The task of defining Madonna’s impact is brutal. You could say she redefined the power of pop stardom. Or helped establish music videos as an art form. Or called her own shots in a career that amounts to living mythology. But that would still be selling Madonna short, since any rote discussion of her “great business skills” leaves out the impact of Madonna as a person -- the impish, unapologetic, philanthropic, often hilarious crusader who has been the LGBTQ community’s raddest pop heroine since she introduced her armpits to a hand dryer in Desperately Seeking Susan.
As far as being an ally goes, she’s the Elizabeth Taylor of pop; as far as iconography goes, she’s like if Marlene Dietrich were an X-Men. That’s a whole lot of gay credibility. Pride Month is not the same without Madonna and her music, and thus we recount 10 of her great gay moments.
1. Those Decades of AIDS Activism
Back in the ‘80s, we were hard up for celebrities who spoke out against AIDS (and it didn’t help that we had a president who was, shall we say, reticent on the subject). But in 1989 Madonna and her Detroit-era dance instructor Christopher Flynn, who was then diagnosed with AIDS, fired up New York with a major benefit dance marathon. By that time, Madonna had already lost her good friend Martin Burgoyne to the epidemic. In footage from the event, she thrashes about with sweet abandon. That’s fun to watch, but it’s even cooler to see Flynn, who later died from the illness, open up about Madonna as a confidante who understood him.
2. The Documentary Where Madonna Is Queen, But the Gays Rule Too
The ‘91 documentary Truth or Dare is quite possibly the second most essential purchase for new Madonna fans after The Immaculate Collection. It gives you legendary performances (not just the masturbation-centric “Like a Virgin” but also “Oh Father,” “Vogue,” and “Keep It Together”), infamous cameos from the likes of Antonio Banderas, Kevin Costner, and then-beau Warren Beatty, plus scream-worthy interactions with her backup dancers, most of whom were gay. Truth or Dare is one of the first documentaries I ever saw that featured gay dudes hanging out. They go to a Pride parade, gossip about each other, and get an earful from Madonna when they’re mean to another dancer. “Be nice to him. He doesn’t have the thick skin that you have,” she intones like the headmistress of homosexuality. Be sure to bring a hanky when she dedicates a show to her pal Keith Haring, who died just before the tour started.
3. Yep: Ellen Came Out With the Help of Madonna
Where were you when you learned Madonna was an instrumental part of Ellen DeGeneres’ coming out? I’m still blown away. Here’s Ellen herself remembering kind words from M.
4. The Drag Tribute That Rocked the ‘99 VMAs
The 1999 MTV Video Music Awards were perfect. You had Lauryn Hill winning Video of the Year, Ricky Martin owning America, Prince introducing TLC, and an amazing tribute to Tupac Shakur and The Notorious B.I.G. by their mothers, Afeni Shakur and Voletta Wallace. You also had a stunning, utterly gay moment in the form of a drag tribute to Madonna’s career. One by one, drag queens toasted her most famous looks: the “Like a Virgin” wedding dress, the “Open Your Heart” cabaret look, the goth “Frozen” gown. Finally Madonna herself came out, patrolled the phalanx of queens, and declared, “All I have to say is it takes a real man to fill my shoes.” Extra special props to the queen in the “Bedtime Story” gear who absolutely annihilated that runway.
5. The Pain of “In This Life”
One of the concluding tracks on Erotica, Madonna’s much-maligned 1992 album that has since earned a major cult following (what kind of monster can’t get into “Deeper and Deeper”?), is an elegy for the singer’s friends who’ve died of AIDS. Her performance is understated and touching, which only serves to highlight what an underrated balladeer she’s always been.
6. “Vogue” Is a One-of-a-Kind Gay Fantasia
Voguing is the hallmark of black and Latin dance balls in Harlem, and there’s always been a debate as to whether Madonna’s “Vogue” fairly samples from that culture. Its legendary video served up both real voguing and stylized non-voguing, and while there are definitely black and Latin dancers performing those moves alongside Madonna, you may question the validity of a white, straight pop star acting as the dance’s unofficial figurehead. Either way, Madonna accomplished something astounding with “Vogue” -- she ushered an audacious, unapologetically queer art form into mainstream America, and that means gays everywhere got to witness (and recognize) a rare kind of performative ebullience. Plus, she got to revel in her serious love of old movie stars.
7. The 50 Million Times She’s Denounced Homophobia
Madonna performs this act just about everywhere. In Russia while Putin looms like a Crisco-drenched albatross? Check. In an English interview way back in the ‘90s? Check. One of the finest: When she donned a Boy Scout uniform at the 2013 GLAAD Awards to present Anderson Cooper with the Vito Russo Award. She mocked the Boy Scouts’ homophobic membership ideals and lamented the fact that she couldn’t get in despite her well-honed ability “to scout for boys.” A few years later on RuPaul’s Drag Race, Bob the Drag Queen would mimic this look and assure us he was the most “prepared” queen of season eight.
8. The Sandra Bernhard Situation
For the better part of 30 years, one of Madonna’s favorite hobbies was annoying David Letterman. She was propelled by his dry humor and always gunned to freak him out live on air. In her first major appearance alongside Dave, she arrived as a surprise guest while friend Sandra Bernhard lit up the stage with her usual sauciness. Everything about this pop culture moment is absurd and unforgettable: the matching jean-shorts, the cheeky implications of a love affair between Madonna and Sandra, and Dave’s befuddlement. The queer rumors would then follow the “gal pals” around for a while, and in 2010 on Wendy Williams’ show, Sandra lamented the end of their friendship. I certainly lament the era when celebrities loved being obnoxious on national television, played by their own rules, and didn’t waste our time with boring on-set anecdotes.
9. Her Amazing Tribute to Her Late Friend, A-list Interior Designer David Collins
After Madonna’s friend David Collins died in 2013, Madonna penned a letter describing his influence on her life. It’s a moving tribute, and it contains one anecdote letting you know what a rad gay pal he was: “He took to calling me Muriel after we saw Muriel’s Wedding, because he said it was sacrilegious and downright ridiculous to say my name in public or private. Did I mention his witty and irreverent sense of humor? Shame on me.” She added: “In my darkest hours (and there were plenty of those) he always managed to say something that made me laugh and stop feeling sorry for myself. He never allowed me to indulge. He would say, ‘Muriel, stop complaining, it doesn't suit you. Let's go to Ibiza!’ And he meant it. He loved going to Ibiza: yes, the gorgeous men; yes, tripping the light fantastic; yes, the occasional tab of X; but most of all he went for the music.”
10. The Greatest Reddit AMA Reply of All Time.
I’m still reeling from Madonna’s single foray into Reddit, an AMA where she answered tons of questions. The best, though: “If you were a gay man, would you be a top or a bottom?” Madonna’s lowercase response: “i am a gay man.”
For more stories about the LGBTQ community and our fiercest allies, follow Billboard Pride on Facebook.