She doesn’t have to clean up the hotel room. You usually don’t get to spend time in luxury French hotel suites like this one unless you’re rich and megafamous, and when you get to be that rich and megafamous, you have plenty of people to clean up your messes. But the woman in the robe is still picking up the champagne flutes, pushing a tray of ice buckets into the corner, quietly tidying up the aftermath of a celebration. She’s talking about fear and anxiety and how last week, she was convinced she was having a nervous breakdown in Spain. The lights go out, she lays her weary head to rest, and the camera lingers on her, capturing what feels like an extremely vulnerable moment.
It’s August of 1990. Instagram will not be invented for another 20 years, and TMZ won’t slouch toward Bethlehem for another 15. Twitter is not even a gleam in Jack Dorsey’s eye yet. In this late-Mesozoic era of celebrity culture, the curating of a famous person’s image is still outsourced, publicity is still a commodity, and privacy is still a bargaining chip. But this woman, a bona fide pop star who’s allowing someone to film her while she opens up directly to the camera and throws away empty Heineken bottles and sleeps? Bitch, she’s Madonna. And as was characteristic with everything else the singer/dancer/cultural icon had a well-manicured hand in, she’s gleefully rewriting the rules of the game in real time.
A tour chronicle, a time capsule and a template, Madonna: Truth or Dare announced itself as something different the moment it premiered on May 10th, 1991. What started as an idea to shoot a few of her Blonde Ambition shows ended up becoming the blueprint for how to inject performative candor into pop-music documentaries — it doesn’t pull back the curtain on the backstage tantrums, the blood-sweat-tears hard work or the bitchy celebrity encounters so much as integrate them into the spectacle you’re seeing onstage. It’s all one big Madonna-drama-rama. And yet you still feel like you’re getting a portrait of an artist as a control freak that feels uniquely raw, semi-filtered, off-book if not off-camera. This is pop stardom as provocation verité. They should’ve called it Truth *and* Dare.
The backstory has now become Her Madge-esty lore: Having seen filmmaker Alex Keshishian’s Harvard thesis (a pop-fueled take on Wuthering Heights), Madonna requests a meeting. They hit it off. He’s hired to shoot concert footage and some behind-the-scenes tidbits for a possible special on the upcoming tour, and is quickly whisked off to Japan. While there, he begins interviewing the show’s dancers, a hodgepodge of European, Asian, Hispanic and African-American men who are as integral to the stage show as the musicians. Because he can only pin them down to talk in the morning after they’ve come home from a night of post-performance partying, Keshishian conducts most of their interviews in bed.
He realizes that he’s getting good stuff here. Ditto the backstage and after-hours exchanges. After showing Madonna some of what he’s shot, he pitches a pivot to something bigger, broader, more intimate than a concert movie. She agrees, and despite the protestations of her management, allows him and his crew to keep the cameras rolling longer after the house lights have gone up. You want to shoot Madonna reciting fart poems to her makeup artists, and tearing stage managers a new asshole over faulty monitors, and having an awkward exchange with her her dad after he’s witnessed her humping a bed onstage? Here’s your all-access pass, Alex.
The end result remains a tantalizing mix of performance footage and Madonna-after-dark shenanigans, steely professionalism and NSFW personal fretting. This is Madonna you tend to think of when you think of her: the post-bracelets-and-lace blonde bombshell, all sinew and Gaultier corsets. (We stan the Cabaret droog look as well. ) But thirty years later, it practically plays like a greatest-hits album of private moments turned into pop-cultural touchstones: The water bottle. Kevin Costner calling the show “neat.” The Toronto cops turning “Like a Virgin” into a first-amendment Rubicon. The same-sex kiss. Blatantly flirting with Antonio Banderas. (The real hero of this doc? Antonio Banderas’ infinitely tolerant wife.) The montage of Madonna goofing around with her dancers between the sheets. The Pride parade. The clucking over a story involving an affair with the troupe’s one self-identified straight dancer. Warren Freakin’ Beatty.
Everyone remembers Beatty’s great deathblow send-off — “She doesn’t want to live off-camera, much less talk…. Why say something if it’s off-camera? What point is there existing?” — but his real highlight arguably comes before that, when he’s watching the backstage circus blow through Madonna’s dressing room. As he watches her take her makeup off, he stands silently behind, hands on her shoulders. He stares straight into the camera and by extension, at the crew filming the whole encounter. And then he smiles and, with perfect movie-star timing, shakes his head. This is a man who has been famous for decades, and he doesn’t understand why someone would want their most mundane or messy exchanges captured for an audience. Madonna can’t understand why you wouldn’t give that to the public — shouldn’t a peek behind the curtain be a perk you control?
This is how fame would be handled and managed in the 21st century, a sort of direct exchange between fan and artist. Mystique would be replaced by relatability, and Truth or Dare turns the whole celebrity thing into a balancing act. Madonna — she’s just like you, folks. She gets angry and depressed and occasionally has an off night. And also, don’t you wish you were hanging out with her and having these fabulous, once-in-a-lifetime experiences reserved for the stratospherically famous too?
Truth or Dare remains groundbreaking in so many ways, from its gamble on showcasing what happens when people stop being nice and start getting real, to its depiction of gay life — a decade after AIDS began decimating the community, almost a decade before Will & Grace started selling it to the mainstream. It’s the way Madonna is writing her own warts-and-all narrative here that makes this the single most influential music documentary since Dylan’s Don’t Look Back, however. Everyone from Beyoncé to Bieber to Billie Eilish would attempt to replicate its mixture of brutal, behind-the-scenes honesty and big-tent showmanship — you don’t get Queen Bey admitting she’s insecure as she’s inches away from a camcorder or a depressed Katy Perry sobbing before a show without Madge showing them how it’s done.
The difference is that few of today’s pop stars have the confidence or bravery to trust someone outside their team to capture a truth that isn’t vetted or micromanaged to death. After a 25th anniversary screening at the Museum of Modern Art (which Madonna herself allegedly crashed for a brief second), Keshishian admitted that he’d been approached over the years by numerous big-name musicians who claimed to want the full Truth or Dare treatment. He’d film for a week with carte blanche, he said, then cut together what he had. “’Well, we don’t want you to use that part, and I don’t want you to show me doing this.’ I’d say to [their] management, ‘There’s no movie here.’”
There are too many layers to go through now, Keshishian said. With Truth or Dare, he essentially needed Madonna’s sign-off, and that was it. What she said was what they did, a stressed-out Liz Rosenberg and Freddy DeMann be damned. And what she wanted was something close to a gorgeously shot version of the ugly truth, 24 frames per second. She got it, or at the very least, one hell of a legend to print. Madonna always loved to take chances and push boundaries. This documentary was a gamble that, 30 years later, is still paying off.