Bobby (JON FAVREAU) is an ordinary guy trying to get by in life. An aspiring, low-level boxer, he spends his days working on construction sites with his deadbeat best friend, Ricky (VINCE VAUGHN), and then nights as a bodyguard and driver for his stripper girlfriend, Jessica (FAMKE JANSSEN). Ever the opportunist, Ricky tries to persuade Bobby to ask for a higher-level job working for mob boss, Max (PETER FALK), and his persistence eventually pays off.
Accepting a high-stakes delivery job that flies them first-class to New York, the two immediately differ in their response to completing the job at hand, of which they know few details. Bobby simply wants to make the delivery and return home to Jessica and her young daughter, Chloe (MAKENZIE VEGA).
Ricky, on the other hand, suddenly thrives in his new, upscale lifestyle, and his insolent and cocksure behavior soon puts the two at risk. That's particularly true when their limo driver, Jimmy (VINCENT PASTORE), takes them to meet Manhattan mobster Ruiz (SEAN COMBS) and his right-hand man,
Horrace (FAIZON LOVE).
From that point on, as they attempt to complete their job - which includes meeting Tom the Welshman (DAVID O'HARA) who's yet another link in the criminal chain -the two find themselves in way over their heads and facing progressive amounts of risk and danger.