Trixie Zurbo (EMILY WATSON) is a well-intentioned security guard who's been assigned to undercover work at a lakefront casino watching for pickpockets and the like. Known for butchering well-known sayings through her constant, but unconscious use of malapropisms, Trixie instantly befriends several of the regulars including barfly Ruby Pearli (BRITTANY MURPHY) and washed-up lounge act and impersonator Kirk Stans (NATHAN LANE).
She also meets Dex Lang (DERMOT MULRONEY), a self-proclaimed ladies man who immediately tries to put the moves on her. After repeated attempts at doing so, Dex finally convinces Trixie to come along for an afternoon of fun on a yacht owned by his boss, Red Rafferty (WILL PATTON), a corrupt and mean spirited land developer.
Unbeknownst to Dex, Red has arrived with his two henchmen, Vince (MARK ACHESON) and
Sid Deflore (VINCENT GALE), after arranging an impromptu get-together on his yacht for State Senator Drummond Avery (NICK NOLTE) and Dawn Sloane (LESLIE ANN WARREN), a strung-out, lounge singer who never attained success.
Red isn't happy about Trixie's presence, but she makes an impression on both Avery and Sloane before being escorted off the yacht. Upset at what occurred, Dex quits, but before he and Trixie consummate an amorous encounter, the Deflore brothers show up, asking about the whereabouts of Dawn and a missing videotape, before beating up Dex.
A closet sleuth, Trixie then sets out to find Dawn and the videotape, and figure out what's on it that's caused such behavior. As she does - and continues to drop one malapropism after another -- Trixie discovers a web of intrigue, danger and political corruption in her first real detective case.