Leonard is a three-time Tony Award nominee, and won Best Featured Actor in a Play in 2001 for his role as A. E. Housman in Tom Stoppard's The Invention of Love. He had previously played the role of Valentine in the New York premiere of Stoppard's Arcadia at Lincoln Center in 1995. He was nominated for a Tony in 2003 for his portrayal of Edmund Tyrone in a well-received revival of Eugene O'Neill's Long Day's Journey Into Night; it co-starred Philip Seymour Hoffman, Brian Dennehy, and Vanessa Redgrave. Leonard has also appeared in Broadway musical productions, in 2001 replacing Craig Bierko as the lead performer in a revival of The Music Man. Leonard co-starred as Paul Verrall in the 2011 Broadway revival of Born Yesterday.
