Hill delighted reviewers (though the box office was meager) with "The World of Henry Orient" (1964), starring Peter Sellers, and took his first abortive stab at shepherding a big-budget project, the critical and commercial failure "Hawaii" (1966). His fortunes changed for the better with his first and only movie musical the Roaring Twenties spoof "Thoroughly Modern Millie" (1967), which made a good deal of money and set the stage for his greatest triumphs, two fluid, lightly handled vehicles for the superstar team of Paul Newman and Robert Redford: "Butch Cassidy and the Sundance Kid" (1969) and "The Sting" (1973). The latter earned eight Oscars including Best Picture and one for Hill as Best Director. In between, "Slaughterhouse Five" (1972), adapted from the Kurt Vonnegut novel, won a special jury prize at Cannes but proved uncommercial. Hill also teamed with Redford on "The Great Waldo Pepper" (1975), his hymn to the great aerial stuntman of his boyhood, and with Newman for the hockey burlesque "Slap Shot" (1977).
With "A Little Romance" (1979), Hill returned to the territory he had explored so sensitively in "The World of Henry Orient", that of adolescent infatuation. Most critics enjoyed the engaging tale of 13-year-olds in love, the gorgeous European locations, the fine acting (including Laurence Olivier's wily old con man) and direction that never wallowed in sentiment, and the public seemed to agree, disregarding the naysayers who dismissed it as a gimmicky product of commercialism. Hill next shocked Hollywood by leaving to teach a class in drama at his alma mater Yale but came back to make "The World According to Garp" (1982), adapted by Steve Tesich from the John Irving novel. Although it couldn't capture Irving's literary imagination, "Garp" offered excellent performances, particularly by Glenn Close (in her film debut) and John Lithgow as a transsexual; both earned Oscar nominations for their work. Hill rounded out his filmmaking career with the unsuccessful thriller "The Little Drummer Girl" (1984) and the mild comedy "Funny Farm" (1988) before returning to academia.