His most notable big-screen roles were in Psycho (1960), West Side Story (1961), The Sand Pebbles (1966), Bullitt (1968), The Hunting Party (1971), and Chato's Land (1972).

He enjoyed a series of Broadway hits, including Light Up the Sky, The Shrike, and Inherit the Wind, and theater was one of his lasting passions.

[citation needed] In 1955, Oakland made his film debut, albeit uncredited, as an Indiana state trooper in The Desperate Hours.

During the 1970s, Oakland appeared in multiple episodes of The Rockford Files, three times as blustery private detective Vern St.

His last credited acting appearance was in the episode "Living and Presumed Dead" on the CBS television series Tucker's Witch.

That episode aired three months before Oakland's death from colon cancer in Cathedral City, California, on August 29, 1983, the day after his 68th birthday.