Comedy written by and starring Luke Wilson. When conman Wendell Baker's (Wilson) latest hustle backfires, he ends up behind bars. The optimistic Wendell makes the most of his time in jail by reading several books about hotel management as he plans his next scam. After his release, Wendell gets a job at a Retirement Hotel where he meets Boyd (Seymour Cassel), Skip (Harry Dean Stanton) and Nasher (Kris Kristofferson). However, Wendell is distraught to discover that while he was in jail, his long-term girlfriend, Doreen (Eva Mendes), left him for another man - bad-tempered grocer, Dave (Will Ferrell). With the help of his new friends, Wendell makes a spirited attempt to win Doreen back, while simultaneously leading a rebellion against the hotel's evil head nurse, Neil King (Owen Wilson), and his right-hand man, McTeague (Eddie Griffin).