Matty Demaret (BARRY PEPPER) is a young man haunted by both his past and family name. When he was younger, his uncle, Teddy Deserve (JOHN MALKOVICH), couldn't persuade him to shoot the man who framed his mobster father, Benny Chains (DENNIS HOPPER), and thus he was never considered for any sort of position in the Brooklyn-based crime family.
Being the son of Benny, however, has caused no one to hire him for fear of being tangled up with the mob. Reduced to being his father's errand boy, Matty wants something more and eventually convinces Benny to allow him to transport half a million dollars across the country.
Unfortunately, Matty enlists the aid of Johnny Marbles (SETH GREEN), his nervous and former coke-head friend, to pick up the bag in Spokane and fly it back to New York. When he spots Sheriff Decker (TOM NOONAN) and Deputy Gray (SHAWN DOYLE) during a refueling stop in Wibaux, Montana, however, he panics and stashes the bag with others tagged for another flight.
While distracted by the local law officers who eye him suspiciously, Marbles doesn't realize that some local airport personnel have found the bag and taken it for themselves. When Marbles reports this to Matty, he, Marble's cousin, Chris Scarpa (ANDREW DAVOLI), and their tough guy friend, Taylor (VIN DIESEL), set off for the small town.
Once there, they attempt to recover the money, but one complication after another soon turns what should have been an easy job into an increasingly dicey and dangerous situation. With Teddy and his goons on the way, Matty and the others race to resolve the situation before time runs out.