Leonard is a three-time Tony Award nominee (1993, 2001 and 2003), winning in 2001 (Best Actor – Featured Play) for his role as A. E. Housman in Tom Stoppard's The Invention of Love.
Leonard je tri puta nominiran za nagradu Tony (1993., 2001. i 2003.), a te 2001. je i dobio nagradu (Najbolji glumac u predstavi) za svoju ulogu A.E. Housmanu u predstavi Izum ljubavi Toma Stopparda.