Tommy (Tim Allen) is fresh out of prison and ready for a second chance in life. Enter his loving sister Viki (Sigourney Weaver), her cynical husband Ed (J.K. Simmons) and their family. Tommy moves in with them, and when it comes to explaining to Grandma Tommy's whereabouts for the last three years, the truth-challenged Viki has the answer: "He's been in France!"
With Grandma now speaking only French to Tommy and sporting a beret, Tommy is determined to flee Viki's house and complete the two missions closest to his heart: One, to revive his late father's business and two, to re-connect with his old flame Christy (Julie Bowen). Tragically Christy died in an accident. Or so says sister Viki.
Reporting to his by-the-book probation officer Angela (Jeanne Tripplehorn) Tommy lands a temporary job in a popular fast-food chain, Pirate Burger, where not only is he forced to dress like up like something resembling Captain Hook's younger brother, but he catches a fleeting glimpse of a beautiful departing customer who looks exactly like Christy!
"Pirate" Tommy chases the woman down to discover that, indeed, it is Christy, very much alive - and engaged to be married. But that doesn't stop her from throwing herself into Tommy's arms, until their blissful reunion is interrupted by Christy's current fiancee, Frank an electronic store magnate.
Viki strikes again! But she only lied to her brother about Christy's demise to protect him from the news of Christy's nuptials. But who can protect him from his old "friend" Gray (Ray Liotta) whose video piracy operation is the reason Tommy went to jail in the first place. Gray is back on the move and trying to lure Tommy into a new scheme, and Gray isn't somebody who takes no for an answer. And while Tommy would like nothing more than to come clean to probation officer Angela, the last thing he wants to do is raise her suspicions - especially since he might be falling in love with her.
With time running out and Gray's get rich scheme advancing forward, Tommy finds himself caught between Viki who will use anything from her vast repertoire of exaggerations to save her brother, and Angela the woman he loves who also happens to enforce the law. Add to this the rest of Tommy's adoring family that is as supportive of him as they are blind to the facts and Tommy will discover that the only way to win is to be true to what's inside you, especially when it's Crazy on the Outside.