Tommy (Tim Allen) has just come out after spending three years in jail and is living with his sister Vicky (Sigourney Weaver) and her family. Tommy wants to get back with his old girlfriend Christy (Julie Bowen) but Vicky tells him that she is dead. He later finds that Christy is alive but engaged and that Vicky had lied to keep the knowledge of engagement from him. Further, his ex-partner in crime Gray (Ray Liotta) is back. Tommy also starts falling in love with his probation officer Angela (Jeanne Tripplehorn) and thus does not want to tell her anything about Gray. Vicky wants to keep him safe and will do anything for it.