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Madonna: The Queen of Pop’s greatest ever gay moments

As Madonna turns 60, Matt Cain examines the Queen of Pop's unbreakable bond with the LGBT community.

By Will Stroude

All she needs to do is dig out her fishnets and we come running – and from the start of her career gay men have been Madonna’s biggest fans.

When there were no gay role models to look up to, we identified with her as a strong woman defined by her sexuality, a sexuality which, like ours, placed her outside what was considered normal. We empathized with the pain she’d felt going through divorce and the death of her mother and admired her ability to strap on her shield-like corset and get out there to face the world.

And she never failed to stick up for us, making speeches to promote AIDS awareness in the 80s and more recently railing against anti-gay discrimination in Russia and Malawi. 

To explain why so many gay men feel an affinity with the Queen of Pop, here’s a run-down of Madonna’s gayest moments (so far)…

Her formative relationships with ballet teacher Christopher Flynn and New York artist Keith Haring, who both later died of AIDS

In her earliest interviews Madonna credited her gay ballet teacher as being the first person who really understood and inspired her; it was Christopher Flynn who took her to concerts, art galleries and gay clubs and made her believe she could achieve her dreams.

She thanked him when she was inducted into the Rock and Roll Hall of Fame in 2008 and wrote the song ‘In This Life’ about his death from AIDS. ‘In this life,’ she sang, ‘I loved you most of all’.

Madonna became friends with gay graffiti artist Keith Haring when she worked as a coatcheck girl and he was a busboy in legendary New York nightclub Danceteria.

“We were two odd birds in the same environment,” she later said, “And we had the same taste in men.”

Once she became famous she helped promote Haring’s often explicitly gay work, performing ‘Dress You Up’ in an outfit designed by him in 1984 and ‘Into the Groove’ in a Haring-inspired set on her Sticky and Sweet tour.

Her work helped bring gay culture into the mainstream

One of Madonna’s best ever songs and videos was directly inspired by gay culture. ‘Vogue’ paid tribute to the dance craze invented by drag queens on the Harlem ‘house ball’ circuit, which she discovered a few years later in New York’s gay clubs.

If you feel inspired to strike a pose check out the 1990 documentary Paris Is Burning and find out exactly what ignited Madonna’s spark – and later gave life to RuPaul’s Drag Race.

She’s pushed sexual boundaries like no other artist

Much more theatrical than the traditional live gig, Madonna’s Blond Ambition tour changed pop music forever. Highlights included her masturbating with two hermaphrodites and cavorting with her often half-naked male dancers.

When the backstage documentary In Bed With Madonna was released, we discovered six out of the seven dancers were gay and even got to see a close-up of two of them French kissing. In the pre-internet era it was like watching gay porn at the multiplex.

When she helped take the issue of same-sex parenting to the big screen

The Next Best Thing should have been Madonna’s greatest triumph as an actress, appearing opposite Rupert Everett as a yoga instructor who has a baby with her gay best friend. Same-sex parenting may be the new normal now but in 2000 it was a radical idea – and Madonna was the one pushing it into the mainstream.

Unfortunately the film’s a turkey but read Rupert Everett’s autobiography to find out how hard Madonna tried to make it work and how passionately she believed in its message.

When she thrust same-sex kissing down Middle America’s throat

She’d already revelled in the shock-value of same-sex kissing in her video for ‘Justify My Love’ but she took things one step further at the 2003 MTV Music Awards by snogging Britney Spears and Christina Aguilera live on stage.

OK, it was lesbian rather than gay but you just know if Madonna were a man she’d have been up there on stage tonguing Justin Timberlake.

However big she got, she never forgot her gay roots

Confessions on a Dance Floor was one of her best and biggest-selling albums but it was also one of her gayest, drawing influences from disco, ABBA and Donna Summer. So where else could she launch it but at London’s G-A-Y?

Her sensational five-song set still ranks as the brightest moment in the history of the iconic nightclub. Is it too much to hope that she’ll make a return visit to launch her next album? 

Matt Cain is the author of The Madonna of Bolton, out now.