Madonna’s Most Lesbian Moments

Today is Madonna’s 55th birthday and this time last year, a video was going around the internet of Nicki Minaj kissing the legend after singing her happy birthday. Of course that isn’t the first time we’ve seen Madge go a little gay. In fact, the performer has been a friend to lesbians throughout her career.

Madonna In Tie

Out club owner Ingrid Casares is one of Madonna’s close friends. She’s dated both k. d. lang, and Sandra Bernhard (another former gal pal of Madonna’s) and was featured in Madge’s infamous book SEX kissing the star.

The Beat Goes On Concert Benefitting LIFEbeat

From a 2012 New York Magazine profile of Ingrid:

She started dating Sandra Bernhard (whom she’d met backstage at Bernhard’s one-woman show in Miami the year before). Bernhard took Casares to Madonna’s birthday party, where Madonna was “very nice to me. She was polite and interested in what I had to say.”

“When I shot the Sex book with her,” says Casares. “We realized we had a lot in common and liked to go running, and that’s where we kind of bonded.” Queer-gossip legend has it that Madonna stole Casares from Bernhard, and that Bernhard felt betrayed. Whatever happened, Casares and Madonna remain estranged from Bernhard.  … Finally, she arrives at this: “I’ve always had a theory that you meet people to meet other people. I met Sandra because I was supposed to meet M. It’s very obvious.”

Holyfield v. Tyson II

"Off the Street" Citizens' Commitee for Children of New York Presented by Chanel - September 12, 1991

Before falling out with Sandra, Madonna and the out comic performed together and were rumored to be lovers themselves. (Sandra later said, “I didn’t sleep with Madonna. We were pulling everybody’s chains, creating a media frenzy. We were friends.”)

Madonna and Sandra Bernhard at the Rainforest Benefit, May 1988

Perhaps the most famous Sapphic performance she gave was the threeway MTV Movie Awards kiss with Britney Spears and Christina Aguilera.

2003 MTV Video Music Awards - Show

2003 MTV Video Music Awards - Show

Madonna has been friends with Rosie O’Donnell for years, too. They have always been platonic.

"Lotsa De Casha" by Madonna Book Party at Bergdorf Goodman - Inside

Madonna and Rosie O'Donnell

And in the ’90s, Jenny Shimizu was a gal pal, too. (The model one said Madonna treated her like “a sex slave. I was her secret ‘booty call’ available any time of the day or night for secret sex sessions.”)


But much of Madge’s sexual ambiguity is performance it seems, as she loves to use girl-on-girlness just as much as she likes to engage in faux sexual circumstances with male dancers. It’s all a part of her challenge on American ideals of sexuality, purity and gender. As far as how she’s identified herself sexually, Madonna told The Advocate in 1991:

I think everybody has a bisexual nature. That’s my theory. I could be wrong.

She also said she’d had a lot of crushes but had “only been in love with men.” One of those crushes: k.d. lang.

There’s K.D. Lang, who’s gorgeous, by the way. She looks like Sean [Penn]. I met her, and I thought, Oh my God, she’s the female version of Sean. I could fall in love with her.


For the record, k.d. said nothing ever happened:

“[Madonna] never came on to me, that was a lot of publicity because we had the same publicist and it helped Madonna and it helped me. I don’t think Madonna ever really liked me, to be honest. We’re very different people.”

But Madonna has a theory about why lesbians have always been so attracted to her:

“I think gay women would want to claim me as their own because I am a really strong woman. I am assertive in a way that a lot of gay women are, and I could be a really good mascot for them or spokesperson or something.”

More than 20 years later, we have some other mascots but Madonna will always be someone who helped spark the conversation about sexuality. And for that we thank you, Material Girl.