Col. Frank Slade has a very special plan for the weekend. It involves travel, women, good food, fine wine, the tango, chauffeured limousines and a loaded forty-five. And he's bringing Charlie along for the ride.
Charlie Simms (Chris O'Donnell) is a student at a private preparatory school who comes from a poor family. To earn the money for his flight home to Gresham, Oregon for Christmas, Charlie takes a job over Thanksgiving looking after retired U.S. Army officer Lieutenant Colonel Frank Slade (Al Pacino), a cantankerous middle-aged man who lives with his niece and her family.