His first success came on radio in 1948 as high school student Walter Denton co-starring with Eve Arden and Gale Gordon in the series Our Miss Brooks.

In 1985, he won the Primetime Emmy Award for Outstanding Lead Actor in a Limited or Anthology Series or Movie for his portrayal of the title role in The Rape of Richard Beck (1985).

[5][2] After his Army service, Crenna attended the University of Southern California (USC), where he earned a Bachelor of Arts in English literature, and he was a member of Kappa Sigma fraternity.

[8] Credited as Dick Crenna, he directed eight episodes of The Andy Griffith Show during its 1963-1964 season, including "Opie the Birdman," "The Sermon for Today," and the Gomer Pyle-instigated "Citizen's Arrest."

In 1966, Crenna played beside Steve McQueen as an ill-fated captain of an American gunboat in 1920s China in The Sand Pebbles.

[8] During the 1970s, Crenna continued acting in Western dramas such as The Deserter, Catlow,[10] The Man Called Noon,[11] and Breakheart Pass.

In 1976, Crenna returned to weekly network television in the sitcom All's Fair, a political satire co-starring Bernadette Peters.

The 1978 miniseries Centennial, based on James A. Michener's historical novel of the same name saw Crenna in the role of deranged religious fanatic Colonel Frank Skimmerhorn, who ordered the 1864 massacre of Colorado American Indians.

[15][16] Crenna starred as NYPD lieutenant of detectives Frank Janek in a series of seven popular made-for-television films, beginning in 1988 and ending in 1994.