Penn's first great masterpiece is also one of his darkest works, a portrait of small town America as a festering backwater stagnant with avarice, envy and racism. Marlon Brando is magnificent as the weary sheriff appointed by a small town's corrupt patriarch and reluctantly assigned to capture a misunderstood fugitive, played by Robert Redford. As night descends, debauched house parties boil over into a frenzied carnival of raw violence that tears apart the flimsy façade of cracker barrel hospitality erected by the town elders. With an impressive line-up that includes Angie Dickinson, Jane Fonda, James Fox, Bruce Cabot and Miriam Hopkins, The Chase boasts an ensemble cast that draws from both Old and New Hollywood.

In 1953, Penn directed two live television dramas from scripts by Horton Foote, The Death of the Old Man and The Tears of My Sister. The broadcasts mark the beginning of Penn's work for live television, which would culminate in The Miracle Worker and launch Penn's film career, as well as the beginning of a partnership with Foote that would be renewed with The Chase (based on Foote's play and subsequent novel). The Tears of My Sister is narrated by a young girl, whose voice we hear but whom we do not see, played by Kim Stanley, as she watches her older sister struggle with the pressure to marry a man she does not love.