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Fresh out of prison and eager to start a new life, ambitious ex-con Tommy (Tim Allen) plots to revive the family business and rekindle the romance with his ex-flame, only to discover that life as a free man can be even tougher than life on the inside. In order to get back on his feet, Tommy moves in with his extended family, including his sister, Viki (Sigourney Weaver), a compulsive liar, and her husband, Ed (J.K. Simmons), a weatherworn cynic. Thanks to Viki, Tommy's grandmother thinks he's been in France the last few years. Now, as Tommy scrambles to get his life back together, his no-nonsense probation officer, Angela (Jeanne Tripplehorn), tracks his every move. Informed by his sister that his former girlfriend Christy (Julie Bowen) perished in a freak accident, Tommy goes to work flipping patties at Pirate Burger. Then, one day, Christy walks into the restaurant and it's like they were never apart -- aside from the fact that she's now engaged to marry Frank (Kelsey Grammer). Meanwhile, as Tommy's criminally inclined pal Gray (Ray Liotta) attempts to lure him back into a life of petty thievery, the confused ex-con begins to feel like he's falling for his probation officer.