1999-2000 46th Drama Desk Awards
| Outstanding New Play | Contact (Frank Gilroy) | |
 |
Copenhagen (Michael Frayn) | |
| Dinner with Friends (Donald Margulies) | ||
| Dirty Blonde (Claudia Shear) | ||
| Jitney (August Wilson) | ||
| The Tale of the Allergist's Wife (Charles Busch) | ||
| Outstanding New Musical | |
Contact |
| The Dead | ||
| Saturday Night | ||
| Swing! | ||
| The Wild Party(Manhattan Theatre Club) | ||
| Outstanding Revival - Play | A Moon for the Misbegotten (Eugene O'Neill) | |
| The Price (Arthur Miller) | ||
| The Real Thing (Tom Stoppard) | ||
| True West (Sam Shephard) | ||
| Uncle Vanya (Anton Chekhov) | ||
| Waste (Harley Granville Barker) | ||
| Outstanding Revival - Musical | Kiss Me, Kate | |
| The Music Man | ||
| Outstanding Actor - Play | Gabriel Byrne - A Moon for the Misbegotten | |
| Kevin Chamberlin - Dirty Blonde | ||
| Stephen Dillane - The Real Thing | ||
| Philip Seymour Hoffman - True West | ||
| Derek Jacobi - Uncle Vanya | ||
| Paul Sparks - Coyote on a Fence | ||
| Outstanding Actress - Play | Sinead Cusack - Our Lady of Sligo | |
| Eileen Heckart - The Waverly Gallery | ||
| Linda Lavin - The Tale of the Allergist's Wife | ||
| Claudia Shear - Dirty Blonde | ||
| Lynn Thigpen - Jar the Floor | ||
| Charlyne Woodard - In the Blood | ||
| Outstanding Actor - Musical | Hunter Foster, Little Shop of Horrors | |
| Tyrone Giordano, Big River | ||
| Hugh Jackman, The Boy From Oz | ||
| Michael McElroy, Big River | ||
| Alfred Molina, Fiddler on the Roof | ||
| Euan Morton, Taboo | ||
| Outstanding Actress - Musical | Toni Collette - The Wild Party (New York Shakespeare Festival) | |
| Heather Headley - Aida | ||
| Rebecca Luker - The Music Man | ||
| Marin Mazzie - Kiss Me, Kate | ||
| Audra McDonald - Marie Christine | ||
| Julia Murney - The Wild Party (Manhattan Theatre Club) | ||
| Outstanding Featured Actor - Play | Matthew Arkin - Dinner with Friends | |
| Roy Dotrice - A Moon for the Misbegotten | ||
| Joel Grey - Give Me Your Answer, Do! | ||
| Philip Seymour Hoffman - The Author's Voice / Imagining Brad | ||
| Brian Murray - Uncle Vanya | ||
| Harris Yulin - The Price | ||
| Outstanding Featured Actress - Play | Jillian Armenante - The Cider House Rules, Part One: Here in St. Cloud | |
| Marylouise Burke - Fuddy Meers | ||
| Seana Kofoed - An Experiment with an Air Pump | ||
| Phyllis Newman - The Moment When | ||
| Cigdem Onat - The Time of the Cuckoo | ||
| Amy Sedaris - The Country Club | ||
| Outstanding Featured Actor - Musical | Jason Antoon - Contact | |
| Christopher Fitzgerald - Saturday Night | ||
| Alistair Izobell - Kat and the Kings | ||
| Michael Mulheren - Kiss Me, Kate | ||
| Stephen Spinella - The Dead | ||
| Lee Wilkof - Kiss Me, Kate | ||
| Outstanding Featured Actress - Musical | Nancy Anderson - Jolson and Co. | |
| Sally Ann Howes - The Dead | ||
| Eartha Kitt - The Wild Party (New York Shakespeare Festival) | ||
| Alix Korey - The Wild Party (Manhattan Theatre Club) | ||
| Indina Menzel - The Wild Party (Manhattan Theatre Club) | ||
| Karen Ziemba - Contact | ||
| Outstanding Director - Play | Michael Blakemore - Copenhagen | |
| Thomas Hulce, Jane Jones - The Cider House Rules, Part One: Here in St. Cloud | ||
| James Lapine - Dirty Blonde | ||
| Michael Mayer - Uncle Vanya | ||
| Marion McClinton - Jitney | ||
| Daniel Sullivan - Dinner with Friends | ||
| Outstanding Director - Musical | Gabriel Barre - The Wild Party (Manhattan Theatre Club) | |
| Michael Blakemore - Kiss Me, Kate | ||
| Susan Stroman - Contact Susan Stroman - The Music Man | ||
| Outstanding Choreography | Contact - Susan Stroman | |
| Kat and the Kings - Jody Abrahams, Loukmaan Adams | ||
| Kiss Me, Kate - Kathleen Marshall | ||
| The Music Man - Susan Stroman | ||
| Swing! - Lynne Taylor-Corbett | ||
| The Wild Party (Manhattan Theatre Club) - Mark Dendy | ||
| Outstanding Music | The Dead - Sean Davey | |
| Saturday Night - Stephen Sondheim | ||
| The Wild Party (Manhattan Theatre Club) - Andrew Lippa | ||
| Outstanding Lyrics | The Big Bang - Boyd Graham | |
| The Bomb-itty of Errors - Jordan Allen-Dutton, Jason Catalano, Gregory Qaiyum | ||
| Saturday Night - Stephen Sondheim | ||
| The Wild Party (Manhattan Theatre Club) - Andrew Lippa | ||
| Outstanding Orchestrations | Kat and the Kings - Taliep Peterson | |
| Kiss Me, Kate - Don Sebesky | ||
| The Music Man - Doug Besterman | ||
| Saturday Night - Jonathan Tunick | ||
| Swing! - Harold Wheeler | ||
| The Wild Party ( Manhattan Theatre Club) - Michael Gibson | ||
| Outstanding Set Design - Play | Dinner with Friends - Neil Patel | |
| East is East - Derek McLane | ||
| An Empty Plate at the Cafe du Grand Boeuf - Rob Odorisio | ||
| Jitney - David Gallo | ||
| The Time of the Cuckoo - James Noone | ||
| Uncle Vanya - Tony Walton | ||
| Outstanding Set Design - Musical | Contact - Thomas Lynch | |
| Kiss Me, Kate - Robin Wagner | ||
| The Music Man - Thomas Lynch | ||
| Shockheaded Peter - Julian Crouch, Graeme Gilmour | ||
| The Wild Party (Manhattan Theatre Club) - David Gallo | ||
| Outstanding Costume Design | The Big Bang - Boyd Graham | |
| The Country Club - Jonathan Bixby, Gregory Gale | ||
| Kiss Me, Kate - Martin Pakledinaz | ||
| The Music Man - William Ivey Long | ||
| Shockheaded Peter - Kevin Pollard | ||
| The Wild Party (Manhattan Theatre Club) - Martin Pakledinaz | ||
| Outstanding Lighting Design | Contact - Peter Kaczorowski | |
| Dirty Blonde - David Lander | ||
| An Experiment with an Air Pump - Brian MacDevitt | ||
| Space - Scott Zielinski | ||
| The Water Engine - Robert Perry | ||
| The Wild Party (Manhattan Theatre Club) - Kenneth Posner | ||
| Outstanding Sound Design | Charlie Victor Romeo - Jamie Mereness | |
| Chesapeake - Darron L. West | ||
| Coyote on a Fence - Marc Gwinn | ||
| Space - Rob Milburn, Michael Bodeen | ||
| Y2K - Darron L. West | ||
| Outstanding Solo Performance | Olympia Dukakis - Rose Marc | |
| Spalding Gray - Morning, Noon and Night | ||
| Barry Humphries - Dame Edna: The Royal Tour | ||
| Mark Linn-Baker - Chesapeake | ||
| Mark Setlock - Fully Committed | ||
| Wolf - Another American: Asking and Telling | ||
| Outstanding Unique Theatrical Experience | Charlie Victor Romeo | |
| Do You Come Here Often? | ||
| Shockheaded Peter | ||
| Special Awards | Alexander H. Cohen (posthumous) | |
| Outstanding Ensemble Performance | Cast of "Jitney" | |
| Lifetime Achievement Award | Barnard Hughes | |
| Helen Stenborg |
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