Grindr Presents Confessions with Madonna

Although Madonna had already established herself as a gay icon and ally before the release of 1991’s Truth or Dare (which was shot and directed by Alek Keshishian during 1990’s Blond Ambition Tour), it wasn’t until this “rockumentary” arrived in theaters that the pop star cemented herself as the ally to beat. Indeed, it seemed Madonna was the only one amidst a sea of other so-called gay icons who didn’t step up nearly as much as she did when it mattered most (well, save for Elizabeth Taylor). This included, of course, “casting” a troupe of all-gay male dancers for the Blond Ambition Tour. Not only that, but none of her dancers were white—yet another major “fuck you” to the mainstream standards of the time.

As it was for Madonna to show two gay men kissing onscreen. Specifically, Salim “Slam” Gauwloos and Gabriel Trupin (one of three dancers who sued Madonna after the release of Truth or Dare for “invasion of privacy, fraud and deceit, misrepresentation and intentional infliction of emotional distress”). The latter would end up dying of AIDS in 1995, not long after the Truth or Dare lawsuit against Madonna was withdrawn thanks to a settlement (for an undisclosed amount) being reached. So while Trupin might have been angered with Madonna for choosing to share that very intimate moment in her documentary—thereby outing him to the world—in the long run, it can’t be denied that she did turn him into a kind of gay hero. One-half of a duo that would lend potential strength to those who were still too afraid in 1990/1991 to come out of the closet (a term now mostly associated with the thrift store of the same name).

In fact, one could argue that it was not just these two dancers, but all seven of the men who appeared in Truth or Dare that paved the way for the six who appear in a “round table”-like setup with Madonna for Grindr Presents…Confessions with Madonna (a title that also sounds like Truth or Dare’s UK name, In Bed with Madonna). Not just for them to be “themselves” but to be able to speak so freely. Not that Madonna herself has ever felt hemmed in by the “rules” that would dictate otherwise. Joining her as “replacements,” of sorts, for the dancers that helped her blaze the trail for gay rights, visibility and general acceptance are Ivy Mugler (a dancer who joined Madonna on The Celebration Tour), designer Raul Lopez, playwright and now longtime Madonna cohort Jeremy O. Harris, Bob the Drag Queen (who MC’d The Celebration Tour) and Marcelo Gutierrez (who recently became Madonna’s go-to makeup artist).

Once again, it’s no coincidence that Madonna has surrounded herself only with “queer folk.” Not just because the video was made for Grindr, but because, quite simply, Madonna feels freest (to loosely quote her lead single from Confessions II) when she’s amongst gays. Most like “herself.” Which is to say, raunchy and unfiltered without having to worry about pearl-clutching à la her 1994 appearance on the Late Show with David Letterman.

So it is that she commences by telling everyone, “Let’s all be upfront and honest, forthcoming and revealing.” And with that, she gets right into it by asking, “How do we feel about a hole pic?” Needless to say, not everyone is “about it.” Though Madonna is the one to remind those who are averse, “They could be beautiful.” Only Marcelo Gutierrez seems to agree—Jeremy O. Harris less so.

Having broken the ice with that queery, Madonna continues, “Okay, I’ve got a question. When you’re having sex, do you prefer lights on or lights off?” The conversational, “I’m your best friend/Mother”-type tone she has in Truth or Dare has now been well reanimated, likely in no small part thanks to the glass of rosé in front of her (with most everyone else having a different kind of glass with something more vodka-looking inside of it). To be sure, the callback to Truth or Dare during this “confessional” video is underscored not only by the intercut black-and-white shots of the group, but also by one of her “underlings” having the “audacity” to ask her a question. And that person is Mugler, who demands of Madonna, “So…do Italians do it better?” This a reference to the now illustrious shirt M wore during the “Papa Don’t Preach” video. Unfortunately, none of the “clientele” represented in the circle is Italian or of Italian descent, therefore the immediate chorus of a reply is, “No.”

Madonna goes along with it before “receiving” the next question about “what makes a Mother?” (you know, in the gay sense of the word). It’s during this part of the discussion that Madonna meta-ly mentions how, “A lot of people tell me that when they watched Truth of Dare that was the first time they ever saw men kissing.” She then goes on to explain her fierce need to protect members of the gay community during the rise of the AIDS epidemic, telling her circle, “I didn’t feel judged by them.” Bob the Drag Queen replies, “That’s impressive. To not be judged by the judgiest group in the world.” Or maybe Madonna is just immune to being judged, hence breaking down the barrier that would have stayed up between her and the gays had she not been on board with their brash sense of humor (which she herself already had to begin with).

Raul Lopez is then the one to ask, “Who was your best dick down?” (the modern equivalent of Donna De Lory asking, “Who’s been the love of your life your whole life?”). Madonna opts for “diplomacy” by insisting that she’ll only be willing to name dead people. Yet, surprisingly, she doesn’t name 2Pac, instead going for John F. Kennedy Jr. And, undoubtedly, the reason she really seems to be offering him up as her answer likely has less to do with her genuinely feeling that way and more to do with tapping into the zeitgeist of Love Story. After all, Madonna is referentially interwoven throughout the series, so it’s no shock that she would want to reemphasize her proximity to something and someone that’s still currently trending.

To conclude this Truth or Dare redux (courtesy of direction by Nuno Xico in lieu of Keshishian), Madonna commands her friends to make the sound they do when they have an orgasm. Harris then points out that Madonna pioneered an entire “genre” of making orgasm sounds on her records (starting with 1990’s “Justify My Love”). Perhaps just another of the many reasons Madonna transcended into the gay icon she remains today. Even if the younger gays will never truly understand what she did for them. Releasing Truth or Dare included.