Simon Oakland (August 28, 1915 – August 29, 1983) was an American actor of stage, screen, and television.^[1]

During his career, Oakland performed primarily on television, appearing in over 130 series and made-for-television movies between 1951 and 1983. 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).

Oakland was born in Brooklyn, New York,^[2] the eldest of the three sons of immigrant Jewish parents, Jacob Weiss and Ethel Oaklander, born in Romania and the Russian Empire respectively.^[3][4] His father was a plasterer and builder.^[5] While he later claimed in media interviews to have been born in 1922^[5][6] (a date repeated in his New York Times obituary),^[1][7] Social Security and vital records indicate he was born Simon Weiss in 1915; his stage name was derived from his mother's maiden name, Oaklander.^{[8][9][10][Note 1]}

He began his performing career as a musician (he was a violinist,^[12] an avocation he pursued during his entire career as an actor). Oakland began his acting career in the late 1940s. 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. He was a concert violinist until the 1940s.^{[citation needed]}

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In 1955, Oakland made his film debut, albeit uncredited, as an Indiana state trooper in The Desperate Hours. He next appeared in two films released in 1958: as Mavrayek in The Brothers Karamazov and as journalist Edward Montgomery in I Want to Live! 

Oakland's notable performance in I Want to Live! led to his playing a long series of bullying and dislikable tough-guys, either as authority figures or villains or an admixture of both. He appeared in Psycho as the psychiatrist who, at the end of the film, explains Norman Bates's multiple personality disorder. He appeared in the films West Side Story, The Sand Pebbles, and Bullitt.

He made two guest appearances on CBS's Perry Mason, both times as the murder victim. He appeared in the syndicated crime drama, Decoy, starring Beverly Garland. Oakland appeared once on the CBS Western Dundee and the Culhane and once on the series Sheriff of Cochise. He was also a regular, in a comedic supporting role, as General Thomas Moore, on NBC's Baa Baa Black Sheep, starring Robert Conrad. He appeared in two episodes of the original The Twilight Zone TV series and in The Outer Limits as the alien birdman in "Second Chance". In 1974 and 1975, he was a series regular on Kolchak: The Night Stalker, playing newspaper editor Tony Vincenzo. (He had previously played the same character in two made-for-television movies.

During the 1970s, Oakland appeared in multiple episodes of The Rockford Files, three times as blustery private detective Vern St. Cloud, a nemesis/ antagonist for Jim Rockford.

Oakland was married to Lois Lorraine Porta.^[6][13] The couple had one daughter, Barbara.^[1]

This section does not cite any sources. (December 2021)

Oakland continued working up to the year of his death. 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.