Born in New York City, Cypher graduated from Erasmus Hall High School (1949) and Brooklyn College (1953).
Cypher later received a master's degree in marriage and family counseling from the University of Vermont.
Cypher made his television debut as the Prince in the original 1957 production of Rodgers and Hammerstein's Cinderella opposite Julie Andrews in the title role. He is particularly remembered as Chief of Police Fletcher Daniels in Hill Street Blues, a role he played throughout the run of the series (1981–87). He played Commanding General Marcus Craig on Major Dad, alongside Gerald McRaney and Beverly Archer, and appeared as Howard Millhouse in the short-lived television series Probe. He played Dr. Alex Keith on As the World Turns (1977–79) and Dr. Arthur Donnelly on Santa Barbara (1988–89).

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