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Dir. John Waters (1990)
This film is so quotable. In the first five minutes: "look left, look right, that's right, then walk! Good teenagers!" John Waters applies his skewed outsider sensibility to the square 1950s teen-flick in this funny quasi-musical, and it's a total gas. Starring a fresh-off-21 Jump Street teen idol version of Johnny Depp as the leader of the bad boy crew, the "Drapes," Cry-Baby follows his forbidden love with a fresh-faced "Square" played by Amy Locane. Waters' knack for weird casting makes the satire even funnier: there's Ricki Lake, Iggy Pop, and Traci Lords in small roles.
After the success of turning Waters' earlier film Hairspray into a Broadway musical, Cry-Baby the Musical had a short stint on Broadway (unfortunately) in 2008, and it closed quickly. Cry-Baby the movie, however, is still very, very fun.
Watch the film now for free on Hulu: