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 lifetime 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).
Cypher had an active career on the stage in both musicals and plays. He made his Broadway debut as Wister LaSalle in the original 1959 production of Harvey Breit's The Disenchanted. He returned to Broadway in 1962 to replace Patrick O'Neal as the Reverend T. Lawrence Shannon in the original production of Tennessee Williams's The Night of the Iguana. He portrayed the role of Dr. Carrasco in the original 1965 cast of Man of La Mancha, later taking over the role of Don Quixote.
Cypher made his first film appearance as the villain Frank Tanner in the 1971 Western Valdez Is Coming opposite Burt Lancaster and Susan Clark. He took on the role of the heroic Man-at-Arms in the 1987 Masters of the Universe movie. Cypher has since appeared periodically in films up through the late 1990s in mostly featured character parts.
In 1967, he performed the role of Bert Jefferson in the original musical Sherry! by James Lipton and Laurence Rosenthal. His other Broadway credits include The Great White Hope, 1776, Coco, and Big: the musical. In 1993, he sued a theater and a performance company in Pittsburgh for $20,000 over a fall he suffered during a dress rehearsal on July 20, 1992. Cypher broke his leg in two places and damaged cartilage and ligaments when he fell down a darkened stairway at the Benedum Center, where he played Fagin in the Civic Light Opera production of Oliver! The incident left Cypher playing the character while seated in a wheelchair. In a 2013 interview, Cypher revealed he still walked with a cane.
In a 2014 interview, he stated that poverty was the secret to his 47-year-long career.
