1991-1992 38th Drama Desk Awards
| Outstanding Actor - Musical | Peter Gallagher (Guys and Dolls) | |
| Gregory Hines (Jelly's Last Jam) | ||
| Nathan Lane (Guys and Dolls) | ||
| Spiro Malas (The Most Happy Fella) | ||
| Outstanding Actor - Play | F. Murray Abraham (A Life in the Theatre) | |
| Brian Bedford (Two Shakespearean Actors) | ||
| Dennis Boutsikaris (Sight Unseen) | ||
| James McDaniel (Before It Hits Home) | ||
| Brian Murray (A Small Family Business) | ||
| Outstanding Actress - Musical | Sophie Hayden (The Most Happy Fella) | |
| Donna Murphy (Song of Singapore) | ||
| Faith Prince (Guys and Dolls) | ||
| Outstanding Actress - Play | Jane Alexander (The Visit) | |
| Glenn Close (Death and the Maiden) | ||
| Laura Esterman (Marvin's Room) | ||
| Deborah Hedwall (Sight Unseen) | ||
| Outstanding Book of a Musical | George C. Wolfe (Jelly's Last Jam) | |
| Outstanding Choreography | Christopher Chadman (Guys and Dolls) | |
| Hope Clarke, Gregory Hines, Ted L. Levy (Jelly's Last Jam) | ||
| Susan Stroman (Crazy for You) | ||
| Outstanding Costume Design | Gabriel Berry (Tis Pity She's a Whore) | |
| Toni-Leslie James (Jelly's Last Jam) | ||
| William Ivey Long (Crazy for You) | ||
| William Ivey Long (Guys and Dolls) | ||
| Outstanding Director - Musical | Gerald Gutierrez (The Most Happy Fella) | |
| Mike Ockrent (Crazy for You) | ||
| George C. Wolfe (Jelly's Last Jam) | ||
| Jerry Zaks (Guys and Dolls) | ||
| Outstanding Director - Play | Joanne Akalaitis (Tis Pity She's a Whore) | |
| Michael Bloom (Sight Unseen) | ||
| David Chambers (Search and Destroy) | ||
| Patrick Mason (Dancing at Lughnasa) | ||
| Mark Wing-Davey (Mad Forest) | ||
| Outstanding Director - Play | Dancing at Lughnasa | |
| From the Mississippi Delta | ||
| Mad Forest | ||
| Outstanding Featured Actor - Musical | Bruce Adler (Guys and Dolls) | |
| Walter Bobbie (Crazy for You) | ||
| Savion Glover (Jelly's Last Jam) | ||
| Scott Waara (The Most Happy Fella) | ||
| Outstanding Featured Actor - Play | Giancarlo Esposito (Distant Fires) | |
| Larry Fishburne (Two Trains Running) | ||
| Zeljko Ivanek (Two Shakespearean Actors) | ||
| Mark Rosenthal (Marvin's Room) | ||
| Outstanding Featured Actress - Musical | Liz Larsen (The Most Happy Fella) | |
| Michele Pawk (Crazy for You) | ||
| Tonya Pinkins (Jelly's Last Jam) | ||
| Barbara Walsh (Falsettos) | ||
| Outstanding Featured Actress - Play | Christine Baranski (Lips Together, Teeth Apart) | |
| Lisa Emery (Marvin's Room) | ||
| Harriet Harris (Bella, Belle of Byelorussia) | ||
| Laura Linney (Sight Unseen) | ||
| Nancy Marchand (The End of the Day) | ||
| Outstanding Lighting Design | Christopher Akerlind (Mad Forest) | |
| Trevor Dawson (Dancing at Lughnasa) | ||
| Jules Fisher (Jelly's Last Jam) | ||
| Paul Gallo (Guys and Dolls) | ||
| Mimi Jordan Sherin (Tis Pity She's a Whore) | ||
| Outstanding Lyrics | Susan Birkenhead (Jelly's Last Jam) | |
| Michael Garin, Paula Lockheart, Erik Frandsen, Robert Hipkins (Song of Singapore) | ||
| Outstanding Music | Erik Frandsen, Michael Garin, Paul Lockheart, Robert Hipkins (Song of Singapore) | |
| Outstanding Music in a Play | Jan A.P. Kaczmarek (Tis Pity She's a Whore) | |
| Richard Peaslee (Akin) | ||
| Outstanding Musical | Crazy for You | |
| Jelly's Last Jam | ||
| Outstanding New Play | Dancing at Lughnasa (Brian Friel) | |
| Lips Together, Teeth Apart (Terrence McNally) | ||
| Mad Forest (Caryl Churchill) | ||
| Marvin's Room (Scott McPherson) | ||
| Sight Unseen (Donald Margulies) | ||
| A Small Family Business (Alan Ayckbourne) | ||
| Outstanding One Person Show | Stan Freeman (At Wit's End)Josh Kornbluth (Red Diaper Baby) | |
| Kevin Kling (Home and Away) | ||
| Patrick Stewart (A Christmas Carol) | ||
| Outstanding Orchestration | William D. Brohn (Crazy for You) | |
| John Carlini (Song of Singapore) | ||
| Luther Henderson (Jelly's Last Jam) | ||
| Outstanding Revival of a Musical | Falsettos | |
| Guys and Dolls | ||
| The Most Happy Fella (Broadway) | ||
| The Most Happy Fella ( N.Y. City Opera) | ||
| Outstanding Set Design | John Conklin (Tis Pity She's a Whore) | |
| Joe Vanek (Dancing at Lughnasa) | ||
| Robin Wagner (Crazy for You) | ||
| Tony Walton (Guys and Dolls) | ||
| James Youmans (Bella, Belle of Byelorussia) | ||
| Outstanding Sound Design - Play | Paul Arditti (Four Baboons Adoring the Sun) | |
| Mark Bennett, Jim Van Bergen (Lypsinka! A Day in the Life) | ||
| Stewart Werner (Lips Together, Teeth Apart) | ||
| Special Awards | Andre Bishop | |
| The Irish Repertory Theatre | ||
| Broadway Cares/Equity Fights AIDS | ||
| Suzanne Ishee | ||
| Unique Theatrical Experience | Blue Man Group in Tubes | |
| Pageant | ||
| Lypsinka! A Day in the Life |
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