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Watch the Tunes: Madonna: Truth or Dare

On May 6, 2016

There is an absurdly vast selection of music movies and documentaries available on Netflix, Hulu, HBO Go, and on and on and on. But it’s hard to tell which ones are actually worth your 100 minutes. Watch the Tunes will help you pick what music doc is worth your Netflix and Chill time every weekend. This week’s edition covers Madonna: Truth Or Dare, which is streaming over at Netflix.

I’m honestly surprised that this was my first time sitting down and watching Madonna: Truth Or Dare. Both this film and her coffee table book of “scandalous” photos came out around the same time as I was heading into puberty and I, like most boys around that age, was obsessed with seeing naked women as often as possible. I know it makes me sound old and all, but a legitimate film (distributed by Miramax!) that was notable for a brief glimpse of a nude Madonna seems like a thing I would’ve found a way to watch somehow or other. But enough about the more debased aspects of the film, which are actually pretty tame by today's standards, since there’s so much more in there that’s worth digging into.

Almost in a dead heat with the music itself, Madonna is maybe best known for all of the artistic modes that she’s taken on over her career. Capturing her 1990 Blond Ambition World Tour, Truth Or Dare finds her kind of straddling two of those phases and catches some of the growing pains associated with that position. She’s touring in support of her fourth album, Like A Prayer, but she’s pulling double duty promoting her acting and singing work in the film Dick Tracy which was supposed to reignite her acting career, which had stalled out after a couple of bombs. Sean Penn had come and gone from her life at this point, taking all the tumult (and some withdrawn domestic abuse charges) that he brought with him. By the time the cameras start rolling, Madonna is dating Warren Beatty, who makes a few profoundly awkward appearances in the film and seems to totally misunderstand everything that it means to be the boyfriend of The Material Girl. It’s no surprise that their romance would wrap up not long after the period of time covered here.

As a documentary, Truth Or Dare is pretty damn odd. It’s such a fascinatingly imbalanced film, with moments shoehorned in that are designed to humanize Madonna for the audience, like her trip to the cemetery where her mother was buried and sequences where her dysfunctional brother simultaneously rides her coattails and then lets her down. But then you get these extremely petty moments like when she mocks Kevin Costner (rockin’ one hell of a mullet I might add) behind his back, which is just so stupidly juvenile and she caught some flack for leaving it in. All of the performance footage is shot in color, but everything else is in black and white which isn’t exactly the most inventive way to go about keeping the backstage from spilling onto the main stage, but it works well enough here. You definitely get the sense that Madonna’s life was just non stop over the top showmanship, and based on previous Watch The Tunes entry Who the F**k Is Arthur Fogel, tickets to homegirl’s shows are STILL worth every penny.

One of the most interesting lasting effects of Truth Or Dare is the almost omnipresence of Madonna’s crew of backup dancers. In 1991 when the film came out, the voice of gay people was rarely heard as loudly as it was presented here. Truth Or Dare never makes any overt political statements past following one of the dancers to a New York pride parade and capturing a pointed moment of silence one assumes is for victims of AIDS or any other of the legitimately terrible things that could happen to you for being out in America. Madonna is very vocal in the self-appointed motherly position she holds these dancers, herding them like cats and scolding them when they fight with each other. In other aspects of the film though, Madonna is comparatively less compassionate. When it’s revealed that one of the makeup artists in her entourage has been drugged and raped and Madonna (herself a sexual assault survivor) seems to shrug it off.

For all of its tonal inconsistencies, Truth or Dare never feels sluggish and still feels pretty vital since it captures Madonna at the arguable peak of her pop cultural power. The performances that are shown, sometimes with technical glitch warts and all, are crazy and theatrical, but they’re somehow upstaged by all the absorbing drama going on behind the scenes, however ginned up some of it might be. She’s the perfect diva, the party girl with the heart of gold who can charm her way out of any mess she gets herself into. Truth or Dare more than holds up as both a document of that time in Madonna’s multi-faceted career, but it also somehow captures her essence and shows she maybe hasn’t changed that much in the twenty five years since it came out. I’m actually kinda glad I waited as long as I did to take this in since the meat of it would’ve gone right over my head, and now it seems more like a living bit of road map point the way towards everything that would happen later for Madonna.


Profile Picture of Chris Lay
Chris Lay

Chris Lay is a freelance writer, archivist, and record store clerk living in Madison, WI. The very first CD he bought for himself was the Dumb & Dumber soundtrack when he was twelve and things only got better from there.

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