Knockaround Guys (2001)

Synopsis
A big score goes wrong in a big way for a bunch of aspiring gangsters in this crime comedy. Matty Demaret (Barry Pepper) is the son of a mid-level Brooklyn mob boss, Benny "Chains" Demaret (Dennis Hopper). When Matty was 12 years old, Benny and Uncle Teddy (John Malkovich) decided to see if Matty had what it took to be in the mob; they gave the boy a gun and ordered him to shoot a longtime enemy of the family. Matty lacked the nerve to do it, and ever since, Benny has been convinced his son is a coward. As an adult, Matty is stuck between a rock and a hard place; he'd like to work as a sports agent, but his family's criminal ties make that all but impossible, and his dad won't give him a chance in the family's operations. Uncle Teddy decides to give Matty a chance to make good by asking him to pick up a payment of $500,000 in Spokane, WA. Matty puts together a crew of three friends, all sons of mob guys, to help him out: muscle bound Taylor (Vin Diesel), ladies' man Chris (Andrew Davoli), and cocaine-addled would-be pilot Johnny (Seth Green). Getting the money goes just fine, but during a refueling stop in Montana, Johnny has to hide the money to keep it from being discovered. It's then promptly stolen by a pair of burnouts. When Matty and his crew discover the money is missing, they head back to Montana, but before long, they find out that the sheriff (Tom Noonan) is onto them, and that he has his own plans for the cash; they also learn that Uncle Teddy has some plans he didn't tell them about. Knockaround Guys marked the directorial debut for the screenwriting team of Brian Koppelman and David Levien. ~ Mark Deming, All Movie Guide