In his return to screenwriting and debut as director, Luke Wilson plays a good-hearted conman named Wendell Baker whose latest scam lands him in jail and alienates him from his longtime girlfriend Doreen (Eva Mendes), best friend Reyes (Jacob Vargas) and even his dog, Junior.

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). Wendell's new friends advise him on how to win back his girlfriend, while he helps them battle the hotel's evil head nurse, Neil King (Owen Wilson) and right-hand man, McTeague (Eddie Griffin).