The big problem with this film is that any respectable gangster would have shot Ricky (Vince Vaughn) in the face the first time he made a stupid remark or screwed up a deal.
Unbelievably, Max (Peter Falk) puts up with Ricky even after Ricky sells one of his vans. Name any gangster: What would Don Corleone do to some guy who took his property and sold it, then attempted to convince him that it got stolen? The guy would wake up one day with his arms and legs in another state being used as pig feed.
For whatever reason, Max feels some affinity for Bobby (Jon Favreau) who is best friends with Ricky. Neither of them can do much right. Bobby goes ballistic when his stripper girlfriend, Jessica (Famke Janssen) gets a bit of a crotch hug from a customer. Consequently, Max sends them off to New York to do a job for Ruiz (Sean Combs), though it's not clear whether they're there to do a job or finally be offed.
It's one thing to portray a friendship as a tolerance of idiosyncrasies; it's quite another to turn those characteristics into such repetitive theater that it's like sitting next to an epileptic during a two-hour seizure. You feel bad for the epileptic, but after five minutes you start hoping somebody will come by and toss the guy out the exit door. Christ, you can have a seizure just as well outside next to a dumpster -- I'm watching a film! That's what I hoped somebody would do to Vince Vaughn throughout the entire movie, but it never happened.
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