Matty Demaret (Barry Pepper) is the son of a mob leader. He was once tested to see if he would eventually join the family, but failed to shoot one of his uncles when given the opportunity when he was 12 years old. His uncle Teddy (John Malkovich) accepts it, telling him that not everyone is cut out for this kind of work.
As a young adult, Matty still wants to be accepted by his father, Benny 'Chains' Demaret (Dennis Hopper). Although treated nicely with riches and his own Cadillac, Matty is still not respected in the way that he would like to be. He has tried to move on in his life. His dream is to become a sports agent, but nobody will hire him because he carries the name of his father. It takes 11 interviews for him to realize it, but it shows that there is determination within him.
The only thing he can do is try to fit into the world that already once rejected him-the crime world. Being that 10 times less rejection then the sports' agencies, he figures that he has a shot at this. In order to prove himself, he eventually convinces his father to let him go on a mission. His job is to simply make sure a bag of money (500 grand) gets from point A to B. He puts his trust into his friend Johnny Marbles (Seth Green), who owns a small private plane, and agrees to fly the money for him across country. Johnny stops at a small airport in Montana to refuel, and becomes paranoid when he suspects that two police officers might know that he has cocaine in his possession. He releases the powder into the air, and he hides the bag in a luggage zone when he goes inside to pay, and then loses it.
Knockaround Guys is about 4 aspirating mobsters who come together in order to find the bag of money that Johnny lost. The four Brooklyn-born buddies head to a small town in Montana, where they look to start trouble in order to strike fear into whoever has the loot. They're amateurs but think they're professionals. They stick out in the dusty town wearing their shiny suits, and they think they're superior to everyone.
Taylor Reese (Vin Diesel) is the bulky guy of the group who wrecks the town's toughest person in order to get a reaction, while Matty assumes the role as the leader and does all of the talking after Taylor's victim is bleeding from the nose. Johnny is just pathetic, confused and struggling with a drug addiction that landed them there in the first place. And his cousin looks like he belongs in a business office, not in a gang.
The scene where Taylor beats up a guy in a bar deserves some recognition. Taylor was my favorite character, but not because of his muscles, but because he seemed to be the only one out of the four who knew why he was in the business. A life of crime is an allusion to the other three. After they purchase weapons, two of the four goof off at a shooting range, where it appears that they've never fired a gun before.
The small town of Wibaux is exactly the same type of small town that you see in all Hollywood movies. The sheriff is either ridiculously friendly, or more evil than corruption itself. The sheriff in this movie, played by Tom Noonan, is the evil type. He and his partner eventually get the money in their possession, and refuse to hand it over. Noonan is a tempered man with no good qualities. But he is the cop, and I'd hate to see who the criminals are in this town.
Benny's crew arrives to finish the job, and it now becomes a mob from New York versus the law of Wibaux, Montana. But don't get too excited over this match, there are very few confrontations, nothing that deserves mentioning the word 'suspense.'
Knockaround Guys is a decent movie that deals with friendship, trust and betrayal. The four kids are likable, but the real mob members arenít. Benny has no respect for his son, and it takes Matty too long to realize it.
By the end, someone has turned on someone, and that is as high as the crest on this wave ever gets. It is completely predictable, and the action is kept to a minimum. No surprises or confounding elements exist will undoubtedly make people forget this movie ever existed. Yes, it has a lot of stars in it, and that is what keeps this movie at an average level, not at the bottom of the barrel. Never mind that Knockaround Guys has been sitting on the shelf for a couple of years, the only difference would have been that back in 1999, you couldn't compare this to Road to Perdition.