Before his commercial breakthrough with Boogie Nights (1997), writer/director Paul Thomas Anderson made this low-key drama.
Sydney (Philip Baker Hall) is a poker-faced professional gambler with a soft heart for a hard luck story. He plays guardian angel to unlucky John (John C. Reilly) and a hooker, Clementine (Gwyneth Paltrow), whom he grows to love like a family. When John and Clementine’s honeymoon night leads to a disastrous hostage situation, Sydney takes care of it, as usual. But when slick casino pro Jimmy (Samuel L. Jackson) threatens to reveal a secret from Sydney’s past that could destroy his relationship with the newlyweds, Sydney decides to hedge his bets and leaves nothing to chance.