31 Years Later, ‘Madonna: Truth Or Dare’ Might Be Her Most Important Work 

Like the classic rockers a generation above her, Madonna has no interest in throwing the towel in or acting her age. While similar artists — hold up, record scratch, there are no similar artists — while other artists of her era play with their stock portfolios and finalize their retirement plans, Madonna’s vaping in clubs with Kanye and posting nude selfies on Instagram. It might not always be the best look, but you have to admire her, in the same way we admire an old boxer willing to put his hands up against a younger competitor and, let’s be real, the competition is none.  

Ironically, if anyone has a right to rest on her laurels, it’s Madonna Louise Ciccone. With each passing year, the depth of her influence seems to increase. It’s hard to imagine most of the stars of the last 25 years without her blueprint to follow, her melding of music, message and celebrity, and the way she elevated her personal life to be on par with her professional work. Nowhere is her impact more apparent than in her 1991 tour documentary Madonna: Truth or Dare, which is currently available for streaming on Pluto TV.   

Originally envisioned as a simple concert film of 1990’s Blond Ambition World Tour, director Alek Keshishian encouraged Madonna and her entourage’s  backstage shenanigans. Besides the singer, this includes her stage crew, backup singers, dancers, and visiting celebrities, including then-boyfriend Warren Beatty. Madonna narrates the movie like she’s reading from her diary, as if we’re getting to see the real Madonna, but of course any time the cameras are turned on the reality stops being real. Madonna knows this and uses it to create the image of herself she wants to present.   

The tour and film starts overseas, where Madonna works her crew like a boss fixing technical and performance glitches. When the outdoor performance is threatened by cold and rain, the troupe band performs in matching with dark bomber jackets. The crowd doesn’t seem to care. As is often the case watching Madonna live, I’m always impressed at how much better a singer she is than she’s ever given credit for. Later, Madonna admits she’s not the best singer but that’s only part of what she does. Touring behind 1989’s Like A Prayer album, she had been a superstar for over half a decade at this point but the film catches her at her zenith and the set list reflects her biggest hits.

Madonna’s inner circle includes her backup singers and dancers, the latter of which are predominantly gay men of color. Truth or Dare has been applauded for the exposure it gave Black and latino gay men, and it’s important to remember how much LGBTQ life was once relegated to the shadows. It seems almost de rigueur nowadays for pop starlets to cultivate a large gay fanbase and publicly proclaim themselves as their allies. We can thank Madonna for that, and we should. One of the film’s most emotional and celebratory moments is when she performs at an AIDS benefit dedicated to Keith Haring, the artist and a personal friend who died from the disease months earlier. 

Musing over her tour party, Madonna says she’s “unconsciously chosen people that are emotionally crippled in some way or who need mothering.” Of course, they’re also her employees and there’s zero doubt that she is the matriarch and center of attention. Her professional relationships are contrasted with more difficult relationships with her family and romantic interests. Her brother arrives at her Detroit concert fresh out of rehab and her father complains about her show being too racy. Beatty, meanwhile, blanches under the constant filming of every personal moment and voices his disapproval, highlighting his and Madonna’s 20 year age gap.  

Truth or Dare famously concludes with Madonna playing a game of truth or dare and romping in bed with her inner circle. Between deep-throating an Evian bottle and asking one of her dancers to show her his penis there are moments of emotional honesty, such as when she admits actor and ex-husband Sean Penn was the love of her life. At another point she says she’s interested in “pushing people’s buttons and being provocative.” While the scenes are played up for titillation and effect, one is reminded how she made an artist’s love life and sexual history a marketing strategy.

31 years on, Madonna: Truth Or Dare is utterly entertaining and a vital document of Madge at her peak. What’s more remarkable is how it created the modern concert documentary from the ground up, blending performance footage with backstage drama and using both to build the artist’s myth and curate its legend. Its imitators are many. Ultimately, it may be Madonna’s defining work, capturing her essence in a way that transcends the constraints of a mere pop song. She’s  always been more than just that. 

Benjamin H. Smith is a New York based writer, producer and musician. Follow him on Twitter: @BHSmithNYC.