Sandra Bernhard reflects on ‘sad’ breakdown of her relationship with former bestie Madonna after mysterious falling-out

Sandra Bernhard confessed that it “really makes me sad” that she and Madonna couldn’t “maintain” their friendship.

The pop star and the comedian became very good friends in the 1980s, when they both performed on stage in New York City.

In a TV moment that became an instant classic, Madonna and Sandra wore matching outfits and flirted with each other on Late Night With David Letterman in 1988.

However, in 1992, their close bond mysteriously disappeared, and rumors have been circulating ever since about the reason.

Now Sandra has fondly reflected on her ‘perfect time’ with Madonna, in an episode of Modern Family star Jesse Tyler Ferguson’s podcast Dinner is on me.

Their friendship began in 1988, when Madonna starred in David Mamet’s Broadway play Speed ​​The Plow.

Meanwhile, Sandra performed in her off-Broadway one-woman show Without You I’m Nothing, which she adapted into a film shortly after.

Now, more than 30 years after their friendship ended, Sandra said she would “love” to meet Madonna again.

“But I mean, I don’t know what it would be, you know? I mean, and I hate to get nostalgic and get stuck in, you know, that time, because it was such a perfect time,” she said, looking back on her life and career in the late ’80s, with her frequent Letterman appearances and her successful stage show.

“There are times when I think, It makes me really sad that we couldn’t keep our friendship going,” she said, adding cryptically, “I mean, I could have.”

Sandra’s good friend, fashion designer Isaac Mizrahi, previously shared his sensational theory that a love triangle had caused her to fall out with Madonna.

Isaac alleged that Sandra was in a relationship with high-profile nightclub owner Ingrid Casares, with whom Madonna subsequently had an ‘affair’.

“I wasn’t sure what Madonna was planning to do with Sandra,” he said on the Hot Takes & In-Depth Dives podcast. ‘I know Madonna is pansexual… and I guess I couldn’t tell what was going on between them. I couldn’t tell if they were having an affair or if Madonna was after Sandra’s friend, who was pretty, a girl named Ingrid.’

Now Sandra has fondly remembered her ‘perfect time’ with Madonna, in an episode of Modern Family star Jesse Tyler Ferguson’s podcast Dinner’s On Me; pictured in 2021

The pop star and the comedian became known as good friends in the 1980s when they both shared the stage in New York City; pictured at the Brooklyn Academy Of Music in 1989

In a TV moment that became an instant classic, Madonna and Sandra wore matching outfits and flirted with each other on Late Night With David Letterman in 1988

However, in 1992 their close bond mysteriously disappeared – and rumors about the reason have been circulating ever since; photo 1991

Ingrid became a successful media figure in the 1990s, surrounded by a host of celebrity friends, including Donald Trump and Tommy Mottola.

She once claimed that Sandra and Madonna had a falling out because Sandra was not asked to be one of the models in Madonna’s Sex book.

However, Isaac disputed Ingrid’s version of events, saying: ‘The truth is that Sandra was betrayed because Madonna had an affair with Ingrid.’

He insisted that Sandra “didn’t give a damn” about the book Sex and he never expressed any desire to be one of the models involved in the project.

“None of us really liked that book,” Isaac said pointedly. “That book was, you know, a little forced, a little contrived.”

Now, more than three decades after their friendship fell apart, Sandra noted that it would be “fine” to see Madonna again; photo from 1991

Sandra’s close friend, fashion designer Isaac Mizrahi, has sensationally claimed that she and Madonna had an alleged love rivalry over Ingrid Casares; Ingrid and Sandra pictured in 1991

When Sandra herself was a guest on the same podcast a year earlier, she was more vague about the end of her friendship with Madonna. She did indicate that the media attention that came with it had become a burden for her.

“I didn’t really like that level of visibility and having to work all the time,” the Roseanne actress said. “We all work at it as performers to some extent, but I’m a very improvisational person, on stage and in my life, and I don’t like being tied down to being a certain way for my image.”

Sandra added: ‘What I try to convey in our friendship is, ‘I really am your friend, I’m not just someone passing through.’

She reflected, “And I think we had a real friendship for a while, but it’s hard for someone like her. She doesn’t really want someone around her that reflects too much of who she is. So her relationships just don’t last.”