Double Trouble (1967): Super-producer Irvin Winkler likes to recount an anecdote in which he, while employed on this late-period Elvis vehicle, met with longtime Presley director Norman Taurog. Not only was Taurog 68 years old, he was also legally blind in one eye, with the other one going fast. (It stopped working two years later.) So that explains Speedway.
Skidoo (1968): Before a 58-year-old Michelangelo Antonioni filmed a pair of pretty, vacant hippies in Zabriskie Point, Otto Preminger, then 62, milked the counterculture craze with this near-career-ending acid comedy. The difference? His film was less about kids than about old-timers--among them Jackie Gleason, Groucho Marx and most of the villains from the Batman TV show--trying to get down with the kids. Far more unsightly and trainwrecky than you can imagine, even before Carol Channing's striptease.
The Devil, Probably (1977): Punk legend Richard Hell once called this film about a young man flirting with but abandoning everything from nihilism to religion "the most punk film ever made." Which it likely is, though it's worth noting that at the time he made it, the great Robert Bresson (Pickpocket) was 76 years old.
Clueless (1995): Remember: Films about youth are rarely made by them. John Hughes was two decades older than his heroes, and Amy Heckerling was 41 when she inundated the world with catchphrases like "As if." You think teenagers come up with the things teenagers say?
Wassup Rockers (2005): Sure, it was creepy and pervy when Larry Clark filmed the lithe young costars of Kids when he was 42. But a 52-year-old filming even younger skateboarders, even if they were in less compromising positions? Yeesh.
Paranoid Park (2007): When once asked to name his 10 favorite films, Gus Van Sant reserved spots one through five for Clarks' Kids. But when he finally, at 55, made his own teen skateboarder pic, it was respectful without being condescending--in short, nothing like Clark. Good.
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