Witnessing Flynn also helped Madonna appreciate that there was something different about her younger brother, Christopher. “It wasn’t something I could articulate; it was just something instinctual that I noticed,” she recalls. “My brother always had a lot of girls around him that seemed like they were madly in love with him, but he didn’t seem like he was madly in love with them. And then I saw him interacting with my ballet teacher, and in my mind I unconsciously went, Oh, I get it. I didn’t ask my brother if he was gay. I didn’t even know there was a phrase ‘gay.’ I just understood that they were different. There was some silent, unspoken understanding that they had a connection.”
After dropping out of the University of Michigan and moving to New York City to dance with Alvin Ailey, Madonna Louise Ciccone would be surrounded by gay men, eventually including art-world figures such as the painter Keith Haring. Her immersion in the New York gay community became so complete that she began to wish that she were gay. “I felt kind of left out,” she says. “I didn’t feel like straight men understood me. They just wanted to have sex with me. Gay men understood me, and I felt comfortable around them. There was only that one problem, which is that they didn’t want to have sex with me! So…conundrum! I was like, ‘How am I ever going to get a date? Maybe if I cut my hair and I lose a lot of weight, someone will mistake me for a guy and ask me out.’ ”
Over the first decade of her career, as Madonna began her journey to superstardom, her public association with gay men grew deeper and deeper. When she vaulted onto the world stage in 1982, hell-bent on sacrilege and desecration, most of the U.S. was a wasteland of sexual repression. Pregnancy outside of marriage was taboo. Masturbation was shameful. In a number of states, oral and anal sex were criminal offenses, even if you were straight and married. Strict codes governed the content of television and comic books. Many of Madonna’s raunchy interventions have come to seem less shocking over time: Today, any 11-year-old with an Internet connection can browse an exhaustive menu of sexual options without purpose or planning and nurture a budding deviance with HD video; in the early ’90s, hours of strategizing were required to glimpse so much as a same-sex kiss. The path of least resistance — the one that provided a dusting of plausible deniability for the gay-curious — typically involved one of several Madonna-related options: springing for a VHS copy of her racy video for “Justify My Love,” which was banned by MTV; renting Truth or Dare, the astonishingly gay, astonishingly beautiful backstage documentary of Madonna’s Blond Ambition Tour; or combing through Madonna’s Sex book, still the best-selling coffee-table book of all time and one of the very few places in the pre-Internet era where a person was likely to behold a woman licking a man’s ass.
In 1990, at the height of what might be called Madonna’s “gay period,” she released the video for her Harlem ballroom–inspired “Vogue” and shot the footage for Truth or Dare, which included shots of a gay Pride march, a moment of silence for those lost to AIDS, and bed-and-pajama make-out sessions between gay boys and their den mother. Until 2002, when it was displaced by Michael Moore’s Bowling for Columbine, the film was the highest-grossing documentary of all time, a fact that may bewilder future historians, since it centers on the relationship between a rich white lady and a coterie of multiracial, homosexual dancers.
Truth or Dare prefigured reality television, setting a standard for infinite transparency and mandatory exposure of intimate moments that public figures are increasingly expected to embrace. In many ways, though, the original remains unmatched. As a portrait of a mirthful, liberated band of co-conspirators on a working vacation — the film’s director, Alek Keshishian, called the tour’s backstage vibe “Fellini-esque” and described Madonna as “the matriarch in a circus” — Truth or Dare is far more revealing than its more recent imitators, which include Taylor Swift’s Journey to Fearless, Katy Perry’s Part of Me, Beyoncé’s Life Is but a Dream, and Madonna’s own woeful 2005 follow-up, I’m Going to Tell You a Secret, which purports to track her Re-Invention Tour, but actually focuses on her unhappy marriage to Guy Ritchie.
Truth or Dare may have been too far ahead of its time. Months after the film’s release, three of the dancers, unnerved by the exposure of their intimate lives to the world, sued Madonna for invasion of privacy and “intentional infliction of emotional distress.”
The suit was settled in 1994 for an undisclosed amount, and suggests the extent to which Madonna’s relationship with the gay community has often seesawed between intense mutual admiration and uneasy suspicion. Unlike Joan of Arc, who, in Madonna’s telling, made a mistake in entrusting her life to a gay man who failed to protect her, Madonna has long been sensitive to the possibility of gay betrayal. “I wouldn’t hire fags that hate women,” she announced in Truth or Dare. “I kill fags that hate women. In fact, I kill anybody who hates women.” Madonna’s declaration is 24 years old, but it was only a few months ago that Rose McGowan was burned at the virtual stake for calling out gay misogyny. True, McGowan did not help her cause with the taunting assertion that gays had “fought for the right to stand on top of a float wearing an orange Speedo and take Molly,” but then, neither did she threaten anyone’s life, in jest or otherwise.