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John (played by Steve Buscemi) is a down-on-his-luck gambler who, after many defeats at the card table, finally understands the lesson that failure has taught him: to give up gambling, find a job, and live a normal life. Thus, John earns a dead-end job at a car insurance company, where he deals with the daily mundane tasks while battling his inner demons. One day, John is assigned by his boss to assist a lie detector named Virgil (played by Romany Malco) in investigating a bizarre car accident, which may be John's only chance for a promotion. At the same time, John encounters a co-worker named Jill (played by Sarah Silverman), and their teasing gradually develops into love.
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