->''"Did you just let Screech into the fucking club? I'm waiting in line, and you just let Screech into the fucking club."''
->-- '''Rickie'''

Bobby (Creator/JonFavreau) is a down-trodden amateur boxer who spends nights escorting his stripper girlfriend Jessica (Creator/FamkeJanssen). Unfortunately, whenever a client gets fresh with the girl, Bobby gets rough with the client, so [[TheDon his boss]] decides to let Bobby into his criminal enterprises. Bobby is dispatched to New York City to participate in [[MacGuffin a drop]]. As usual, Bobby takes the opportunity to help out his deadbeat best friend Rickie (Creator/VinceVaughn). The pair's [[VitriolicBestBuds tumultuous relationship]] and [[FishOutOfWater clueless attempts]] to be New York gangsters carry most of the plot.

This 2001 film was Favreau's directorial debut, and was largely marketed as a SpiritualSuccessor to his and Vaughn's previous work on ''Film/{{Swingers}}''.
!!This film provides examples of:
* AllBikersAreHellsAngels: Ruiz has a number of black outlaw bikers under his command.
* {{Deconstruction}}: Of the type of fast-talking, ladies man character Vaughn played in ''Film/{{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."
* DumbassHasAPoint: 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.
* HeterosexualLifePartners: 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.
* HookersAndBlow: Janssen's character plays a part in this trope after the protagonist's return to L.A.
* TheIrishMob: 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.
* LikeAnOldMarriedCouple: The epilogue shows Rickie and Bobby acting just like this -- as an added bonus, they're raising a child together.
* TheMafia: It's implied that Falk's character is in the Mafia, though it's never stated outright.
* TheMillstone: Rickie. He plays the part so well that it makes the film teeter between hilariously painful and too hard to watch.
* NonIndicativeName: The Welshman is not Welsh.
* PetTheDog: 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.
* ProductionThrowback: The limo's license plate reads "[=DBLDN11=]," a reference to the blackjack scene in ''Swingers''.
* ScaryBlackMan: Ruiz, played by Sean "Puff Daddy Combs.
* SuckECheeses: 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.
* VitriolicBestBuds: 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.