Bobby (Jon Favreau) is a down-trodden amateur boxer who spends nights escorting his stripper girlfriend Jessica (Famke Janssen). Unfortunately, whenever a client gets fresh with the girl, Bobby gets rough with the client, so his boss decides to let Bobby into his criminal enterprises. Bobby is dispatched to New York City to participate in a drop. As usual, Bobby takes the opportunity to help out his deadbeat best friend Rickie (Vince Vaughn). The pair's tumultuous relationship and clueless attempts to be New York gangsters carry most of the plot.
This film provides examples of:
- All Bikers are Hells Angels: Ruiz has a number of black outlaw bikers under his command.
- Blatant Lies: When a gangster recognizes Rickie's Weapon for Intimidation as a starter pistol, Rickie lamely protests, "I make my gun look this way... because I am smart."
- Deconstruction: Of the type of fast-talking, ladies man character Vaughn played in Swingers. As Vaughn's character fails to charm a stewardess and just annoys her, director Favreau says in the DVD commentary "When Fonz hits the jukebox in this movie, the record player doesn't come on. Fonz gets thrown out."
- Dumbass Has a Point: Rickie is so overbearing that it's easy for Bobby to ignore a lot of what he says, but Bobby actually bows to some of his logic, for better or worse. Most notably, Rickie predicts the need for a firearm during the deal.
- Heterosexual Life-Partners: Bobby and Rickie have been best friends since at least high school. At the end they have clearly formed a nuclear family with Bobby's adopted daughter.
- Hookers and Blow: Janssen's character plays a part in this trope after the protagonist's return to L.A.
- The Irish Mob: The pair's job involves meeting an Irish gangster, from Ireland, and doing a deal. A rival faction of Irish gangsters also become involved. Bobby and Rickie argue whether the rival gang are the legendary Westies.
- Like an Old Married Couple: The epilogue shows Rickie and Bobby acting just like this — as an added bonus, they're raising a child together.
- The Mafia: It's implied that Falk's character is in the Mafia, though it's never stated outright.
- The Millstone: Rickie. He plays the part so well that it makes the film teeter between hilariously painful and too hard to watch.
- Non-Indicative Name: The Welshman is not Welsh.
- Pet the Dog: Rickie is obnoxious, but he's not a bad guy. We learn that Bobby sticks with him because Rickie chose to be expelled from high school rather than rat him out. In the end, Rickie treats Bobby's daughter with kindness and helps raise her.
- Production Throwback: The limo's license plate reads "DBLDN11," a reference to the blackjack scene in Swingers.
- Scary Black Man: Ruiz, played by Sean "Puff Daddy Combs.
- Suck E. Cheese's: The ends with a birthday party at an unnamed Suck E. Cheese's restaurant. Vince Vaughn criticizes a costumed employee for arriving only after the children have all left for the arcade, then offers him a bribe to go away.
- Vitriolic Best Buds: A great portion of the running time and comedy is the two main character arguing and coming to blows about every single little detail of their adventure.
- Weapon for Intimidation: Rickie pulls out a gun when threatened during a deal, but the other gangsters recognize it as a starter pistol.