If you saw #MissAmerica trending over the last few days that’s because pop powerhouse Taylor Swift dropped her highly-anticipated documentary (which premiered earlier in January at the Sundance Film Festival) on Netflix on Friday. Miss Americana takes us behind-the-scenes and shows the multiple Grammy-winner grappling with whether to voice her political opinions, revealing her battle with an eating disorder, and generally struggling to come into her own as she nears her 30th birthday. It’s required viewing for any Swiftie, but in the pantheon of pop culture docs (and there have been many, Gaga: Five Foot Two, Beyonce: Life is But a Dream, Katy Perry: Part of Me just to name a few) there is one that, nearly 30 years after it premiered, remains the gold standard of the genre. And that, my friends, is Madonna: Truth or Dare.
To give some context, Madonna: Truth or Dare debuted at the 1991 Cannes Film Festival, a festival which has premiered projects from prestigious filmmakers like Lars von Trier, David Lynch, Frances Ford Coppola, and Martin Scorsese. In 1991, Madonna was coming off the massive success of one of her biggest releases, her fourth studio album, Like a Prayer which produced several singles including the feminist anthem/ode to self-love, “Express Yourself,” as well as “Cherish,” “Oh Father,” and of course, the album’s title track, the video for which made worldwide headlines for featuring Catholic iconography like burning crosses and stigmata. The video was so controversial it prompted the Vatican to condemn it and Pepsi to cancel Madonna’s multi-million-dollar sponsorship contract. Before cancel culture was a thing, Pepsi canceled Madonna. But in true Madonna fashion, the mistress of media manipulation only used the outrage to her advantage, becoming even more of a global superstar and pop culture phenomenon. Also, around this time, Madonna had appeared in the movie Dick Tracy alongside Warren Beatty and contributed songs to a soundtrack called I’m Breathless which featured what would become one her most iconic hits, “Vogue,” which produced an equally iconic music video. This is all to say, the woman was at the absolute top of her game. Madonna was Queen of the World and we commoners were merely living within it.
The Like a Prayer and I’m Breathless albums spawned a blockbuster world tour: The Blond Ambition Tour consisting of 57 shows across three different continents. It was on this tour that director Alek Keshishian tagged along, filming footage that would ultimately become the Truth or Dare documentary. Keshishian was no stranger to working with musicians, having directed stylized music videos for artists like Bobby Brown, Taylor Dayne, and Elton John, but Truth or Dare would be his first full-length film. The project was originally supposed to be a straight up concert film (the stage show was certainly interesting, innovative, and entertaining enough to warrant a feature) but Keshishian soon realized the backstage shenanigans were just as, if not more entertaining than the concert footage.
The end result was pure magic. An historic snapshot of a moment in time. A pop culture phenomenon that has often been replicated (see the aforementioned efforts from artists like Beyonce, Lady Gaga, and Katy Perry) but never truly duplicated.
First of all, while most pop stars present a carefully curated image of themselves in these behind-the-scenes type projects, in Truth or Dare, Madonna shows you the good, the bad, the ugly. And while it may be just as carefully-curated as a Taylor Swift documentary, you get the sense that Madonna really didn’t give a f*ck if you liked her or not, unlike many pop stars of today who rely so heavily on being liked and avoiding controversy. Truth or Dare features Madonna being a total brat at times, even shading fellow celebrities like Belinda Carlisle, Oprah Winfrey, and Janet Jackson. And she viciously murders Kevin Coster backstage at one of her shows, sticking her fingers down her throat and pretending to vomit after he calls her show, “neat.” This is Dances With Wolves era Kevin Costner! Oscar-winner Kevin Coster! And she eviscerates him. “Anyone who says my show is neat has to go,” she says on camera.
And who, dear reader, can forget when she came for Toronto. The doc includes scenes where members of the Toronto Police Service show up to the SkyDome at Madonna’s third and final Toronto stop, threatening to arrest the singer on obscenity charges over complaints received about her show being racy and lewd. Madonna, positively gleeful at the thought of being arrested, refuses to back down or change her show in any way. Of course Madonna wasn’t charged but not before dragging Toronto to filth. Long before Drake christened Canada’s largest city “The 6ix” Madonna coined her own nickname, referring to the Ontario capital as “the fascist state of Toronto.” One of the officers portrayed in the scene told the Canadian Press years later, “We were portrayed as being real knobs, if you will.”
Name a modern day pop star at the height of her fame who would allow herself to be filmed showing how she performs fellatio on a bottle, or who would reveal on camera that her ex-husband (in Madonna’s case, Sean Penn, who she divorced a couple years earlier) was the one true love of her life? And remember when she told us about her two-year crush on Antonio Banderas? And when, upon finally meeting him, is super inconvenienced that he’s married, saying, on camera, while seated next to Antonio, “I’ve been wanting to meet Antonio for years. I finally get to meet him and he’s married. That’s of life’s little f*ckovers” WITHIN EARSHOT of his first wife, Spanish actress Ana Leza. Taylor Swift would never! Beyonce wouldn’t dare!
Some parts of the documentary admittedly haven’t aged well, particularly when Madonna literally laughs off her makeup artist reporting being sexually assaulted the night before. One can only imagine how, if released now in a post #MeToo world, how that scene would have got Madonna DRAGGED (and rightfully so) on Twitter.
But more than anything, Truth or Dare was a harbinger of things to come. Long before reality shows, social media and our current era of documenting every little thing we do in our “pics or it didn’t happen” society, Madonna, as she has been so many times before, was steps ahead of us, putting it all out there before putting it all out there was ever a thing. Warren Beatty perhaps, says it best when, bewildered at why his then-girlfriend would let cameras capture her every move, says, “this is crazy, no one talks about this on film? The insanity of doing this all on a documentary?” When someone then asks Madonna if she wants to talk off camera, Beatty retorts, “She doesn’t want to live off camera. There’s nothing to say off camera. Why would you say something if it’s off camera? What point is there existing?” Prophetic.