1950s–1970s Simon began working in films and on television after he moved to Los Angeles in 1954. In 1955, he appeared on television in episodes of
Medic and
Alfred Hitchcock Presents as well as such feature films as
Chief Crazy Horse,
Seven Angry Men, and
The Court-Martial of Billy Mitchell. In 1956 and 1957, he appeared in episodes of
State Trooper,
The Millionaire and
M Squad. In 1957, he appeared in the
Betty Hutton film
Spring Reunion, and as George Nordmann in the feature film
Edge of the City, starring
John Cassavetes and
Sidney Poitier. In 1958, Simon guest-starred as Captain Woods in "The Coward of Fort Bennett" on
General Electric Theater. In 1957 and 1958, he appeared in four episodes of the anthology series,
Playhouse 90. In 1959, he appeared on
Peter Gunn and
Adventures in Paradise. His other 1950s film credits included appearances in
The Buccaneer (1958),
Compulsion (1959),
The Last Angry Man (1959) and
Operation Petticoat (1959).
Westerns From 1956 to 1970, Simon appeared in
Broken Arrow,
Disneyland, ''
Dick Powell's Zane Grey Theatre, Laramie, Black Saddle, Law of the Plainsman, Johnny Ringo, Cheyenne, and The Dakotas, Wichita Town, The Man from Blackhawk, The Texan, Tombstone Territory, Tate, and Shotgun Slade, Stagecoach West, Bat Masterson, Lawman, Klondike, and Frontier Circus, Have Gun – Will Travel, Wagon Train, The Legend of Jesse James, The Road West, Gunsmoke ("Cheap Labor"-S2E32, "Potato Road"-S3E5, “Father’s Love” - S9E24 & "The Mission" - S12E4), Laredo, The Virginian, Bonanza, and The Guns of Will Sonnett. He portrayed Sheriff Morgan on Elfego Baca
and General Alfred Terry on Custer''. In 1962, Simon played Mackie in the episode "House of the Hunter" on CBS's
Rawhide. The same year he also portrayed Handy Strong in the feature film
The Man Who Shot Liberty Valance.
Drama Simon portrayed Dave Tobak on
Saints and Sinners. He also appeared in such programs as
Crusader,
Route 66,
Dante,
The DuPont Show with June Allyson,
Johnny Midnight,
Straightaway,
The Roaring 20s,
Sea Hunt and
State Trooper. In 1961 and 1962, he guest starred on episodes of
Ripcord,
The Dick Powell Show,
The Lloyd Bridges Show, ''
Cain's Hundred and Sam Benedict. In the controversial 1962 episode "The Benefactor" of the legal drama The Defenders, Simon played an unrepentant abortion care provider who uses his trial to argue for a change in the law. In 1966, he played Nazi officer Colonel Beckman in The Rat Patrol'' episode "The Exhibit A Raid". Simon guest-starred three times on
Perry Mason, including the role of murderer Edward Bannister in the 1958 episode, "The Case of the Desperate Daughter." Simon appeared as Harvey, friend of the main character Paul Driscoll in the 1963
The Twilight Zone episode "
No Time Like the Past". In 1965, he appeared in episodes of ''
Slattery's People, Voyage to the Bottom of the Sea, and Dr. Kildare''. During the 1960s, Simon performed as well in dramatic roles in several films, such as
The Spiral Road (1962),
Captain Newman, M.D. (1963), and
Fate Is the Hunter (1964). In 1966, he starred too as Mr. Rellik in the Highway Safety Films' production
The Third Killer. His role was that of a "Death" salesman charged with three accounts, including traffic fatalities.
Comedy Simon portrayed Frank Stephens on
Bewitched and Everett McPherson on
Nancy, He also appeared in other sitcoms, such as
Ichabod and Me, ''
McHale's Navy, Mrs. G. Goes to College, Get Smart, and The Andy Griffith Show''. He appeared in
A New Kind of Love (1963) starring
Paul Newman and
Joanne Woodward, as "Cervantes" in
The Reluctant Astronaut (1967), and as a doctor in
Private Duty Nurses (1971). He appeared in a 1970 episode of
Love, American Style, in a 1971 episode of
Nichols, starring
James Garner, and a 1973 episode of
The Partridge Family. In 1973, he made three guest appearances as General Maynard M. Mitchell on
M*A*S*H.
Later roles From 1969 to 1985, Simon appeared in
Marcus Welby, M.D.,
The Mod Squad,
The Interns,
Barnaby Jones,
The Six Million Dollar Man,
Police Woman,
Hawaii Five-O,
Cannon,
Ellery Queen,
M*A*S*H,
Columbo,
McCloud,
McMillan & Wife,
Quincy M.E.,
Eight Is Enough, and
The Feather & Father Gang. He had a recurring role as Captain Rudy Olsen on
The Streets of San Francisco and portrayed J. Jonah Jameson on
The Amazing Spider-Man (1978–1979). His last television appearance was in a 1985 episode of
Airwolf. == Personal life ==