Luke Wilson stars as Wendell Baker - a good-hearted conman whose latest scam lands him in jail and alienates him from everyone he loves, including his longtime girlfriend Doreen (Eva Mendes). Eternally optimistic, Wendell makes the most of his time behind bars and vows to turn his life around. Upon release, he gets a job at the Shady Grove Retirement Hotel, where he befriends residents Boyd (Seymour Cassel), Skip (Harry Dean Stanton) and Nasher (Kris Kristofferson).
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Wendell's new friends help him to win back his girlfriend, while he leads them in a spirited rebellion against the hotel's evil head nurse, Neil King (Owen Wilson) and his right-hand man, McTeague (Eddie griffin).