In the Class of … series, Nick Rogers takes a monthly look back at films celebrating their 20th or 30th anniversary of initial release this year — seven from 1991 (the extra in a forthcoming double-feature column) and six from 2001. The self-imposed rules of the column: No films with an Oscar nomination and no films among their year’s top-10 box-office grossers.
The age appropriateness of Olivia Rodrigo is a meme. Carly Rae Jepsen is a Pitchfork darling. Miley Cyrus pals with the Flaming Lips. Lady Gaga has funneled through so many phases she practically belongs to “the olds” now. Teens weaned on Beyoncé are, like her, almost 40.
Whither Madonna in the current era? From a purely musical perspective, she’s guest vocaling with Dua Lipa. But what about her cultural cachet? If today’s young listeners investigated the material girl after hearing their grandmas and grandpas moon over her, would they think she’s cool and righteously keeping the sex in sexagenarian … or just a crazy bathtub Insta lady rambling about her COVID antibodies and posting gross pics of bloody syringes and gauze?
At 62, Madonna is releasing more sonically adventurous music than ever, albeit with nary a radio imprint. She’ll allegedly soon join the ranks of pop stars with musical biopics. Like any shrewd entrepreneur, she’s almost certainly timing at least one more farewell tour to such a film’s release. It’s undeniable that more mammoth moments await Madonna, and perhaps they will harken back to the inescapable cultural vice-grip she held during the 1980s and 1990s.
Pop-star peaks and valleys are tales as old as time. Come 2050, Madonna will almost certainly still be alive and people will invoke this pop-star biblicism about Rihanna, Selena Gomez, Demi Lovato, Taylor Swift, Adele and likely every one of the other aforementioned singers. They are all living in the spotlight, too, some even the subjects of their own documentaries. But spotlights in a prominently online celebrity world are much smaller. Corners are carved out for everyone and consumers can curate their experience. Low on Lovato? You’ll never know a thing about her. Sick of Swift? Mute the right words. Not even the biggest among these singers will ever command the every-waking-moment attention afforded Madonna in her heyday, an omniscience captured with then convention-shattering display in 1991’s Madonna: Truth or Dare.
Conceived as a glitzy chronicle of Madonna’s herculean 1990 Blond Ambition World Tour, Truth or Dare transformed into something else entirely once the entertainer and director Alek Keshishian put their heads together. There is still plenty of slick stage footage to showcase the global spectacle of Madonna’s giant-coned bras, loose-limbed go-all-night dancing and purposeful provocation. It was a tour saved from defeat after Pepsi pulled sponsorship following religious uproar over Madonna’s “Like a Prayer” video, which featured stigmata imagery, burning crosses and Madonna kissing a Black saint. Screw the soda jerks. Madonna did it her way.
Spanning nearly five dozen shows around the world in five months, the Blond Ambition Tour represented Madonna at a total-package pinnacle of glamazonian girlboss. She made no bones about backing vocal tracks on brisk dance numbers like “Express Yourself” because she could sell anything to anyone. Stepping right past the sacrilegious claims, this Catholic icon funneled ideas of penance and transfiguration into the tour’s intimate, interpretive choreography. She took Canada’s threat of arrest for public indecency as an invitation to grind her genitals on stage even more vigorously. She embraced and endorsed omnisexuality with Omnimax spectacle.
But the most enduring appeal and aesthetic of Truth or Dare comes from Madonna’s black-and-white monologues, direct-address confessionals that became constants amid the ensuing decade’s reality-TV boom. Most of the movie finds Madonna lazing in hotels, looking back on her past or even just laying into Warren Beatty, then her lover, who winds up establishing a thematic linchpin to the whole endeavor.
Here, Beatty is the guy who finds himself at a high school prom two years after graduation and instantaneously regrets the decision upon walking into the room. It’s hard to understate the hilarity of every bit that involves the Hollywood legend who escalated his relationship with Madonna beyond director and co-star after they made 1990’s Dick Tracy. Behind the scenes, Beatty offered blocking notes for songs Madonna performed on tour from the film’s tie-in album, I’m Breathless. On screen, he waits out her tantrums about sound glitches and industry suits in the front rows of her shows. He nods in agreement with every attempt to soothe the savage beast. He offers no response when Madonna calls him a “pussy man” who smells bad. At one point, she even relays the delight she finds in having a dream where she embarrasses him.
By the time of the film’s release, Madonna and Beatty were no longer lovers. There is also no footage of any Dick Tracy song in the film, reflecting how both Madonna, and the world in general, had moved on from that movie by then. (The closest it comes is a brief backstage reunion with Madonna, Beatty, Al Pacino and Mandy Patinkin.) Not only did Beatty disapprove of Truth or Dare after a rough-cut screening at his home, he sent Madonna’s attorney a letter demanding that certain scenes be cut at the risk of a lawsuit. They allegedly came to a private agreement in which the scenes in question were removed, and this presaged the film’s protracted legal battles from other corners that would come later.
There remain plenty of scenes in which Beatty silently squirms, including his observation of Madonna’s exhaustive throat exam when her voice is about to go and force the postponement of performances. At first, Beatty cannot conceive why in the world she’d want to get that on camera. But then it dawns on him, with a moonshot revelation that very much seems like the beginning of their end, that she needs it to be on camera.
Truth or Dare was initially planned as a concert special on HBO. When David Fincher, director of several Madonna music videos, dropped out, Madonna contacted Keshishian, whose career she had been following unbeknownst to the filmmaker. Himself a music-video director (albeit not for Madonna), Keshishian traveled to Japan to shoot backstage footage as B-roll to complement concert sequences and latched onto an entirely different idea. He wanted to explore the “Fellini-esque dysfunctional family” Madonna had forged with her backup dancers and vocalists — a dynamic in which she felt a need to be the mother and be mothered. When financiers flinched at that notion, Madonna backed Keshishian’s vision and fronted the $4 million herself.
Placing cameras behind one-way mirrors, Keshishian directed his crew to dress in black and forbade them from interacting with anyone. They’d also arrive at locations early to establish wallflower presence in the room before turning on cameras. The list of what they captured includes all manner of iconic music-documentary moments: comic bits like Madonna’s gag-finger gesture to dismiss Kevin Costner from a backstage party after he calls her show “neat”; explicit expressions of her fellatio technique on a bottle; a melancholy and mournful visit to her mother’s gravesite. Barry Alexander Brown, who had edited Do the Right Thing for Spike Lee and would become one of his closest collaborators, whittled nearly 200 hours of footage down into roughly two. The grainy 16-millimeter results purposefully recall the grubbiness of respective documentaries Don’t Look Back and Rattle and Hum. But where those concerned artistic decisions, identities or explorations relative to the music Bob Dylan and U2 were making, Truth or Dare is more about Madonna’s reconciliation with the persona she’s created — a line to split artifice from reality that, like most things Madonna, is drawn with easily smudged mascara.
Start with that oft-maligned cemetery visit. Accept as a given the implicit artifice imposed by any camera crew, no matter how far away they positioned themselves. The cemetery was visibly cleared out beforehand, so there’s no sense of how Madonna would indulge or restrain grief amid the general public as any other person would consider. She’s wired for sound, so there can be no stolen moment whatsoever. And while she’s hardly writhing around on the ground as some accounts would paint it, she’s still pantomiming and performing. That’s not a knock, just a natural expectation of a 32-year-old who lost her mother at the age of 5. Under those circumstances, any mourning will feel as ephemeral and incomplete as memories of the departed. It feels like Madonna’s communion with an abstraction, an angelic afterglow you’re supposed to feel about a parent lost so early that you never knew them warts and all.
Then there’s the kerfuffle in Canada, where cops threaten to arrest Madonna if she simulates masturbation during a sultry, slowed-down version of “Like a Virgin.” Her security detail takes bets on how much she’ll just go at it harder, and you can feel an almost demonic takeover as she thrusts and thrashes against the pillows. The cops then say they saw nothing wrong with her performance and leave without incident. Although they’re doing it to appease a complaining higher-up and cover their bases, they know, like Madonna, how to work a game of appearances.
Truth or Dare is a bit more malformed during the “family” moments that concern Madonna’s dancers, stylists and backup singers. Among them, Oliver Crumes gets the most screen time, with scenes centered around a reconnection with his estranged father, tabloid rumors that he’s Madonna’s lover and his flubbed attempts to correctly pronounce Sandra Bernhard’s name. One segment juxtaposes Crumes’s heterosexual discomfort with his gay colleagues’ flamboyance against those colleagues in a moment of silent reflection during a Pride parade. The underlying idea is that sexual persecution unfairly persists everywhere. But the rest of the film never individualizes any of these gay dancers’ personal lives or backgrounds as it does Crumes, largely reducing them to clichéd cattiness in response to his tabloid presence.
Retrospective reads on Truth or Dare have heralded it as a hallmark moment for the LGBTQ community, even drawing comparisons to Paris is Burning. And while its no-big-deal approach to two men kissing or discussing sexuality is commendable, the film also more or less sweeps even those moments up into Madonna’s window dressing. Perhaps the praise response speaks more to how starved that community was at the time for any sort of on-screen representation than the pedigree of what Keshishian and company put forth.
There’s also a shockingly casual, and brief, conversation with a female stylist who was assuredly drugged and robbed but perhaps sexually assaulted. At times, “Places! Places! Prayer’s over!” seems to be as much the rallying cry for the movie to move on as it was for a Blond Ambition show to go on. At least a backup singer’s joke about how Madonna might alter lyrics to “Like a Virgin” when touring at 65 lands with more liveliness 30 years down the road.
The connotations of free-spirited family also carry a contemporary clang considering that Crumes, along with dancers Kevin Stea and Gabriel Trupin, filed suit against Madonna and the filmmakers in 1992 — claiming that the non-concert scenes made them the subject of contempt and ridicule by revealing intimate facts about their personal lives. The much lauded same-sex kiss is apparently a scene Trupin sought to remove, to which Madonna allegedly said: “Get over it.” The lawsuit was dismissed after a 1994 out-of-court settlement, prompting Keshishian to later say: “That’s why celebrities grow more and more weary of getting close to anybody.”
On one hand, Keshishian has a point. Even the eminently danceable “Vogue” boasts this lyric: “You try everything you can to escape the pain of life that you know.” On the other hand, the message of Truth or Dare, whether in its immediate moment or three decades on, is not “Don’t cry for me, rich Madonna.” Keeping her promise and her distance is part and parcel of why she remains one of the planet’s most famous people.
Although somewhat dated in their visual language, the performance sequences emphasize how much humanity Madonna had to limit to her songwriting — a small subsection of songcraft that feels simultaneously specific and universal. It’s rarefied air that few pop stars breathe. Truth or Dare shows just how much Madonna worked her ass off to cultivate pop-culture candor, not only in how she actually felt but how she thought she should feel to push buttons of political provocation. Keshishian says he turned down countless offers from other pop singers to give them the Truth or Dare treatment. A smart move, as Madonna has embraced this notion of authenticity through deceptive means more than any other pop star. Certainly no one has quite mastered the big-star, little-girl dichotomy so deeply, although Swift (in her earliest years) came close. Even at Madonna’s lowest moments in Truth or Dare, joy is not far behind — the pride of hard work on the Blond Ambition tour embodying itself as nothing less than the time of her life.
As a title, Truth or Dare of course represents the classic giggly game concerning the choice between explicit revelations or embarrassing actions, in which Madonna indulges round after bawdy round with her back-up crew. But the movie illustrates that “and” was the conjunction Madonna more often conjured for this phrase. The idea of realizing where the artifice becomes armor feels ancient today given everything Truth or Dare facilitated about subsequent chronicles of the mega-famous or, in the case of MTV’s The Real World, everyday folks. But back then, Truth or Dare represented something as bold as its subject itself. It asked not that you empathize with how hard it was to be Madonna, but simply experience how hard it was to not be Madonna … and then rip up the very notion of hardship altogether by just dancing along.