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Long Strange Trip, or The Writer, the Naked Girl, and the Guy with a Hole in His Head (1999)
Not Jerry Garcia, more like Dennis Hopper
Despite the title, this is not a Grateful Dead bio pic. It starts out as a '90s styled "independent vision" like "The Daytripers" or "Next Stop Wonderland" that looks like it was shot by Raoul Coutard on a tiny budget. Debra Pralle even looks a bit like Hope Davis but then it gets a lot weirder, going into its own territory that's kind of like a crazy admixture of '80s road flicks like "Ruben & Ed" and darker, more bizarre '70s stuff like "Two Lane Blacktop" or "The End of The Road," and Dennis Hopper's madness in movies like the Canadian nightmare "Out of The Blue" or the proto-Vanilla Ice "White Star." Huh? Yep! Sometimes it's hard to tell whether you should laugh or run, esp. when they finally get to the deserted militia camp, where it almost plays like "Ninth Configuration" rehersals.
The female lead (Jennifer France) is hot, the main guy (Peter Wick, who also directed) has an odd, kinda Charles Grodin dead pan acting style that's totally straight up and there's piles of weird cameos and enough general weirdness, that if a few more people saw it, it might become a minor cult film like "The Next Big Thing or "American Movie." Cool!