Broke Even (2000)

This film focuses on a trio of down-and-out gambling slackers. Dot (Kevin Corrigan), Lem (Mick Cunningham), and Curry (Michael Lowry) spend much of their time sucking down beer and making back bets on Yankees games, until they stumble upon the investment opportunity of a lifetime -- or so they think. As their luck seems to turn, Dot tries to go straight and pursue a free-spirited young woman named Leslie (Elizabeth Berridge). Yet, when the three's investment proves to be not what it seems, Dot is forced to choose between his buddies and the girl he loves.