Rebel Heart: Madonna’s Most High Profile BFF Breakups And What We Can All Learn From Them

Screen shot 2015-04-10 at 4.12.06 PMSandra Bernhard and Andy Cohen recently sat down to critique Madonna’s latest music video “Ghosttown” on Watch What Happens Live.

Of course, anyone who knows anything is aware that, once upon a time, Madge and Sandy were thick as thieves. Back in the late ’80s and early ’90s, the pair were often spotted running around New York City together, making joint appearances on The David Letterman Show, and, at one point, even rumored to be lesbian lovers.

“She came to my show in 1988, came backstage, and then we started hanging out,” Bernhard told Wendy Williams back in 2010. “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.”

Then one day, that all abruptly ended.

“I like to maintain my friendships,” Bernhard said. “But, you know, certain people can’t handle those kinds of friendships.”

Of course, Sandra Bernhard isn’t the only close confidant Madonna has dropped for seemingly no apparent reason. The rebel heart has a long history of ditching her pals.

Scroll down for some of Madonna’s most high profile BFF breakups…

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Gwyneth Paltrow

There was a period in the mid-2000’s when Madonna and Gwyneth Paltrow were practically joined at the hip. Both were blonde American women living in the U.K. who possessed an air of cultural superiority sophistication. They could frequently be seen gossiping over lunch, working out together, or attending fashion shows, where they snickered at the models from the front row. Then something happened. And now they hate each other.

Rumor has it the falling out occurred when Madonna fired their shared personal trainer, Tracy Anderson, then told Gwyneth she should, too. When Gwyneth refused, Madonna terminated their friendship contract. In 2011, Paltrow alluded to the feud on her blog Goop when she wrote about an “insufferable” friend who left her feeling “drained, empty and belittled.”

The moral of the story: Nobody belittles Gwyneth Paltrow. And absolutely nobody crosses Madonna!

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Niki Haris

Niki Haris sang backup for Madge from 1987 to 2001, appearing in the Who’s That Girl Tour in 1987, Blond Ambition Tour in 1990, The Girlie Show Tour in 1993, and The Drowned World Tour in 2001, as well as in the documentary Truth or Dare, and music videos “Vogue” and “Music.” Then in 2004, she was inexplicably replaced in Madonna’s Re-Invention Tour.

At the time, Haris’s publicist claimed the backup singer had chosen to sit out the tour because she wanted to “focus on her solo career and family,” but insiders said she wasn’t asked to participate after allegedly making off-handed comments about Madge to the press.

In 2009, Haris kinda sorta opened up about what happened, telling an interviewer that “maybe there was some drama” but that ultimately Madonna is “a gem” and she was grateful for having worked with her. “Of course, my ego was involved: ‘Oh, she don’t want me no more!’ But at the end of the day, she gave me the greatest gift,” Haris said.

Unfortunately, these kind words about her former boss still didn’t land her a spot in the 2012 MDNA Tour.

The moral of the story: Once you cross over to the bad side of Madge, there’s no going back.

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Christopher Ciccione

In 2008, Madonna’s younger brother Christopher published a tell-all book called Life With My Sister Madonna. Naturally, the “Keep It Together” songwriter wasn’t pleased.

The gloves came off as Christopher, who had worked with Madonna in a variety of capacities over the course of two decades — from backup dancer, to personal assistant, to interior designer — dished about his complex relationship with his famous sister, her career failures, her marriages, and her lack of boundaries when it came to making money, going so far as to accuse her of exploiting their mother’s death in the documentary Truth or Dare.

The book, which reached #2 on the New York Times Bestseller List, was packed with jabs at Madonna’s age, negative personality traits, parenting skills, and inability to truly love. As a result, the singer didn’t speak to her brother for several years. When asked about the book in an interview recently, she it was “very hurtful” but said she and her brother have since made up.

The moral of the story: Madonna’s not the only member of the Ciccone clan who will do anything for a buck.

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Donna De Lory

Donna De Lory was Madge’s other longtime backup singer, who, like Niki Haris, began working with her in 1987 and appeared in every one of her world tours, as well as several of her music videos, up until 2007. De Lory loyally stood alongside Madonna as she went from pop starlet to music icon to mother to Kabbalist. And that’s when things seemed to go awry for the duo.

“Kabbalah, all of a sudden, was mandatory,” De Lory recalled in a 2013 interview. “I thought it couldn’t hurt, but it wasn’t my belief system per se. However, two times the teacher tied on the red-string, and two times I watched it untie and come off me. They tie these things and knot them and they aren’t supposed to come off for a long time. After it came off two times on its own, I figured that I didn’t need that to protect me.”

Coincidentally, after De Lory decided Kabbalah wasn’t for her, she wasn’t asked back for Lady M’s 2008 Sticky & Sweet Tour.

“Even though she is very wealthy and very famous,” De Lory said, “Madonna is still human and, like all of us, she is trying to figure it all out.”

The moral of the story: Wear the fucking red bracelet!

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Demi Moore

Just like Gwyneth, there was a time when Madonna and Demi Moore were BFFs. When they were younger they’d go nightclubbing together. As they got older they’d go to Kabbalah class together. The women had plenty in common. They both rich. They were both famous. And they both had a taste for younger fellas. But when Demi’s relationship with her younger beau Ashton Kutcher ended, so did her friendship with Madge.

The story goes: Around the time of Ashton and Demi’s split, Ashton signed with Madonna’s long-time manager Guy Oseary. When forced to choose between her relationship with Demi or her business partnership with Guy, Madonna went where the money was and dropped Demi from her Christmas card list.

Talk about getting the shit end of the stick. Poor Demi lost her boyfriend and her best friend all in one fell swoop.

The moral of the story: Money can’t buy you class.

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Liz Smith

So what’s with Madonna ditching all her best buddies anyway? We think iconic celebrity columnist Liz Smith explains it best. In a new interview with The Hollywood Reporter, the 92-year-old veteran reporter opened up about her friendship with Madonna, saying: “She’s an extremely talented, deeply complicated woman. We were close for a while, or as close as anyone can get to her.”

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