He has three siblings: Jonathan Douglas,[1] a retired professor of statistics and actuarial science at The University of Iowa, Daniel Walter Cryer,[2] author of a biography of theologian Forrest Church as well as a former Newsday critic and Pulitzer Prize finalist, and Mary Kathleen (Kathy), a teacher.

He became deeply involved in music, playing trombone in the orchestra, and Ray North's dance band, and singing in The Lost Chords (a quartet modeled on The Four Freshmen), the University Choir, the Collegians, Opera Workshop, the SDX Revue, and the Monon Revue.

Leading roles off Broadway were in The Fantasticks, The Streets of New York, Mademoiselle Colombe, 'Now is the Time for All Good Men' and The Making of Americans.

[3] On the road he played opposite Anna Maria Alberghetti in West Side Story, Giorgio Tozzi and Ricardo Montalbán in The King and I, Dyan Cannon in I Do!

I Do!, Debby Boone in The Sound of Music, and Judy Kaye in Sweeney Todd: The Demon Barber of Fleet Street.

[7][8] In 1966, Cryer was one of the founders of the American Conservatory Theater in Pittsburgh, which shortly thereafter moved to San Francisco.

[9] With his second wife, the dancer and actress Britt Swanson,[10] he is the father of four children: Rachel, Daniel, Carolyn,[11] and Bill.