Sandra Bernhard Reflects on Her ‘Sad’ Friendship Breakup With Madonna

Sandra Bernhard can’t help but imagine what it would be like to reunite with Madonna nearly 30 years after their friendship breakup.

“It would be fine, but I mean, I don't know what it would be,” Bernhard, 69, shared on the Tuesday, July 30, episode of the “Dinner’s On Me” podcast . “I hate getting nostalgic and caught up in that time because it was such, like, the perfect time.”

Bernhard and Madonna's friendship made headlines in the late '80s. One of their most memorable moments together was when they wore identical outfits during an appearance on Late Night with David Letterman in 1988.

While fans enjoyed observing the pair’s friendship, Bernhard once revealed that they weren't speaking by 1992.

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“The late ‘80s [was] when I was doing my one-woman show here in New York and I was friends with her and doing Letterman all the time,” the comedian recalled in her latest podcast interview with Jesse Tyler Ferguson . “I mean, everything was just so fresh. So there are times when I'm like, ‘That really makes me sad, you know, that we couldn't maintain our friendship.’ I mean, I could have.”

Us Weekly has reached out to Madonna’s reps for comment on Bernhard’s latest remarks.

While it’s unclear why the pair’s bond became strained, the comedian previously shined a light on why they were no longer seen together.

“We would go out. We would have a genuinely great time, and I think we were a really good example of two women being friends,” Bernhard said on The Wendy Williams Show in 2010. “I would have liked that to have gone on for a while [longer]. Certain people can’t handle those kinds of friendships. That’s not my style. I like to maintain my friendships throughout my life. … It’s OK, you know. All is forgiven.”

Years later, Bernhard reiterated that she wasn’t hung up on her relationship with the 65-year-old music superstar. Instead, she chalked it up to the fact that friendships can simply change over time.

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“I’ve seen her over the years,” the Roseanne alum told Us in 2019. “We’re cool with each other, you know. But people move on and you have your life. … I have my career, my life.”

Friendships aside, Bernhard continues to bring the laughs on her standup comedy tours. Earlier this month, the actress announced 10 upcoming tour dates for December. “From West Coast to East,” she wrote via Instagram on Friday, July 26. “Let’s kick it into high gear!”

As for Madonna, she recently concluded her career-spanning Celebration Tour in May with a free concert in Brazil.