Stephen O'Leary (Headsman) has played a variety of roles since joining the Company in 1995, including Archibald Grosvenor in Patience, Tarara in Utopia, Limited and Ludwig in The Grand Duke, as well as Fred in A Gilbert & Sullivan Christmas Carol. He has music-directed four Off-Broadway productions with The New Punctuation Army, including the 2001 New York City premiere of A Gilbert & Sullivan Christmas Carol, which was favorably reviewed in both The New York Times and The New Yorker.

A systems programmer at New York Life, he is also music director of the New York Life Singers. He currently serves as corresponding secretary of the Company.