1995-1996 42nd Drama Desk Awards
| Honorary Awards | Repertorio Espanol | |
| Signature Theatre Company | ||
| Theatreworks USA | ||
| George C. Scott | ||
| Outstanding Actor - Musical | David Garrison (I Do! I Do!) | |
| Savion Glover (Bring in 'Da Noise, Bring in 'Da Funk) | ||
| Daniel Jenkins (Big) | ||
| Nathan Lane (A Funny Thing Happened on the Way to the Forum) | ||
| Adam Pascal (Rent) | ||
| Lou Diamond Phillips (The King and I) | ||
| Outstanding Actor - Play | Gerry Bamman (Nixon's Nixon) | |
| George Grizzard (A Delicate Balance) | ||
| Frank Langella (The Father) | ||
| Mark Nelson (Picasso at the Lapin Agile) | ||
| Rocco Sisto (Quills) | ||
| Patrick Stewart (The Tempest) | ||
| Outstanding Actress - Musical | Julie Andrews (Victor/Victoria) | |
| Terri Klausner (Bed and Sofa) | ||
| Christa Moore (Big) | ||
| Donna Murphy (The King and I) | ||
| Daphne Rubin-Vega (Rent) | ||
| Karen Ziemba (I Do! I Do!) | ||
| Outstanding Actress - Play | Catherine Byrne (Molly Sweeney) | |
| Zoe Caldwell (Master Class) | ||
| Uta Hagen (Mrs. Klein) | ||
| Lisagay Hamilton (Valley Song) | ||
| Rosemary Harris (A Delicate Balance) | ||
| Sarah Jessica Parker (Sylvia) | ||
| Outstanding Book of a Musical | Bed and Sofa (Laurnce Klavan) | |
| Big (John Weidman) | ||
| Chronicle of a Death Foretold (Jim Lewis, Graciela Daniele) | ||
| Rent (Jonathan Larson) | ||
| Outstanding Choreography | Graciela Daniele (Chronicle of a Death Foretold) | |
| Savion Glover (Bring in 'Da Noise, Bring in 'Da Funk) | ||
| Ghettoriginal Productions (Jam on the Groove) | ||
| Kathleen Marshall (Swinging on a Star) | ||
| Susan Stroman (Big) | ||
| Outstanding Costume Design | Jane Greenwood - Sylvia (The Petrified Prince) Roger Kirk - The King and I Michael Krass - Entertaining Mr. Sloane Toni-Leslie James - The Tempest Julie Taymor, Constance Hoffman - The Green Bird Angela Wendt - Rent | |
| Jess Goldstein (Love! Valour! Compassion!) | ||
| Jane Greenwood (The Heiress) | ||
| Florence Klotz (Showboat) | ||
| Stephen Brimson Lewis (Indiscretions) | ||
| William Ivey Long (A Christmas Carol) | ||
| Outstanding Director - Musical | Christopher Ashley (Das Barbecii) | |
| Michael Mayer (America Dreaming) | ||
| Trevor Nunn (Sunset Boulevard) | ||
| Harold Prince (Showboat) | ||
| Outstanding Director - Play | Declan Donnellan (As You Like It) | |
| David Esbjornson (Iphigenia and Other Daughters) | ||
| Gerald Gutierrez (The Heiress) | ||
| Emily Mann (As Having Our Say) | ||
| Joe Mantello (Love! Valour! Compassion!) | ||
| Sean Mathias (Indiscretions) | ||
| Outstanding Featured Actor - Play | Simon Coates (As You Like It) | |
| John Glover (Love! Valour! Compassion!) | ||
| Kevin Kilner (The Glass Menagerie) | ||
| Anthony LaPaglia (The Rose Tattoo) | ||
| Nathan Lane (Love! Valour! Compassion!) | ||
| Alessandro Nivola (A Month in the Country) | ||
| Outstanding Featured Actress - Play | J. Smith Cameron (The Naked Truth) | |
| Tara Fitzgerald (Hamlet) | ||
| Hallie Foote (The Horton Foote Plays) | ||
| Penny Fuller (Three Viewings) | ||
| Camryn Manheim (Missing Persons) | ||
| Sheila Tousey (Iphigenia and Other Daughters) | ||
| Outstanding Lighting Design | Beverly Emmons (The Heiress) | |
| Paul Gallo (Blade to the Heart) | ||
| Mark Henderson (Indiscretions) | ||
| Brian MacDevitt (Love! Valour! Compassion!) | ||
| Richard Pilbrow (Showboat) | ||
| Outstanding Musical | A Christmas Carol | |
| How to Succeed in Business without Really Trying | ||
| Merrily We Roll Along | ||
| Showboat | ||
| Sunset Boulevard | ||
| Outstanding One Person Show | Dan Butler (The Only Thing Worse You Could Have Told Me) | |
| Danny Hoch (Some People) | ||
| Avi Hoffman (Too Jewish?) | ||
| Lisa Kron (101 Humiliating Stories) | ||
| James Lecesne (Word of Mouth) | ||
| Outstanding Play | Arcadia (Tom Stoppard) | |
| The Cryptogram (David Mamet) | ||
| Love! Valour! Compassion! (Terrence McNally) | ||
| Missing Persons (Craig Lucas) | ||
| Raised in Captivity (Nicky Silver) | ||
| SubUrbia (Eric Bogosian) | ||
| Outstanding Revival - Reinterpetation | Cheek by Jowl (As You Like It) | |
| Indiscretions | ||
| Theatre for a New Audience (Henry VI) | ||
| Lincoln Center Theatre (The Heiress) | ||
| Roundabout Theatre Company (The Moliere Comedies) | ||
| Outstanding Set Design | Arcadia (Mark Thompson) | |
| Hapgood (Bob Crowley) | ||
| Indiscretions (Stephen Brimson Lewis) | ||
| A Month in the Country (Santo Loquasto) | ||
| The Petrified Prince (James Youmans) | ||
| Showboat (Eugene Lee) | ||
| Special Awards | The Barrow Group |
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