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Madonna's 10 Gayest Moments

Madonna's 10 Gayest Moments


Madonna's queer fans know she's always had a rebel heart -- and a love of all things queer.

On the heels of her hotly anticipated 13th studio album Rebel Heart, Madonna's LGBT fans take a look back at 10 times the sexually enlightened singer made our own rebel hearts flutter by showcasing homoeroticism in live performances, music videos, her own life (allegedly!), and let's not forget -- in the pages of that naughty coffee table tome, Sex.

Starting way back in the 1980s, Madonna has been giving visibility to LGBT eroticism, and making the world a sexier place for everybody.

10. The "Vogue" video.
Madonna has explored so much muscled male beauty in her videos, with 1990's "Vogue" being a highlight. She famously cribbed "voguing" itself from gay black and Latino dance halls (see: Paris Is Burning), delivered it to the masses and caused an international sensation. Directed by future-Academy Award-winning film director David Fincher, the video is a gorgeous B&W work of art. Stylistically, it's a valentine to the Golden Age of Hollywood with Madonna and the boys recreating well-known photographs by famed shutterbug Horst P. Horst. Many of the hunky dancers would later appear on Madonna's Blond Ambition tour and in the Truth or Dare documentary.

9. The "Express Yourself" video
Even hotter, 1989's "Express Yourself" video, also directed by Fincher, features a butched-up Madonna, buff dudes, a futuristic set, and S&M imagery galore. Basically the clip is Tom of Finland meets Fritz Lang's Metropolis, and it's sexy as hell. MTV must have agreed: the channel aired it every hour for three weeks after it premiered. Bonus: ladies, remember this marks one of the first times we've seen suit-wearing, crotch-grabbing Madonna? It marks the only time we've seen her crawl on the ground toward a bowl of milk.

Madonna-grindr2-x633_08. Promoting Rebel Heart on Grindr
Was it a stroke of genius or crass commercialism to market Rebel Heart on the gay hookup app Grindr? The girl knows her fans!

Madonna-x633_07. The (alleged!) affairs with model Ingrid Casares, Sandra Bernhard, and model Jenny Shimizu
Stunning model Jenny Shimizu (above right), the woman who famously dated Angelina Jolie in the early 1990s, told interviewers that she and Madonna met up for sex many times before Madonna married Guy Ritchie.

Lesbians of a certain age also remember that model Ingrid Casares (above left) was an early 1990s item with comedian and Madonna pal Sandra Bernhard until she met Madonna to film photographs for the coffee table book, Sex (more on that later). After that, Casares was spotted on the town with Madonna and Madonna only. Lesbian lore has it that the two ran off together. Whatever happened, it ended Madonna's friendship with comedian Bernhard. Casares, who is still a close friend of Madonna's, helped encourage speculation when she told New York magazine in 2012, "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."

6. The "Girl Gone Wild" video
Madonna returned to hot, hunky guys for 2012's "Girl Gone Wild" video. Back in B&W and featuring plenty of boys behaving queerly, the video is pretty much a throwback to the early 1990s when Madonna most enjoyed tantalizing fans with that sort of thing.

5. The onstage kiss with Britney and Christina
The 2003 MTV Video Music Awards reminded the world of Madonna's canny ability to get the world talking. Poor Christina didn't have her lip-lock featured as much as Britney's, partly because a witty camera guy put his lens on a shocked Justin Timberlake so the world could spy as he watched his famous ex make out with the Queen of Pop.

4. The entire Girlie Show tour
Another jump back to the early '90s, but it's worth it, particularly if you are the kind of fan who relishes watching Madonna dressed as Marlene Dietrich and acting lasciviously with her lady back-up dancers. She spanks them, kisses them, fondles them and more in 1993's Madonna Live Down Under: The Girlie Show, which was first broadcast on HBO. Watch the clip and see how the singer transformed "Bye, Bye Baby" into a lesbian burlesque show.

3. The Sex book
Still a shocker to see, but even more so in the fall of 1992 when our country was not yet out of the Reagan-Bush years. The Sex book was filled with beautiful, softcore photographs by Steven Meisel and videographer Fabien Baron (the text though, was mostly ridiculous). Boys-with-boys, girls-with-girls, S&M imagery, and perhaps most shockingly, Madonna with Vanilla Ice.

2. The "Erotica" video
In which fans first meet gold-toothed Dita, our mistress for the night, the persona that narrates Madonna's fifth studio album, Erotica, released in tandem with the Sex book in 1992. Shot on grainy Super-8 film by Fabien Baron, the video features kinky Dita/Madonna exploring hot hijinks with girls and boys. The clip was way too nasty for MTV and the channel yanked it after just three late-night airings.

1. The "Justify My Love" video
The 1990 video for "Justify My Love" marks the first time MTV banned Madonna, and it famously marks the first time fans got to see the singer in a same-sex kiss, and with an androgynous dominatrix to boot! Lenny Kravitz and Ingrid Chavez wrote the steamy tri-hop tune, but Madonna made it all her own. The surreal video, directed by Jean-Baptiste Mondino (who also directed 1986's "Open Your Heart video) features those same beautiful Blond Ambition dancers, as well as Madonna's then boyfriend Tony Ward. One of the most controversial videos of all-time. Deservedly so.

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