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.