Taking Woodstock is in theaters Friday. Maybe it will be really good, or maybe taking a stand-up comedian and sticking him in a semi-dramatic movie about Woodstock that doesn't feature any -- any! -- musical performances is a terrible idea. Still, rock 'n' roll and Hollywood have been ugly, messy bedfellows since both things started, and Taking Woodstock would have to work pretty hard to do worse than any of these moments of crossover disaster.
You may notice an overabundance of selections from a certain ten-year span in this list. Indeed, an alternate title for this list could just be, "The '80s: What the fuck were we thinking?"
10. Vanille Ice in Cool as Ice This would be so much worse if there were any sort of reputation to ruin in the first place.
9. Mick Jagger in Freejack In the future (or the present, as the movie is set in 2009), the ozone layer is gone and there are fascists all over the place. Mick plays the witty villain with all the emotional range of a homicidal Big Bird. Actually, that makes it sound a lot better than it is. Dial this one straight to the one minute mark for some acting that's stiffer than the cover of Sticky Fingers.
8. Bruce Willis cuts The Return of Bruno Honestly, this is exactly what you should expect from Bruce Willis making music. It's nostalgic and manly and patriotic. Terrorist fightin' songs, perfect music to blow shit up to. But, you know, he's about thirty years late on rockabilly, five shades too white to be pulling off the blues, and pretty much talentless as a singer. This one's the only track he had a hand in writing on this album. Sweet shades, Bruno.
7. David Bowie in Labyrinth This clip really says it all. Open on crying baby. Pan out to show pit full of monsters with spiked helmets and one with a fu manchu. Cut to David Bowie lounging in some sort of throne. Don't show his crotch just yet. Build the anticipation. Monster shoots blow dart at rooster. Bowie stands. Keep the camera above the waist. He walks through monsters. Ass facing camera. He starts singing. It's weird, but then again this is Jim Henson and David Bowie. He tosses a monster through the air. Dance routine. Over the course of the next minute, the camera shows little glimpses. Then, at the 1:45 mark, right after he punts some creature, we get a straight-on shot. That lump you see? Just be glad the resolution isn't better. Trust me. More weird dancing. And then, right at the end, we get Bowie pitching the baby maybe ten feet in the air and letting a nearby monster catch him. Between the distinguishable penis and the abuse, this has to be in the conversation for worst children's movie ever.
6. David Hasselhoff in general. Really the whole career looks like a joke at this point, but he gets special notice here for the incredible cheesiness of his music. Exhibit A: Get In My Car, where the Hoff manages to mix the creepy side of "Baby It's Cold Outside" with American Graffiti. The green screen stuff would be a lot funnier if he weren't so cheeky about the whole thing. That's actually why he's so far down the list: He's clearly self-effacing, and it's so much less fun to laugh with someone than at him. Oh well, still a noble effort of suckitude.
5. The Apple It's supposed to be an exaggerated commentary on the music industry, with hippies on one side and big labels on the other and a ridiculously heavy-handed religious allegory in between. But bad things happen when you set a musical in a future where rock and roll has become some sort of political system, and the result is what you see below. Extra points for the shiny gold man-thong/diaper and this lyric: "It's a natural, natural, natural desire/Meet an actual, actual, actual vampire," which may be the clumsiest stanza I've ever heard.
4. Britney Spears in Crossroads It came out 2002, but this one's got all the worst parts of the '90s written all over it in big fake-pink marker. This trailer actively makes me cringe once every fifteen seconds or so, the worst moment coming in the form of a roadside tantrum thrown by stubbly man toy because Brit and her doll friends are leaking estrogen all over his convertible. I think this is supposed to be a the sort of joke where dudes in the audience look knowingly at their bros and with an expression that says, "Been there, man." Their girlfriends, meanwhile, are probably all passed out from giggling. I don't care if this was back when Britney was actually fuckable, a few seconds of lingerie does not absolve an hour and a half of cardboard bullshit.
3. Streets Of Fire The Boss wasn't thrilled with the appropriation of his title, and he ultimately forced them to drop the song from the credits, so Springsteen isn't responsible. Someone is, though, and for your consideration I present these lines from the trailer as evidence: "You are about to enter a world unlike any you've seen before, where rock 'n' roll is king, the only law is a loaded gun, where the beautiful ('Stay and see the show, it's really good') the brutal ('I want Tom Cody') and the brave all meet ('From now on it's for real') in Streets of Fire." Seriously, if Saturday Night Live just lifted this thing straight up it would be funnier than 85 percent of its current material.
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2. Graffiti Bridge The sequel to Purple Rain, this one's so high on the list because of the letdown. Look, Prince is The (androgynous) Man, and he even manages to look cool a couple times in a mostly-laughable Graffiti Bridge, but what the hell was he thinking? Just look at this traile: Kid script writing on day-glo backgrounds, exposed chest everywhere and a bunch of gangsters who make West Side Story look like The Wire.
1. Mariah Carey in Glitter A horrible movie in its own right, Glitter tops the bad decision list for its repercussions. It got Mimi dropped from her label and 20th Century Fox refused to distribute the DVD in the States. Her cleavage was nominated for a Golden Raspberry Award for Worst Screen Couple. Without the intervention of Kanye West and The Neptunes a few years later for The Emancipation of Mimi, this very well could have been a career-killer. Why all the fuss? Go straight to the 6:25 mark, where her equally incapable co-star seduces our doe-eyed heroine with a marimba solo. Honestly, I picked that scene at random -- there are wince-worthy train wrecks packed into every nook and cranny.