She Knows How to Work It: Madonna: Truth or Dare Turns 25

With the 25th anniversary of Madonna's underappreciated documentary, we take a look at what it means to be a "calculating" celebrity woman—then and now.

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She Knows How to Work It: <i>Madonna: Truth or Dare</i> Turns 25

Twenty-five years ago this month, Madonna’s self-celebrating documentary Madonna: Truth or Dare was released. The film, which joins Madonna on her blockbuster 1990 Blonde Ambition tour, promised a “backstage” look at the world-famous pop star “as she really is,” but with its staged “confessions” and cheekily pretentious, black-and-white art-house style (likely an homage to D.A. Pennebaker’s famous Bob Dylan study Dont Look Back), Madonna: Truth or Dare challenged expectations.

It did not introduce audiences to a more down-to-earth star. It did not present a likable Madonna. Instead, Truth or Dare provided a portrait of Madonna the constant performer, at times abrasive and demanding, in control of every aspect of her career. Criticized upon its release for being “contrived” and “manipulated” by its subject—for its failure to reveal what audiences conceived to be a hidden “real Madonna”—the film is often gleefully phony. It is fascinating to watch for precisely the reason it was criticized—it is Madonna’s story told completely on Madonna’s terms, and challenges the idea of what is acceptably “real” when it comes to female celebrities.

What is “real,” and why is it something we expect of our pop icons?
Particularly when applied to female celebrities, it’s usually shorthand for down-to-earth and humble, describing an average person thrust into stardom, not one who instigates it. Kelly Clarkson is “real” because she was just a small-time Texas girl who won American Idol, while Lana del Rey is “fake” because she changed her image and gave herself a stage name in order to further her musical career. Personal crises also serve to make stars seem “real” by this definition—just look at the popularity of Jennifer Aniston and Jennifer Garner, two stars who suffered through public divorces and displayed emotional vulnerability in the press.

Being “real” usually translates to being “likable,” something against which Madonna has spent her career fighting. Yet, she still faces pressure to prove she is “real,” as do her successors in pop stardom, women like Beyoncé and Taylor Swift. What makes Madonna: Truth or Dare so compelling 25 years later is the way it subtly mocks this definition of “real,” extending a defiant middle finger into the face of “likability.”

It’s hard to remember now just how captivating a figure Madonna was in 1991, at the height of her music-bred fame, branching out into acting and keeping tabloid editors busy with her divorce from Sean Penn and subsequent romance with Warren Beatty. Known for unapologetically pushing boundaries of sexuality and exhibitionism, she was a woman constantly under a microscope. So, she decided to take that to its logical conclusion: Why not have cameras follow her around 24/7, recording her every dance rehearsal and bawdy backstage joke?

Madonna: Truth or Dare chronicles an especially grueling five-month tour at the height of Madonna’s international stardom (i.e., in her ice-blond, fake ponytail, underwear-over-clothing era). The film finds her at 32 years old, already a seasoned veteran of the music business and the pop-star life—she’s bossy, bitchy and funny, totally unafraid to show it. In Truth or Dare, we see Madonna as she sees herself, and the documentary highlights what she feels is important, not what someone else wants to reveal about her. In turn, director Alek Kesheshian takes an obviously hands-off approach, capturing a Madonna that is ultimately in charge of her image, her team and the documentary itself, bossing him around when he’s not actively deferring to her. In even the film’s final shot, Madonna hollers, “Cut it, Alek, goddamn it!”

Mixing on stage performances with backstage drama—Madonna bonding with her exuberant team of male dancers, joking with her brother Christopher, yelling at various members of the tech crew, lounging in glamorous robes and speaking directly to the camera in “confessional” portions—Madonna doesn’t hesitate to incorporate her personal life into all she does. Whether she’s dragging a recalcitrant Warren Beatty before the camera, meeting somewhat awkwardly with her father, or dishing with friend Sandra Bernhard, she rarely comes across as particularly “nice” or “likable,” preferring to be provocative above all. Madonna’s flippant attitude toward personal matters is captured in an exchange with Bernhard:

Madonna: I had those dreams when my mother died. For like a five-year period after that, that’s all I dreamed about—that people were jumping on me and strangling me. And I was constantly screaming for my father, and no sound would come out.
Bernhard: What happened when you woke up? You were crying?
Madonna: I’d be sweating and afraid and have to go sleep with my father.
Bernhard: Was that before he got remarried? How was that when you slept with him?
Madonna: Fine. I went right to sleep after he fucked me. [Laughter] I’m just kidding!

She can’t resist disrupting a moment of sincerity, upending the expectation that she recount her childhood trauma on camera. She does this throughout Truth or Dare, joking about deeply personal matters and then attempting to refocus the film’s attention on the rigors of the tour, which is clearly what she believes to be more important.

Truth or Dare’s central concern, then, is not to accurately depict Madonna’s personal relationships, but to showcase the pop star as the boss, a role that, in 1991, many did not see her inhabiting.

She was still often characterized as a provocateur with little substance, a performer whose creative output was the product of producers and hired professionals. In Truth or Dare she’s still very much the provocateur, but she’s also the prickly professional, demanding and exacting, sweating it out on stage night after night alongside a crew that obviously looks to her as their leader. Roger Ebert, who gave the film a positive review, praised its focus on the work of pop stardom, writing, “The organizing subject of the whole film is work. We learn a lot about how hard Madonna works, about her methods for working with her dancers and her backstage support team, about how brutally hard it is to do a world concert tour.” The film’s emphasis on Madonna’s intentionality is plainly stated on camera by one of her dancers: “She knows what she’s doing and she knows how to work it and that’s what’s important. That’s why she’s such a big star.”

But seeing Madonna as hardworking curator of her tour, image and brand was not what audiences had hoped for. Many critics expressed disappointment with the absence of what they considered the “real Madonna” (presumably a Madonna with her guard down, which still sounds like an oxymoron 25 years later). Most seemed to agree that the documentary’s “contrived” or “performative” nature was its major flaw. The Washington Post asked, “…where does Madonna-faux end and Madonna-real begin? Is there a real Madonna?” , while The New York Times conceded, “The image of her that emerges here, however contrived and sometimes poisonous, is in the end as seductive as she means it to be.”

The film inspired a particularly vitriolic reading by Bill Wyman of the Chicago Reader, who wrote, “Far from candid, the film is actually carefully contrived, its star so obsessively in control that you wish someone had made an actual documentary (‘The Making of Truth or Dare’) that laid bare the manipulations.” Madonna’s control of her own documentary, her presentation of herself as she wants to be seen, renders it somehow not “real,” as though we need to see someone else’s take on Madonna to get to the heart of who she is. The “real Madonna” many desired to see—a less calculating, softer, more vulnerable creature—may very well not exist, but it’s a role she’s expected to play.

In 2016, we are perhaps more open to celebrating ambition and business acumen in female celebrities, but the problem of the “c” word persists. There’s a mythic moment in a woman’s career when the scale tips from “hardworking” to calculating, typically resulting in a negative turn in press coverage. Earlier this year, in Chuck Klosterman’s revealing GQ interview with Taylor Swift—certainly a pop star/mogul in the Madonna vein—the writer gets closer than most to addressing Swift’s complicated relationship to authenticity. Noting that a source in the industry has referred to Swift as “calculating,” he writes:

She really, really hates the word calculating. She despises how it has become tethered to her iconography and believes the person I met has been the singular voice regurgitating this categorization. […] “Am I shooting from the hip?” she asks rhetorically. “Would any of this have happened if I was? In that sense, I do think about things before they happen. But here was someone taking a positive thing—the fact that I think about things and that I care about my work—and trying to make that into an insinuation about my personal life. Highly offensive. You can be accidentally successful for three or four years. Accidents happen. But careers take hard work.”

Swift is offended at the implication that because she is in control of her career she is also a cold and controlling person in all aspects of her life. This is not only the same accusation still leveled at Madonna, but at other famous women as well. In this election year, the most notable target of such judgment is Hillary Clinton, who has been characterized for years in conservative media as a power-hungry, career-obsessed harridan. For a politician, it’s an endless high-wire act to balance likeability with intelligence, vision and competence—for a female celebrity in the realm of entertainment, however, a choice is usually made, and likeability almost always wins.

Which may seem harmless—until it comes to the issue of equal pay for women. Reigning America’s Sweetheart Jennifer Lawrence stated as much last year in her widely circulated essay for Lenny entitled “Why Do I Make Less Than My Male Co-Stars?” She writes, “I would be lying if I didn’t say there was an element of wanting to be liked that influenced my decision to close the deal without a real fight. I didn’t want to seem ‘difficult’ or ‘spoiled.’” While the reaction to her letter was mainly positive, she was also harshly criticized, particularly by conservative media outlets. When condescendingly labelled her essay a “bratty display from a wealthy youngster,” Lawrence fired back: “Thank you for proving my point. Would you have called a man a brat?”

While for female celebrities, being “likeable” or “real” is still often shorthand for easygoing, modest and often emotionally vulnerable, we have arrived at a cultural moment in which we are more comfortable in seeing that hustle Madonna exhibits, in both the creative and business realms. A case in point is Beyoncé, whose work ethic and meticulous management of her career are generally viewed as assets. As Spencer Kornhaber wrote in The Atlantic in 2013, “The idea that great pop takes work should be a no-brainer. But even before the mini-scandal over her lip syncing of the national anthem at President Obama’s inauguration, stars like Beyoncé have been criticized as talentless, prepackaged—fake.” He goes on to suggest that Beyoncé’s 2013 Super Bowl performance then made its ambition, difficulty and effort plain, which served to humanize that pop cultural entity dubbed “Queen Bey” by showing that she is a person of creative talent and agency.

For Beyoncé, the work is everything, and what little we know of her personality comes through her music. She goes to great lengths to avoid personal engagement with the press, and skillfully strategizes ways to demonstrate her humanity and authenticity without the kind of open engagement key to Taylor Swift’s career. Her documentary Life is But a Dream, which promised to “strip away the veneer of stardom,” seemed calibrated to offer fans and the media just enough to keep them interested without really revealing anything. Like Truth or Dare, Life is But a Dream was criticized for providing too little insight into Beyoncé, though her misstep was the opposite of Madonna’s: Knowles-Carter focused almost entirely on the quasi-personal rather than the professional or creative. Jody Rosen of The New Yorker called it “vague, determined not to offend,” and “a torrent of banalities,” noting that “…there’s no question that Beyoncé is a terrible judge of what is interesting about Beyoncé.”

But with Lemonade, it seems like Beyoncé has finally struck that elusive balance which allows her to be perceived as both “real” and in control. Beyoncé was widely praised for this year’s Super Bowl performance of “Formation,” which plainly focused on racial issues in America. The media did not hesitate to credit Beyoncé herself with the impressive concept, mainly because it seemed personal, a controversial, risky performance of the kind not usually programmed by executives. Similarly, the visual album Lemonade reels fans in with the personal, raising questions about her famous marriage and feelings about race and identity while still maintaining her image as a strong, independent woman. She’s maybe revealing her deepest vulnerabilities through her art—maybe. She’s established such a pattern of withholding that Lemonade feels like an opening of the floodgates, a window into a star’s soul.

In reality? It’s just as controlled as any of Madonna’s confessions in Truth or Dare. Both films are examples of art that tease intimacy. Will fans ever know the “real” Madonna? Will we ever find out if Jay-Z really cheated on Beyoncé? “No” and “it’s highly unlikely,” respectively. Like Swift said, careers take hard work, and she, like her fellow superstars, has stayed on top in part because of her adeptness at both integrating and separating art, business and personal life.

Being calculating is not just unavoidable—it’s absolutely essential to career longevity. Madonna: Truth or Dare was far ahead of its time in its recognition of this fact, and its willingness to tackle these questions of authenticity and work and female-ness. Twenty-five years on, the film still feels refreshing, boldly refusing to perpetuate the image of yet another vulnerable female star tossed on the turbulent seas of fame and steadied by the hands of so many managers and handlers. In Truth or Dare, Madonna refuses to diminish herself for our affection. She doesn’t care that she’ll be called “calculating”—in fact, she’d probably take it as a compliment.