- 2018 Anne Hamburger
- 2017 Darko Tresnjak
- 2015 Betty Buckley
- 2014 Long Wharf Theatre, New Haven, Connecticut
- 2013 Viola Davis
- 2012 Dan Butler
- 2011 Jason Robert Brown
- 2010 Andrei Serban
- 2009 Lawrence O'Keefe
- 2009 Nell Benjamin
- 2008 Andrea McArdle
- 2007 Ernest Thompson
- 2006 Stephen Schwartz
- 2005 Betsy Palmer
- 2004 Don Holder
- 2003 Paula Vogel
- 2002 Julie Harris
- 2001 Jon Kimbell
- 2000 Maria Irene Fornes
- 1999 John Lee Beatty
- 1998 Peter Falk
- 1997 Wendy Kesselman
- 1996 Robin Wagner
- 1995 Rita Moreno
- 1994 Carol Channing
- 1993 Olympia Dukakis
- 1992 Tererence McNally
- 1991 Eric Bentley
- 1990 Paul Benedict
- 1989 Jose Ferrer
- 1988 Mark Lamos
- 1987 A. R. Gurney, Jr.
- 1986 James Kirkwood
- 1985 Robert Brustein
- 1984 Tom Jones and Harvey Schmidt
- 1983 Lloyd Richards
- 1982 Ellen Stewart
- 1981 Stephen Sondheim
- 1980 Uta Hagen
- 1979 Kitty Carlisle Hart
- 1978 Harold Clurman
- 1977 Cheryl Crawford
- 1976 Adrian Hall
- 1975 Eva LeGalliene
- 1974 Elliot Norton
- 1973 Lillian Hellman
- 1972 John Houseman
- 1971 The Open Theatre
- 1970 Harold Prince
- 1969 Arthur Miller
- 1968 David Merrick
- 1967 David Hays
- 1966 William Gibson
- 1965 Morris Carnovsky
- 1964 Lincoln Center Repertory Theater
- 1963 Joseph Papp
- 1962 Lawrence Langer
- 1961 Howard Lindsay and Russell Crouse
- 1960 Moss Hart
- 1959 Rogers and Hammerstein
- 1958 Joshua Logan
- 1957 Jo Mielziner