Bobby (Vince Vaughn) and Ricky (Jon Favreau) are probably the worst boxers ever to enter a ring. Their so-called boxing career is cut short when Ricky is conscripted by mob boss, Max (Peter Falk, aka Columbo) into a money laundering job. Bobby's arrogance, thick-headedness and plain stupidity cause trouble from beginning to end. Ricky's devotion to his friend's well being is a testament to his character as well as Bobby's saving grace.Vaughn's character is maddening. And very funny. He is told not to get drunk while on the job so he drinks constantly. He is given 1500 dollars to last for an indefinite period of time and he blows it all in one night. If it wasn't for Ricky, Bobby wouldn't even have his job sweeping up at mob affiliated construction sites. It turns out Bobby does have a sweetness to his character but you have to wait for it. Bobby comes off as loveable because he's played by Vaughn. He can't do anything wrong when he's on screen. As long as he's smiling, the world around him melts away. Bobby likes to tell jokes about fags but because Vaughn is such a fence-sitter the jokes come off as ironic more than homophobic. At the end, Bobby and Ricky end up living together and acting like an old married couple. It's very cute.
Puff Daddy, in a surprise role, plays a gang leader. He plays the part well. It's like he's really acting and not just portraying an exaggeration of his already exaggeration public image. Famke Janssen plays Ricky's girlfriend, Jessica, a stripper who proves herself to not be worth the attention that Ricky lavishes on her.Seeing the streets of Manhattan made me a little homesick. For a gangster flick, its short on action, short on testosterone and short on evil gangsters. It's really a sweet story about a guy who is trying to make everyone else's life better in the only way that he has available to him. Jon Favreau is the charming hero who plays the straight guy to Vaughns fuck up friend who you end up liking in spite of yourself.