Jerry Welbach (Brad Pitt) works for Arnold Margolese (Gene Hackman), an imprisoned mob boss. He wants to quit, but he keeps botching jobs and being told he has to do just one more. Bernie Nayman (Bob Balaban), second in command, orders him to go to Mexico to retrieve an antique pistol. When Jerry's girlfriend Sam (Julia Roberts) hears that he's not going to give up his dangerous job, she decides their relationship is over and heads off to Las Vegas where she intends to start a new life as a croupier.
In two parallel stories we follow their fates. Gore Verbinski directs this romantic comedy, which is also a road movie. The clever screenplay by J. H. Wyman constantly keeps the filmgoer off balance by dashing expectations and delivering one surprise after another.
Jerry turns out to be an amazingly incompetent fellow who gets himself in all kinds of trouble in Mexico. The pistol, he learns, has a curse attached to it and that certainly plays itself out as he struggles to get it and then keep it. A rattletrap car, a stray bullet, a mangy dog with a deflated football toy, a thief who gets shot in the foot — all of these contribute to Jerry's woes.
Meanwhile in Las Vegas, Sam is kidnapped by Leroy (James Gandolfini), a hit man who is not what he seems. It turns out that he has trouble in relationships and becomes Sam's intimate confidant. They share notes on the difficulties of staying in love when the other person is so uncooperative. Leroy, who has taken Sam as a hostage in order to insure Jerry returns with the pistol, eventually is forced to go to Mexico with her.
James Gandolfini steals the movie with his nuanced, funny, tender, and philosophical portrait of a sensitive hit man. The sidebar treats are the cross-cultural barbs between the Mexicans and the Americans and several versions of the fabled gun's history as a vehicle of sacrificial love.