1989-1990 36th Drama Desk Awards
| Outstanding Actor - Musical | Mike Burstyn (The Rothschilds) | |
| David Carroll (Grand Hotel) | ||
 |
James Naughton (City of Angels) | |
| Outstanding Actor - Play | Alec Baldwin (Prelude to a Kiss) | |
| Charles S. Dutton (The Piano Lesson) | ||
|
Nathan Lane (The Lisbon Traviata) | |
| Gary Sinise (The Grapes of Wrath) | ||
| Colin Stinton (Some Americans Abroad) | ||
| Outstanding Actress - Musical | Geraldine James (The Merchant of Venice) | |
|
Mary Elizabeth Mastrantonio (Twelfth Night) | |
| S. Epatha Merkerson (The Piano Lesson) | ||
| Mary Louise Parker (Prelude to a Kiss) | ||
| Outstanding Actress - Play | Geraldine James (The Merchant of Venice) | |
| Mary Elizabeth Mastrantonio (Twelfth Night) | ||
|
S. Epatha Merkerson (The Piano Lesson) | |
| Mary Louise Parker (Prelude to a Kiss) | ||
| Outstanding Book of a Musical | City of Angels (Larry Gelbart) | |
| Outstanding Choreography | Tommy Tune (Grand Hotel) | |
| Outstanding Costume Design | Jennifer Arnold, Robert Locke (The Lady in Question) | |
| Jess Goldstien (When She Danced) | ||
| Florence Klotz (City of Angels) | ||
|
Santo Loquasto (Grand Hotel) | |
| Outstanding Director - Musical | Michael Blakemore (City of Angels) | |
| James Hammerstien (The Sound of Music) | ||
|
Tommy Tune (Grand Hotel) | |
| Outstanding Director - Play | |
Frank Galati (The Grapes of Wrath) |
| Roger Mitchell (Some Americans Abroad) | ||
| Adrian Nobel (The Art of Success) | ||
| Norman Rene (Prelude to a Kiss) | ||
| Lloyd Richards (The Piano Lesson) | ||
| Outstanding Featured Actor - Musical | Rene Auberjonois (City of Angels) | |
| Laurence Guittard (The Sound of Music) | ||
| Jonathan Hadary (Gypsy) | ||
| Michael Jeter (Grand Hotel) | ||
| Outstanding Featured Actor - Play | Rocky Carroll (The Piano Lesson) | |
|
Charles Durning (Cat on a Hot Tin Roof) | |
| Francis Guinan (The Grapes of Wrath) | ||
| Dustin Hoffman (The Merchant of Venice) | ||
| Simon Jones (Privates on Parade) | ||
| Outstanding Featured Actress - Musical | Danielle Du Clos (Aspects of Love) | |
|
Randy Graff (City of Angels) | |
| Jane Krakowski (Grand Hotel) | ||
| Crista Moore (Gypsy) | ||
| Outstanding Featured Actress - Play | Jayne Atkinson (The Art of Success) | |
| Kate Burton (Some Americans Abroad) | ||
|
Frances Conroy (The Secret Rapture) | |
| Marcia Jean Kurtz (When She Danced) | ||
| Stephanie Roth (Artist Descending a Staircase) | ||
| Outstanding Lighting Design | Andrew Bridge (Aspects of Love) | |
|
Jules Fisher (Grand Hotel) | |
| Paul Gallo (City of Angels) | ||
| Tharon Musser (Artist Descending a Staircase) | ||
| Kevin Rigdon (The Grapes of Wrath) | ||
| Outstanding Lyrics | Richard Maltby Jr. (Closer Than Ever) | |
| Robert Wright, Maury Yeston, George Forrest (Grand Hotel) | ||
|
David Zippel (City of Angels) | |
| Outstanding Music | |
Cy Coleman (City of Angels) |
| George Forrest, Maury Yeston, Robert Wright (Grand Hotel) | ||
| Astor Piazzolla (Dangerous Games) | ||
| David Shire (Closer Than Ever) | ||
| Andrew Lloyd Webber (Aspects of Love) | ||
| Outstanding Musical | Aspects of Love | |
|
City of Angels | |
| Outstanding New Play | The Lisbon Traviata (Terence McNally) | |
|
The Piano Lesson (August Wilson) | |
| Prelude to a Kiss (Craig Lucas) | ||
| The Secret Rapture (David Hare) | ||
| Outstanding One Person Show | Eric Bogosian (Sex, Drugs, Rock & Roll) | |
| Kathryn Grody (A Mon's Life) | ||
|
Robert Morse (Tru) | |
| Mandy Patinkin (Dress Casual) | ||
| Outstanding Orchestration | Rodolfo Alchourron, James Kowal (Dangerous Games) | |
|
Billy Byers (City of Angels) | |
| David Cullen, Andrew Lloyd Webber (Aspects of Love) | ||
| Peter Matz (Grand Hotel) | ||
| Outstanding Revival of a Musical | Gypsy | |
| The Sound of Music | ||
| Outstanding Set Design | Edward Gianfrancesco (The Widow's Blind Date) | |
| Kevin Rigdon (The Grapes of Wrath) | ||
|
Robin Wagner (City of Angels) | |
| Tony Walton (Grand Hotel) | ||
| Special Awards | |
The Fund for New American Plays |
|
Jules Styne | |
|
Kevin Haney (Tru) |
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