To celebrate the reigning Queen of Pop and Pride Month, we’re getting into a groove and expressing ourselves with a timeline of Madonna’s celebrated ties to the LGBTQ community. As surely as a proper Madonna greatest hits compilation these days would have to be, say, 75 to 100 tracks or so, it’s impossible to sum up any aspect of her career in one place without a bit of shortchanging. In characteristic Madonna fashion, these are edgy, funny and sexy moments that stand out– as well as some linear context. Here is our look at Madonna’s unique, historic connection to the LGBTQ community.

The early years

Madonna Louise Ciccone was born in Bay City, Michigan in 1958, to a household with seven siblings. She lost her mother to breast cancer in 1963, at the age of five. In the years since she became a global superstar, Madonna has often credited her childhood ballet teacher with encouraging her to pursue her dreams. The following quote is from her 2019 acceptance speech of the GLAAD Media Advocate for Change Award.

The move to New York City 

In 1977 at the age of 19, Madonna moved to New York with 35 dollars in her pocket. She studied dance under the legendary Martha Graham, who gave Madonna the nickname “Madame X.” Madonna’s star as a performer and musician rose amidst the height of AIDS crisis and paranoia. She lost many of her closest mentors, friends and collaborators to the disease–among them her roommate Martin Burgoyne and legendary artist Keith Haring.

Decades of HIV/AIDS activism and advocacy

In years when very little was known about HIV/AIDS, and many called it “gay cancer,” Madonna was ahead of her time, outspoken as to the need for awareness and research. Christopher Flynn was diagnosed with AIDS in the late 1980s, by which point Madonna had become one of the most famous people on the planet. In 1989, the two rocked New York with a benefit dance marathon. Flynn died of AIDS-related complications in 1990. Madonna’s AIDS advocacy work continues to this day, notably via her charity Raising Malawi. March 27, 1990 - “Vogue” is released as a single. “Voguing” is among the most unapologetically queer of art forms, originating from dance balls in Harlem. Madonna sampled it in the David Fincher-directed music video for her smash hit song. Heavy on disco but also cutting-edge with a killer bass line, “Vogue” topped the charts of over 30 countries, becoming the highest-selling single of the year, an indispensable Pride anthem, and one of Madonna’s signature tracks. Say it with us now: The Blond Ambition Tour and Truth or Dare documentary.  Named by Rolling Stone as the concert of the decade, Madonna’s most iconic tour broke box-office records around the globe, also causing headline-grabbing controversy. Following the tour, Madonna released a behind-the-scenes doc called Madonna: Truth or Dare. The frank, funny and unapologetically sexy depiction of real-life homosexuality in the film inspired many people to come out. Released in markets outside the U.S. as In Bed With Madonna, Truth or Dare became the highest-grossing documentary in motion picture history. The Erotica Era  Madonna released her fifth studio album, Erotica, on Oct. 20, 1992. Dark and jazz-infused Erotica was a critical and commercial disappointment upon release, in some ways overshadowed by the release of Madonna’s massively successful Sex book. Today, Erotica is appreciated as one of the very best and most innovative pop records of the 1990s. Its influence is seen in the work of virtually every current pop act: Beyoncé, Lady Gaga, Rihanna, P!nk, Britney Spears, Christina Aguilera, Katy Perry, Years & Years, Ariana Grande, Miley Cyrus, and others. In one of the reviews of its day to get it right, Rolling Stone praised Erotica as “a post-AIDS album about romance.” Also on Erotica: a track called “In This Life” is an elegy for the friends Madonna lost to AIDS. The track samples George Gershwin’s “Prelude No. 2 For Piano,” and it’s a testament to Madonna’s long-underrated balladry. Madonna performed the song in a touching, stripped-down moment on her acclaimed Girlie Show World Tour. 1999 – The Madonna drag queen tribute at the VMAs  The 1999 VMAs was one of the best ever. Lauryn Hill won top honors, Ricky Martin rocked our socks off… and several drag queens dressed in Madonna’s most iconic looks kind of stole the show. At the end of it all, Madonna summed the whole thing up perfectly, saying: November 9, 2005 - Confessions on a Dance Floor and “Like It Or Not” Madonna released her Confessions on a Dance Floor record in late 2005. The all-dance album is arguably her most consistently energetic and thrilling. On one of her most underrated tracks, album closer “Like It Or Not,” Madonna sings a chorus that lends itself beautifully to LGBTQ Pride: It’s a simple chorus, and from a lesser artist it wouldn’t be so special. Delivered with Madonna’s conviction, it feels nothing short of life-affirming. 2008-2009 - Keith Haring tribute on the Sticky & Sweet Tour  Double-dutch jump-roping while wearing hotpants and knee-high socks (defying any haters who’d obsessed over the fact she just turned 50), Madonna paid a special, eye-catching tribute to Keith Haring in a lively “Into the Groove.” To this day, the Sticky & Sweet Tour is the highest-grossing tour by a female artist, the sixth highest-grossing tour of all time. April 20, 2010 - “The Power of Madonna” on Glee  Fox’s high-school musical hit show Glee aired a special dedicated entirely to Madonna and her songbook. The theme of this Emmy-winning episode is the need to respect people of all gender identities. In many ways, it’s a big rainbow flag of an episode, on a show that was ahead of its time in terms of inclusivity. Madonna doesn’t appear on the show, but she voices her approval of it, particularly the choice to have an all-male chorus sing “What It Feels Like For a Girl.” October 2012 - Ellen Says Madonna Helped Her Come Out  Ellen DeGeneres dedicated an entire episode of her talk show to Madonna, who appeared wearing an update of her iconic, structured Jean-Paul Gaultier cone corset, from her MDNA Tour. On the show, DeGeneres dropped a bomb: Madonna was instrumental in her 1997 decision to come out. This is a moving and intimate exchange between two titans. March 16, 2013 - The Anderson Cooper encounter at the GLAAD Awards When presenting the Vito Russo Award to Anderson Cooper at the 2013 GLAAD Media Awards, Madonna appeared dressed as a Cub Scout, to encourage Boy Scouts of America to allow LGBTQ youth to join. In May of that year, BSA announced a resolution for more inclusivity. This funny and heartfelt speech is top-form, terrific Madonna, full of one-liners. Sept. 2013 - Probably the best Reddit AMA response in the history of the internet  Madonna had a highly publicized Reddit Ask Me Anything session with her fans. Any fan can tell you: Madonna is hilarious, so witty and clever. There were a lot of gold nuggets in this laid-back chat (read the whole thing because it’s LOL-funny). The best bit: One Reddit user asked Madonna, “If you were a gay man, would you be a top or a bottom?” Madonna replied, “I am a gay man.” Perfect. Fans rejoiced. Along those lines, check out this vintage interview snippet, a mic-drop. Madonna has taken a stand for people of all sexual orientations roughly one billion times…and that’s just counting the times she was on camera. May 1, 2019 - “I Rise”  Madonna released “I Rise” ahead of her latest album’s release as a Pride anthem. Madame X’s closer, the soaring, muscular ballad samples Parkland survivor Emma Gonzalez’s “We Call BS” speech. At the heart of “I Rise” is much of what’s always been at the heart of Madonna’s artistic output: self-respect, self-love, rebelliousness and defiance– and compassion. May 4, 2019 - The GLAAD Media Advocate for Change Award  Madonna was awarded the GLAAD Media Advocate for Change Award for decades of support of the LGBTQ community. This isn’t an annual award; Madonna is its second-ever recipient, after Bill Clinton. Madonna delivered a speech about her history with the community that brought the audience to their feet. June 7, 2019 - “Dark Ballet”  Madonna released trippy, atmospheric track “Dark Ballet” ahead of Madame X. Sampling Tchaikovsky’s “Nutracker Suite” with a straight-up bananas vocoder bridge, the angry, passionate song really grows on you. The video is a stunner. Gay rapper Mykki Blanco plays Joan of Arc, violently burned alive at the stake. The footage was shot in Madonna’s then-home base of Portugal. June 30, 2019 — WorldPride NYC Madonna performed at New York City’s WorldPride. Not only was this the best news imaginable for New York’s Pride festival; the way Madonna announced it, in a Today exclusive, was oh-so-Madonna. It’s a sweet moment– and totally, utterly theatrical and dramatic. Madonna’s legions of adoring fans would have it no other way. The concert itself was the kind of rousing spectacle we know to expect from the modern master of performance art, with a beguiling ease and sense of humor that’s grown over time. June 24, 2021 — Post-Pandemic Pride Blowout  After weeks of teasing a special Pride-themed event on her socials, Madonna singlehandedly restores New York City nightlife to a post-pandemic world via a jam-packed, hyper-exclusive (Anderson Cooper, Andy Cohen, Zachary Quinto and other celebs were in attendance) charity performance at the Meatpacking District’s Standard Hotel. The same night in Times Square, the Queen of Pop premiered a Pride-themed art film she produced with her tour videographer-turned-trusted personal photographer. The film, and Madonna’s in-person performance, showcase a candy-colored, steampunk new look that calls back the edgy Erotica days with a twist—and razor-sharp dance moves. To say “she’s still got it” is, er, reductive. For nearly four full decades now, Madonna has always been it. July 2021 — Madonna schools DaBaby re: HIV misinformation on social media  Following a headline-grabbing, nauseating homophobic outburst (complete with bogus, offensive remarks about HIV/AIDS) onstage at Rolling Loud Miami, rapper DaBaby is blasted by audiences and some of the biggest names in music—including Elton John and Questlove. Madonna leaves arguably the biggest imprint with a scathing Instagram post directed @dababy: The post has been viewed nearly one million times in under 24 hours. Mic drop! What is your all-time favorite Madonna moment? Is there one you think we should have included here? Sound off in the comments. Gay Pride!

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