The Indian Runner (1991) Penn's directing debut spins Bruce Springsteen's song ''Highway Patrolman'' into a gritty, thoughtful domestic drama about two tormented brothers (David Morse and Viggo Mortensen) on opposite sides of the law. Penn also found a rare role for Charles Bronson (as the brothers' dad) that doesn't involve him shooting anybody.
The Crossing Guard (1995) Penn draws a typically scary and intense performance from Jack Nicholson as a man bent on exacting violent revenge on the drunk driver (Morse) who killed his daughter. Penn also manages the impressive diplomatic feat of getting real-life exes Nicholson and Anjelica Huston to work together.
Into the Wild (2007) Penn's best film yet is this dreamy biopic of Christopher McCandless (Emile Hirsch), a privileged young man who shed all his possessions, traveled across America seeking Jack Kerouac-like adventures, then headed deep into the Alaskan wilderness seeking Jack London-like adventures, where he met his fate. Penn manages both to celebrate McCandless' Thoreauvian quest to escape the bonds of civilization and to observe the pain his abandonment caused his family and others who tried to reach out to him. —Gary Susman