09 – Rounders (1998)
Released at the time of the big poker boom, Rounders was met with mixed reviews upon release, but is today regarded as something of a cult film. Its coincidence with the online poker boom helped popularize a number of big poker sites in the industry. Damon plays Mike, a law student and talented poker player who agrees to help fellow gambler and friend Worm (Edward Norton) to make the $15000 needed to pay off his outstanding debts. With the deadline looming the pair hit as many of New York’s high-stake games as they can, with more than a few setbacks. The highlight of the film is undoubtedly the climactic game of heads-up Texas Hold’em between Mike and Teddy KGB, (John Malkovich) a repugnant Russian mobster.