Examining the Politics of Madonna's 'Truth or Dare,' 30 Years Later

Thirty years ago this month, Madonna: Truth or Dare was released to much fanfare. The documentary—part concert movie, part backstage exposé—captured the singer’s 1990 Blond Ambition world tour. It would be the highest grossing documentary of all time for the next 12 years.

Today, Truth or Dare stands as a feminist moment awkwardly sandwiched between its second and third waves. At the same time, the movie is probably most remembered for its strides toward gay visibility. The film presented Madonna’s touring crew as one big, (usually) happy family. And because all but one of her dancers were gay, same-sex relationships were presented in the film as just the same as everyone else’s. In 1991, in the midst of the AIDS crisis, the impact of that cannot be overstated.

It wasn’t just Madonna’s relationships with her dancers, either. At one genuinely vulnerable point, she is seen dedicating a concert to her friend Keith Haring, who had recently lost his life to AIDS-related complications. Later, we see her lunching with her friend Sandra Bernhard, as the two casually discuss the woman Bernhard is sleeping with.

As one of the biggest pop stars in the world at the time, Madonna’s example mattered. She knew it, and so did Alek Keshishian, her 26-year-old director. “I was in this bubble where that was just all accepted,” Keshishian told the New York Times in 2016. “I felt instinctively that I wanted to get across how in Madonna’s world, homosexuality was just a fact of life. These dancers, who she felt so close to, they were going through that age of AIDS. There was still so much stigma against it. I felt personally the power of putting that out, but I had no idea that it might resonate with others quite the way it did.”

In 2016, Huffington Post‘s Daryl Deino wrote about the impact Truth or Dare had on him as a closeted young man in Skokie, Illinois.

[There] was a scene of a gay pride parade—something I had never seen before … Madonna’s dancers stand in the sidelines while people march, screaming, ‘We’re here. We’re queer. Get used to it!‘ There are all types of people … ‘Even I could fit in there,’ I thought. That moment changed my life … Madonna’s dancers were now my heroes. They let me know that it was okay to be different. Even if you are a part of the LGBT community, you wouldn’t understand what I felt unless you lived through the ‘80s or early ‘90s as a teenager.

It’s important to acknowledge in 2021 just how crucial the documentary was at the time. Because for audiences watching now who didn’t live through the era, there is much in Truth or Dare to be offended by.

For one, the movie is riddled with gay slurs. It’s impossible not to flinch now, watching Madonna drop so many ‘F’ bombs. At one point, she tells one of her dancers, “I wouldn’t hire fags that hate women. I kill fags that hate women. In fact, I kill anybody who hates women.” Cringeworthy though it is, the scene is a reflection of the ‘90s as a period of reclaiming historically hostile language, and a reminder that allies at the time were permitted to do the same. (By the end of the decade, even the ladies of Sex and the City were using the other ‘F’ word.)

That outburst is especially tough to sit through after scenes in which the one straight dancer Madonna has hired appears to hate gay men. “It’s my first time working with fags,” Oliver Crumes tells the camera. “Have you ever seen [dancer] Luis [Camacho] walk in his underwear in front of just a whole bunch of people? I don’t have no kind of respect for these people. We know he’s a fag, or gay, or whatever you wanna call it. But you don’t have to show it to everybody.”

Crumes recently admitted to Vulture: “Before the tour started, I was homophobic. I wasn’t all with it. Learning from all the guys what their lives were like when they were young was just mind-blowing. If it wasn’t for Madonna and that tour, I would never have got that experience.”

In the same interview, backing vocalist Donna DeLory stands by the movie as one that empowers women. “My daughter is 18,” she says, “and in this day and age, she watches that movie and sees nothing but strength. She sees a role model. To be around a woman like Madonna was just like, ‘Yes!’ We felt taken care of.”

It’s true that, for the most part, the Madonna we see in Truth or Dare is powerful, always in control, and astoundingly disciplined with her work ethic. She goes far above and beyond the 21st century idea of leaning in. But the way she handles a sexual assault, mid-tour, is jaw-dropping to witness in the post-#MeToo age. After one of her makeup artists, Sharon Gault, is attacked in New York City, the only member of the crew who seems appropriately concerned is dancer Carlton Wilborn.

“She was at the club dancing,” Wilborn tells Madonna, backstage. “The next thing she knew was that she woke up in her room nude, and her stuff was stolen, and she went to the bathroom and her butt was bleeding.” Madonna responds by covering her face, nervously laughing, then offering an explainer.

“I don’t know how you wouldn’t remember something like that,” she says. “They drugged her ass. All I can think of is that she started talking about how she was on tour with me, she’s staying at the Ritz Carlton and those guys, whoever they were, got it in their mind that they were going to fuck with her.”

Juxtaposed with the scene between Madonna and Wilborn is one in which Gault relays her experience. “I never thought that something like that would ever happen to me,” a visibly shellshocked Gault tells DeLory and fellow backing vocalist, Niki Haris. “It was a nice club. It was really nice. And there were nice people there, and I was dancing with these boys. I was totally sober … And then next thing I know, I wake up this morning. I’m never going to go out by myself again.”

At no point does anyone attempt to contact police, or the club at which Gault was drugged, or get medical or therapeutic assistance for her. The assault is treated as simply a hazard of being naive in New York City, and a particularly harsh life lesson. For anyone still wondering why so many of Harvey Weinstein’s and Bill Cosby’s accusers didn’t come forward sooner, this moment in Truth or Dare stands as an efficient explainer.

The legacy of Truth or Dare is further complicated by the fact that three dancers—Crumes, Gabriel Trupin and Kevin Stea—sued Madonna in 1992 over the film, in part, for invasion of privacy. The three had not wanted certain scenes included in the film, and felt they had not been adequately compensated for their contributions. The case was settled out of court in 1994. This year, Stea told Vulture, “The choice I made to do the lawsuit was literally because I said, ‘What would she do? She would fight for herself’ … She kept telling me, ‘Don’t let people take advantage of you.’”

When all is said and done, Truth or Dare may not be perfect, but it is a perfect snapshot of early 1990s culture, messy though it was. Its status as a groundbreaking work of both female and LGBT empowerment is certainly warranted, despite how 2021 audiences might react to the language and attitudes caught on camera. That three of the dancers featured—Wilborn, Trupin and Salim Gauwloos— were, unbeknownst to audiences, living with HIV or AIDS at the time of filming only serves to give the film added poignancy. (San Francisco resident Trupin died just five years after appearing in Truth or Dare.)

“Alek’s particular vision really paid tribute to gay culture,” dancer Kevin Stea noted this year. “Being gay himself and sharing the humanity of our community is what gave this movie long-lasting legs, and power, and iconic status.”