For decades now, Madonna has been a true gay icon, even before her music career started. From supporting her gay friends and speaking out about their rights back in the ’80s, to rumors of relationships with women like Sandra Bernhard and Jenny Shimizu, to her close relationships with drag queens and ballroom legends, Madonna has always kept the LGBTQ+ community close to her heart.
Now, as we celebrate her, let’s look back at five of her most memorable moments as a gay icon
1. Her first 'Late Night' appearance
All the way back in 1988, Madonna made her first Late Night appearance as a special, unscheduled guest brought on stage by bisexual comedian Sandra Bernhard. The two wore matching outfits of white t-shirts, blue jean shorts, white socks, and black shoes, and were constantly flirting throughout the appearance.
While host David Letterman tried to interview the two women, they were hanging all over each other, complimenting each other, making inside jokes and double entendres, and teaming up against the Late Night host to talk about their relationship. At one point he asks “what a typical night” is like for the two women and if he could join. Madonna replies with her tongue in her cheek, “Maybe if you got a sex change!”
They also said their evening would end with a stop at the Cubbyhole, a famous lesbian bar in New York City. It’s an iconic interview that started rumors about the two across the world.
2. Advocating for AIDS
Madonna was one of the first notable celebrities to speak out about the AIDS epidemic in the late 1980s. In 1989, she and her first dance instructor Christopher Flynn, a gay man diagnosed with AIDS, held a benefit dance marathon raising money for AIDS Project LA and people who were affected by AIDS.
In a speech at the event, Flynn thanked Madonna. “You will understand the depths of my faith in her when I tell you she was among the first persons I turned to when I was diagnosed,” he said. “She understands, she cares, and like you, she knows that being here makes all the difference.”
“You know, he’s thanking for me being here,” Madonna replied. “But I have to say thank you to him, because he’s the man responsible for encouraging me to go after my dreams, to go to New York. He taught me… I went to my first dance class from him. He’s a great guy.”
Madonna’s “Vogue” is one of the biggest and best pop songs of all time, and it introduced the mainstream to the ballroom culture and dance created by Black and brown trans and gay people.
Madonna was introduced to the voguing style of dance by the drag queens, gay men, and trans people of the House of Xtravaganza in New York. House members Jose Gutierez Xtravaganza and Luis Xtravaganza Camacho choreographed the ballroom dancing in the video and also danced in it and on tour with Madonna. Since then, even the most cis and straight person has known how to vogue.
In a now infamous Reddit Ask Me Anything from 2013, Madonna shook the whole world with a simple answer to a funny question.
“If you were a gay man, would you be a top or a bottom?” one fan asked.
“I am a gay man,” the singer and actor simply replied. Truly iconic.
5. Singing at gay weddings at the Grammys
Yes, looking back on Macklemore’s performance of “Same Love” at the 2014 Grammys was one of the strangest moments in straight allyship, but at the time, it was also one of the most powerful.
That performance included lesbian singer Mary Lambert singing, Queen Latifah (before she confirmed her relationships with women) officiating a mass wedding that included gay couples, and the icon herself Madonna walking on stage singing “Open Your Heart” surprising everyone.
At the time, it was a powerful message for gay marriage, which wouldn’t be made legal in all 50 states until the next year. Having Madonna – a longtime supporter of gay rights and a bi icon herself – show up was the ultimate cherry on top of this gay rights sundae.