Benton was encouraged to move into directing in 1972 by Stanley Jaffe, then president of Paramount, and has, despite a number of misfires, made a number of fine films, several of which have enjoyed considerable critical and popular acclaim. His very first film was a minor gem. "Bad Company" (1972) got lost amid the many other revisionist Westerns of the period but boasted grim humor and compelling detail in its story of drifters in the Old West. Benton received an Oscar nomination for his offbeat script for the amusing and clever detective story "The Late Show" (1977), which he also directed, and enjoyed the popular reception of his work on the screenplays for "What's Up Doc?" (1972, written with Buck Henry and Newman) and "Superman" (1978, written with Mario Puzo, Newman and Newman's wife Leslie). He then hit the jackpot with "Kramer vs. Kramer" (1979), which completed a trend away from macho male stars to sensitive, family-oriented men. A straight forward, sober account of a divorce custody battle told from the father's point of view, the film won Oscars for both Dustin Hoffman and Meryl Streep, and Benton himself copped two awards for his direction and screenplay. The film itself also took Best Picture.

Not a prolific filmmaker, Benton did not come out with another film until 1982's disappointing mystery muddle, "Still of the Night" (1982), which starred Streep. He had rather more luck with his original semi-autobiographical Academy Award-winning screenplay for "Places in the Heart" (1984), and he guided Sally Field to an Oscar for her portrayal of a resolute farmwoman in Depression-era Texas. The comedy thriller "Nadine" (1987) passed by without garnering much notice, however, and Benton suffered a much larger setback with his expensive but unpopular production of "Billy Bathgate" (1991). Returning to the Depression to tell the story of a young boy who rises up in the mob scene with the help of gangster Dutch Schultz, the film boasted a handsome production and fine period detail, but viewers didn't seem to warm sufficiently to either the story or the performances.

Benton did score a modest success with and earned a seventh Oscar nomination for his script for "Nobody's Fool" (1994). An adaptation of Robert Russo's novel about an irresponsible sixtyish man drawn into a family crisis, the film featured a strong central performance by Paul Newman and wonderful character turns from Jessica Tandy, Pruitt Taylor Vince and Bruce Willis. Benton and Newman reteamed for "Twilight" (1998), a contemporary--and too conventional, considering the talent involved--detective thriller co-starring Gene Hackman, Susan Sarandon and a pre-fame Reese Witherspoon. After a lengthy hiatus, Benton recruited a powerhouse (if slightly miscast) ensemble of actors--Anthony Hopkins, Nicole Kidman, Ed Harris and Gary Sinise--when he helmed the film adaptation of novelist Phillip Roth's "The Human Stain" (2003), a complex tale that the director crafted with a clear and confident feel for the emotional themes involved though the picture didn't quite capture the raw passion and anger of Roth's source material.