Cybill Shepherd once showed up on David Letterman's show in just a towel — and things got awkward
Cybil Shepherd has always been known for her boldness, but nothing quite compares to the time she refused to wear clothes during an incredibly awkward interview with David Letterman. This bizarre moment in late-night television history took place in 1986, when Shepherd, then at the peak of her fame thanks to ‘Moonlighting,’ strolled onto the 'Late Night with David Letterman' stage wearing nothing but a towel. The audience gasped as Letterman, never one to shy away from an awkward moment, greeted his guest with the question, "What exactly do we have here?" Shepherd, unbothered, responded with a smirk, "What's it look like?" Letterman jokingly said, "It looks like you in a towel."
As per The Things, Letterman further presses her, "Why exactly did you choose to come out like that? Not that we don't love it and appreciate it." As it turned out, Shepherd’s towel-wearing stunt was not a publicity grab but a response to an ongoing joke Letterman had been playing for weeks. Hanging in the background of the talk show set was an elegant green outfit, which, according to Letterman had been sent to the studio by someone from Shepherd’s team. Letterman explained, "And they sent it to us and we hung it up there and it's been here all week...We thought it was a little strange that they sent it out so we just hung it up there and never. I don't even know if we even referred to it during the last couple of weeks. But I'm glad your clothing is here and I'm glad you're here certainly." Shepherd jokingly quipped, "When I heard that you had had it there all week, it sort of, I sort of didn't want to wear it anymore... I didn't know what you'd done with it while it was hanging there."
The interview took an even more uncomfortable turn when Letterman started discussing Shepherd’s history of on-screen nudity. He asked her about the movies she had done without clothes. To which, Shepherd quickly corrected him and noted she had only done one movie like that. When Letterman pressed for details, Shepherd confirmed it was ‘The Last Picture Show,' a statement that immediately prompted a male audience member to yell, whether it was available to watch at home. The interaction soon veered into even more personal territory as Letterman touched on Shepherd’s relationship with Bruce Willis, her 'Moonlighting' co-star.
Throughout it all, Shepherd maintained her composure, turning the awkwardness into an iconic television moment that has continued to be discussed for decades. She remarked, “Before I ever did psychotherapy or analysis I did interviews and talk shows, which are a kind of therapy. I mean, you’re talking about yourself, and it does bring about some possibilities of thinking about who you are and where you are in your life.” Even years later, the 'Los Angeles Times' referenced the interview, "Who would be most likely to have on Cybill Shepherd and interview her while she was wearing only a towel? Letterman."
As per reports, Shepherd’s uncanny ability to create uncomfortable yet unforgettable television moments was on display once again in 2007 during an awkward backstage interaction with Madonna on the ‘Today Show.’ As Madonna and host Meredith Vieira made their way outside, Shepherd excitedly approached her, exclaiming, "It's Cybill Shepherd. It's Cybill Shepherd. It's Cybill Shepherd!" Madonna, seemingly caught off guard, gave a quick peck on Shepherd’s cheek and walked away, leaving many to speculate whether she even recognized the legendary actress.