Madonna And Sandra Bernhard Were Once BFFs — What Caused Their Falling Out?

In the late '80s and early '90s, Madonna and Sandra Bernhard were tabloid fixtures. Bernhard was an out and proud lesbian, while Madonna had previously been known only for her male conquests. They kept everyone guessing as they were snapped getting cozy and holding hands around town. They even did a joint David Letterman appearance wearing matching outfits and playfully hinting at a romance. "We'd kind of planned to dress alike. I mean, we planned it a little bit," Bernhard told The Hollywood Reporter. "And then, of course, it just went off on its own spontaneous fashion. And yeah, it just became kind of a legendary appearance for both of us."

"She came to my show in 1988, came backstage, and then we started hanging out," Bernhard told Wendy Williams about their first meeting (via Us Weekly). "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 even appeared in the singer's 1991 documentary "Truth or Dare." She drank wine and played Sigmund Freud to an Evian-sipping dream-sharing Madonna. The chemistry between the gap-toothed two proved a stark contrast to that of Madonna and her bewildered-looking then-boyfriend, Warren Beatty. 

One minute the singer and comedian were besties, then, seemingly overnight, Bernhard joined the league of stars who can't stand Madonna. So, what happened? Why did Madonna and Sandra Bernhard go from BFFs to foes without passing frenemies? What caused the falling out?

Madonna's future BFF, Rosie O'Donnell, remembers watching her and Sandra Bernhard during their iconic 1988 David Letterman appearance. O'Donnell admitted on "Hot Takes & Deep Dives" that her first thought was, "How odd is that?" She said she couldn't imagine the two being close as "Madonna was the biggest star in the world." O'Donnell also confessed to suffering friendship FOMO at the time. So, whatever happened to Sandra Bernhard and Madonna's relationship?

The hot couple quickly turned ice cold, something Bernhard said was inevitable when it came to Madonna. The comedian also appeared on "Hot Takes & Deep Dives" to spill the Madge breakup tea. "We went out quite a bit," Bernhard said, admitting she didn't like the same "level of visibility" that Madonna did. "I tried to impart in our friendship, 'I'm really your friend,'" she explained. "Not just somebody who's passing through." The "Roseanne" star said it was "hard for somebody like [Madonna as] she doesn't like somebody who reflects too much of what she is. Therefore her relationships don't last."

Meanwhile, Isaac Mizrahi made a juicy claim about why Madonna and Bernhard really fell out. The fashion designer said they became part of a "love triangle" after "pansexual" Madonna allegedly bedded Bernhard's girlfriend, Ingrid Casares. "The truth is Sandra was betrayed because Madonna had an affair with Ingrid," Mizrahi alleged during an interview on what appears to be the Madge-dishing channel of choice, "Hot Takes & Deep Dives."

Madonna and Sandra Bernhard's friendship was done after they became embroiled in an alleged love triangle. However, Madonna remained close to Ingrid Casares, who Isaac Mizrahi claimed she stole from Bernhard. After the comedian slammed Madonna for her inability to maintain friendships, Casares hit back — hard. "What a liar!! Sandra Bernhard! She wasn't asked to be in the Sex Book and got p*****. (Like the girl who didn't get picked on the dodge-ball team in high school and still holds a resentment) Madonna has had the same friends for over 30 years!" Casares tweeted.

Whatever the real reason, Bernhard has put the drama behind her. "I've seen [Madonna] over the years. We're cool with each other, you know," she told Us Weekly. "People move on, and you have your life. I have a daughter and my girlfriend. I have my career, my life. And, you know, things do change." Bernhard even admitted to listening to "bits and pieces" of Madonna's then-about-to-be-released new album, Madame X.

During a "Watch What Happens Live" appearance, the comedian was asked what she thought about the Lady Gaga and Madonna comparison. She said it was inevitable "when somebody follows in the next generation" and graciously talked up Madonna's "original, edgy, fashion-orientated, dance-orientated, revolutionary" body of work. However, she couldn't resist one last dig. "Didn't they make out on 'SNL' or something?" Bernhard asked. "I'm surprised Lady Gaga's still alive."