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Movies like Broke Even (2000)

Dot, Lem and Curry, three hapless working-class chums living in the Bronx, have a penchant for gambling. While riding a rare winning streak, they decide to shift their focus from the New York Yankees to a controversial investment practice known as "viatical settlements" -- purchasing the life insurance policies of terminally ill patients as commodities. Convinced that betting on someone to die has Karmic ramifications, Dot distances himself from his buddies and instead pursues a romance with the free-spirited Leslie. As Dot gambles on something even more complex than viaticals, a subtly vibrant relationship between him and Leslie gracefully unfolds.