1985-1986 32nd Drama Desk Awards
| Outstanding Actor - Musical | Cleavant Derricks (Big Deal) | |
| Howard McGillin (The Mystery of Edwin Drood) | ||
 |
George Rose (The Mystery of Edwin Drood) | |
| Outstanding Actor - Play | Jeff Daniels (Lemon Sky) | |
|
Ed Harris (Precious Sons) | |
| Kevin Kline (Hamlet) | ||
| Jack Lemmon (Long Day's Journey Into Night) | ||
| John Mahoney (House of Blue Leaves) | ||
| Roshan Seth (Map of the World) | ||
| Outstanding Actress - Musical | Debbie Allen (Sweet Charity) | |
| Patti Cohenour (The Mystery of Edwin Drood) | ||
| Terri Klausner (Goblin Market) | ||
| Cleo Laine (The Mystery of Edwin Drood) | ||
| Ann Morrison (Goblin Market) | ||
|
Bernadette Peters (Song and Dance) | |
| Outstanding Actress - Play | Joan Allen (The Marriage of Bette and Boo) | |
| Stockard Channing (House of Blue Leaves) | ||
| Judith Ivey (Precious Sons) | ||
| Swoosie Kurtz (House of Blue Leaves) | ||
| Kathryn Pogson (Aunt Dan and Lemon) | ||
|
Lily Tomlin (The Search for Signs of Intelligent Life in the Universe) | |
| Outstanding Book of a Musical | Stanley Donen (Singin' in the Rain) | |
|
Rupert Holmes (The Mystery of Edwin Drood) | |
| Marta Kauffman, Seth Friedman, David Crane (Personals) | ||
| Warren Leight (Mayor) | ||
| Peter Martins (Song and Dance) | ||
| Outstanding Choreography | Bob Fosse (Big Deal) | |
| Gene Kelly, Twyla Tharp (Singin' in the Rain) | ||
| Outstanding Costume Design | Joseph Aulisi (Precious Sons) | |
|
Lindsay Davis (The Mystery of Edwin Drood) | |
| Jane Greenwood (The Iceman Cometh) | ||
| Outstanding Director - Musical | Andre Ernotte (Goblin Market) | |
| Bob Fosse (Big Deal / Sweet Charity) | ||
| Paul Lazarus (Personals) | ||
|
Wilford Leach (The Mystery of Edwin Drood) | |
| Outstanding Director - Play | Liviu Ciulei (Hamlet) | |
| Jonathan Miller (Long Day's Journey Into Night) | ||
| Mary Robinson (Lemon Sky) | ||
| Gary Sinise (Orphans) | ||
| John Tillinger (Loot / It's Only a Play) | ||
|
Jerry Zaks (House of Blue Leaves / The Marriage of Bette and Boo) | |
| Outstanding Featured Actor - Musical | Jason Alexander (Personals) | |
| Gregg Burge (Song and Dance) | ||
| Joe Grifasi (The Mystery of Edwin Drood) | ||
|
Michael Rupert (Sweet Charity) | |
| Outstanding Featured Actor - Play | James Gammon (A Lie of the Mind) | |
|
Joseph Maher (Loot) | |
| Donald Moffat (The Iceman Cometh) | ||
| Anthony Rapp (Precious Sons) | ||
| Outstanding Featured Actress - Musical | Elizabeth Berridge (Cruise Control / Wrestlers) | |
| Faye Grant (Singin' in the Rain) | ||
| Bebe Neuwirth (Sweet Charity) | ||
|
Jana Schneider (The Mystery of Edwin Drood) | |
| Outstanding Featured Actress - Play | Desiree Coleman (Big Deal) | |
|
Joanna Gleason (It's Only a Play / Social Security) | |
| Kathryn Grody (The Marriage of Bette and Boo) | ||
| Kathryn McAteer (Mayor) | ||
| Anne Wedgeworth (A Lie of the Mind) | ||
| Zoe Wanamaker (Loot) | ||
| Outstanding Lighting Design | Pat Collins (Execution of Justice) | |
|
Paul Gallo (The Mystery of Edwin Drood) | |
| Phil Monat (Goblin Market) | ||
| Kevin Rigdon (Prairie du Chien and the Shaw / Mamet Double Bill) | ||
| Outstanding Music | |
Rupert Holmes (The Mystery of Edwin Drood) |
| Polly Pen (Goblin Market) | ||
| Charles Strouse (Mayor) | ||
| Andrew Lloyd Webber (Song and Dance) | ||
| Outstanding Musical | Big Deal | |
| Goblin Market | ||
|
The Mystery of Edwin Drood | |
| Personals | ||
| Outstanding New Play | Aunt Dan and Lemon (Wallace Shawn) | |
| Benefactors (Michael Frayn) | ||
| Execution of Justice (Emily Mann) | ||
|
A Lie of the Mind (Sam Shepard) | |
| The Marriage of Bette and Boo (Christopher Durang) | ||
| Precious Sons (George Furth) | ||
| Outstanding One Person Show | |
Eric Bogosian (Drinking in America) |
| James McElwaine (Goblin Market) | ||
| Elisabeth Welch (Time to Start Living) | ||
| Outstanding Orchestration | Ralph Burns (Sweet Charity) | |
|
Rupert Holmes (The Mystery of Edwin Drood) | |
| Outstanding Revival of a Play | The House of Blue Leaves | |
| The Iceman Cometh | ||
|
Lemon Sky | |
| Long Day's Journey Into Night | ||
| Loot | ||
| Outstanding Set Design | William Barclay (Goblin Market) | |
| Ming Cho Lee (Execution of Justice) | ||
| Thomas Lynch (Little Footsteps) | ||
| Bob Shaw (The Mystery of Edwin Drood / Hamlet) | ||
|
Tony Walton (The House of Blue Leaves / Social Security) | |
| Outstanding Sound Design for a Play | Tom Morse (Execution of Justice) | |
|
Otts Munderloh (The Search of Signs of Intelligent Life in the Universe) | |
| Red Clay Ramblers (A Lie of the Mind) | ||
| Outstanding Special Effects | Showtech Inc.(Singin' in the Rain ) | |
| Special Awards | |
Thomas Z. Shepard |
|
The New Amsterdam Theatre Company | |
|
The Joyce Theatre | |
|
Hume Cronyn | |
|
Jessica Tandy | |
|
Agnes de Mille | |
|
Donald Pippin | |
| Unique Theatrical Experience | |
The Search for Signs of Intelligent Life in the Universe |
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