Sandra Bernhard reflects on wanting to 'shock people' with iconic Letterman joke about having sex with Madonna

Sandra Bernhard is reflecting on a particularly colorful ray of light in her career as a comedian.

The 69-year-old and comedian Judy Gold appeared Thursday on The View to discuss their new Netflix documentary Outstanding: A Comedy Revolution, which examines the history of LGBTQIA+ stand-up comedy in pop culture. During the interview, cohost Sara Haines brought up one of Bernhard's most memorable TV moments, which saw Bernhard and legendary performer Madonna appear on a 1988 episode of Late Night With David Letterman to discuss going to the Cubbyhole lesbian bar in New York City and joke about having a sexual encounter.

Bernhard told Haines that she didn't expect the moment to have as much of an impact as it did. "We didn’t do it for any other reasons other than we wanted to come out and shock people and be crazy," Bernhard said of the exchange, which also included Bernhard and Madonna dressed in matching outfits to speak with Letterman.

Gold, 61, added that the appearance had a huge impact on her as both a comedian and as a young queer person watching at home.

“These two? That was such an iconic moment because it was so dangerous, that moment was like a wink to us, like, I got you," she said. "We’re going to get there.”

"I’m glad that’s how it was perceived," Bernhard, who is bisexual, told Gold. "But, for me, I always wanted to break the norms and really shake people up. I couldn’t imagine being any other way. Doing straight comedy was just too boring.”

On Letterman, Bernhard joked that Madonna was a "much better" lover than Sean Penn, Madonna's husband at the time, prompting Madonna to fall back in her chair and laugh.

Bernhard and Madonna remained friends throughout the '80s, though they reportedly drifted apart in subsequent years.

"I don’t know how she is now," Bernhard said. "She might be exactly the same. I don’t know. But nobody’s the same because we have children. Life changes you. But at that time, it was the right time for our friendship."

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"I mean, it’s sort of hard to talk about it 30 years later. But I can tell you that when we were friends 30 years ago, it was a completely different time. And she was a much different person. I mean, I don’t know how she is now," Bernhard told The Hollywood Reporter in 2021. "She might be exactly the same. I don’t know. But nobody’s the same because we have children. Life changes you. But at that time, it was the right time for our friendship."

Outstanding is now streaming on Netflix.