Just Turned 60, We Recap Madonna’s 10 Gayest Moments

From Madonna's book, Sex with photographer Steven Meisel.

She’s been denounced by The Pope, called “disgusting” by Donald Trump, and dated Michael Jackson! Madonna has outlived her critics and, ultimately, had the last laugh. As the former Material Girl now self-proclaimed soccer mum of six celebrates her 60th year, we relive the gayest moments from the Queen Of Reinvention’s not-very-like-a-virgin-at-all life.


1 Gay Kisses!

After her American Life album stiffed in 2003 Madonna needed to pull something special out of the hat to win the masses back. At that year’s MTV Video Music Awards she certainly managed it. With then teen idols Britney Spears and Christina Aguilera flanking her, they romped in slutty wedding dresses through a rendition of Hollywood before she tongue kissed them both. The world was never quite the same again.


2 Gay Ambition!

1990’s Blond Ambition (note the masculine version of “blonde”) tour was the moment Madonna transcended from pop star to entertainer. With simulated sex scenes with her mostly gay dance squad, and The Pope denouncing her show, and it remains her tour de force. That all the backstage action, gay kisses as well, was captured on her In Bed With Madonna/Truth or Dare doco movie only helped to cement that reputation.


3 Gay Sex!

A day after 1992’s Erotica album was released, Madonna unleashed her first book, Sex. Working with photographer Steven Meisel they put Madonna’s erotic fantasies in print (hanging out at a club with gay porn stars, kissing daddies, piercing with lesbians – and this was just the tame stuff) and the book sold out. The subsequent anti-Sex mainstream backlash took Madonna’s career half a decade to recover from.


3 Gay Vogueing!

Originally intended as just a B-side, the hit potential of Vogue, ripped directly from the gay house scene, was luckily spotted early on. A lavish B&W video featuring her Blond Ambition dancers striking poses as if they were at a NYC vogueing ballroom contest shot this song to #1 and turned it into a million seller. Madonna even rapped, successfully, about old Hollywood and those “ladies with an attitude” too.


5 Gay Sailors!

The 1980s were tough times for gay men. The only portrayals of gay life you saw on TV or film were either sinister or sad. AIDS was ravaging the community and everyone wore Calvin Klein underpants. In the 1986 video for her Open Your Heart hit, Madonna played a dancer/stripper at a video bar and amongst her paying audience were two strapping Navy hunks draped all over each other. Minor visibility at last!


6 Gay Tribute!

Another of those lost to AIDS, graffiti artist Keith Haring was one of Madonna’s earliest NYC buddies back when she was still a struggling wannabe. She wore one of his outfits for her Dress You Up song on her 1985 Virgin tour, then in 2009 performed a tribute to him on her Sticky & Sweet tour, making Into The Groove all about his artwork. On 2015’s Rebel Heart album, she name-checked him on Graffiti Heart.


6 Gay Drama!

The Next Best Thing had a gay actor (Rupert Everett), a gay icon (Mads) and a gay director (John Schlesinger), yet somehow this 2000 rom-com about a gay man and his bestie who have a baby together was a huge disaster, critically and at the box office. The director’s boyfriend even wrote a letter afterwards chiding Mads and Rupe for the film flopping. Rupert devoted a whole bitchy chapter to it in his biography. Ouch.


7 Gay Brother!

In her early years, Madonna’s gay brother Christopher Ciccone was right by her side. See him dancing with her on Holiday (Top Of The Pops in 1984, pictured) and Lucky Star on YouTube. He progressed to becoming her creative director on the Blond Ambition tour, but when she started to date “homophobe” Guy Ritchie it all got ugly. Chris penned a poison autobiography, with the subtle title of Life With My Sister Madonna, but the two have apparently since kissed and made up. Gay drama in the family!


8 Gay Messages!

In 1989 Madonna was at the top of her game – her Like A Prayer single topped the charts, despite its controversial black Jesus video and her new, more personal album was garnering the best reviews of her career. Just to prove she could put her money where her mouth was, every copy of that album came with a small leaflet asking for compassion and support for AIDS sufferers. That she also fragranced each copy of the album with her then favourite scent, patchouli, only made us adore her more.


9 Gay Divas!

The music world’s ultimate diva playing the political world’s ultimate diva? Beating out both Meryl Streep and Michelle Pfeiffer, Madonna became Evita in the 1996 movie version of the Andrew Lloyd Webber/Tim Rice musical. Not only that but she was pregnant while making it and kept that a secret, too. The new mom picked up a Golden Globe for Best Actress in 1997 and managed to turn Evita’s show stopping ballad Don’t Cry For Me Argentina into a Latin-influenced gay dance club hit.


10 Gay Bars (And Pride)

Zipping up her boots and going back to her roots for her 2005 Confessions On A Dance Floor album, Madonna performed a five song set at London’s aptly-named G-A-Y that’s still talked about to this day. Madonna definitely still loves her gays. In a post to celebrate Pride this year she, “bows down to every Gay Boy that taught me a new dance, how to dress, how to drag, how to slay. To stand tall in the face of adversity, to not give up hope, to own my inner-bitch and to love my flaws!”

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