Perry established himself as a TV documentary producer before making an acclaimed feature directorial debut with "David and Lisa" (1962), written by his wife Eleanor. A sensitive, finely acted portrait of two mentally disturbed teenagers, the black-and-white film was shot on a minimal budget and possessed a distinctly independent tone. Perry and his wife collaborated on several more offbeat and savvy studies of social mores, notably their adaptation of the John Cheever short story, "The Swimmer" (1968; direction completed by Sydney Pollack) and "Diary of a Mad Housewife" (1970). Perry's work, always earnest if rather obvious, suffered somewhat following his divorce in 1970 but he returned to form with the spoof western, "Rancho Deluxe" (1976), scripted by novelist Thomas McGuane. He scored another popular success with the suburban satire "Compromising Positions" (1985).
Perry's work in fiction TV was infrequent but memorable. He produced and directed "A Christmas Memory" (ABC, 1966), a superior TV-movie adapted from Truman Capote's Southern childhood memoir of a holiday spent with his eccentric aunt Sookie. Still aired periodically, the telefilm has become something of a classic. Two years later, Perry returned to Capote country for "Thanksgiving Visitor" (ABC, 1968). After a long hiatus from the medium, he helmed "Dummy" (CBS, 1979), a powerful crime docudrama starring LeVar Burton as an illiterate deaf-mute accused of murder and Paul Sorvino as his deaf court-appointed attorney. Perry also directed Abby Mann's teleplay for "Skag" (NBC, 1980), a memorable TV-movie cum successful pilot starring Karl Malden as a feisty aging steel worker battling back from a stroke.
In 1990, Perry was diagnosed with inoperable prostate cancer. As part of his battle against the disease, he produced, directed and starred in "On the Bridge" (1993), a filmed journal that explored the various methods of treatments he underwent and also included interviews with cancer patients and oncologists. Perry believed that by working on the film, he had prolonged his life.