday routine was to “sit in the bathtub and cry” due to the nausea-inducing prospect of being the center of attention. For her 20th birthday, she enjoyed a night out at a restaurant with close friends and family, feeling nothing but “good energy.”

Letterman then asked his guest about her other rumored birthday activity: swinging by a New York club called the Blue Angel, which she described as a “nude performance dance art place.” According to reports at the time, Barrymore — who had also posed nude for the January 1995 issue of Playboy — had performed her own striptease for Blue Angel patrons. “Did you do that?” Letterman asked. “Yeah, I did. Why not? Think about it: It’s fun, it’s liberating, it’s free!” Barrymore went on to explain the specifics of the routine: Her friend Jon Rosen played Dick Haney, the world’s funniest comedian. “But the whole joke is he’s actually so bad,” she said. “I’m Lolita, and I come out there...”

At that point, Barrymore decided to show Letterman exactly what Lolita does. “Would you like me to do a dance for you?” she said, before asking Late Show bandleader Paul Shaffer to provide her with a mood-setting soundtrack. Then she climbed up on the desk, swayed her hips, twirled around ... and then quickly lifted her shirt. “I would’ve only done it, but it was your birthday,” Barrymore said when she sat back down, looking alternately elated and embarrassed. “I can’t thank you enough for that,” Letterman replied, before cutting to commercial. “I’m telling you, it was something!”

Barrymore’s striptease wasn’t seen just in the Ed Sullivan Theater: Visitors to Times Square watched it happen in real time on a Sony JumboTron, and, of course, viewers around the world saw it in their own homes that evening. That appearance proved a touchstone moment for the rest of Letterman’s Late Show tenure, which ended 20 years later in 2015, appearing on virtually every “Best of” list written about the show. Speaking with Entertainment Weekly before Letterman’s retirement, Barrymore credited the host for turning what could have been a disastrous moment into the beginning of a beautiful onscreen partnership. “It was scary,” she said, flashing back to her impulsive choice to climb up on his desk. But when Letterman thanked her, he immediately put her at ease. “From the moment I went on — especially with my little dance number, which was completely spontaneous and not calculated in any way — he let the audience know it was OK. He was so accepting of me, and letting everyone know to just go on the ride.”

And the two joked about the moment often whenever she came by the Late Show over the years. During a 2007 appearance right before her 32nd birthday, he asked, “Is there a chance you might do anything like that again?” Barrymore gently turned him down: “Turning 32, I think I’m not a different person ’cause I’m certainly, you know, as wild and free-spirited as ever, but I’m just really glad I had that opportunity and got that out of my system.”

Even after Letterman’s retirement, Barrymore is regularly asked about her choice of birthday present. Two years ago while promoting her Netflix series, Santa Clarita Diet, she stopped by the Ed Sullivan Theater for her first appearance alongside new Late Show host Stephen Colbert. “In this very theater, I did something in particular with Mr. Letterman,” she said. “I sometimes think, that doesn’t feel like me. It’s like a distant memory that just doesn’t seem like me. But it is me, and that’s kind of cool. I’m still down with that!”

And speaking with Access Live in 2019, the mother of two gave her past self a high five. “I’m literally like, a nun now,” she said, laughing. “[David] was super-cool. He allowed everybody to enjoy that moment and he set the tone on an absolute whimsical impulse of mine. Together we were great partners in crime in that moment because neither of us knew what was happening!”

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