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American Dreamer: The High Adventures of a Card-Counting Low Roller (2000)
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This docu-dramedy had me laughing until I was crying. Heartbreaking and funny at the same time, this lo-fi road movie seemed to have a real feel for the gamblers life. Traveling from one end of Nevada to the other on a wing and a prayer Mike Landry, after failing in LA as a stand-up comic hatches a hair brained idea to get rich, and make a movie at the same time. After learning a black-jack card counting system he heads out into the Nevada desert to try to make a fortune and make a movie at the same time. His strange adventures go from the hilarious to the absurd and back again. I would definitely recommend this movie - especially if you like to gamble - but even if you don't it is one wild ride!.