1999-2000 Awards
| Award | Winner(s) | Nominee(s) |
|---|---|---|
| John Gassner Playwriting Award | Charles Busch The Tale of the Allergist’s Wife | David Lindsay-Abaire Fuddy Meers Kenneth Lonergan The Waverly Gallery Joan Vail Thorne The Exact Center of the Universe |
| Outstanding Actor in a Musical | Brian Stokes Mitchell Kiss Me Kate | Craig Bierko The Music Man James Carpinello Saturday Night Fever Taye Diggs The Wild Party |
| Outstanding Actor in a Play | Derek Jacobi Uncle Vanya | Stephen Dillane The Real Thing Michael Sheen Amadeus David Suchet Amadeus |
| Outstanding Actress in a Musical | Marin Mazzie Kiss Me Kate | Toni Collette The Wild Party Heather Headley Aida Rebecca Luker The Music Man |
| Outstanding Actress in a Play | Eileen Heckart The Waverly Gallery | Rosemary Harris Waiting in the Wings Laura Linney Uncle Vanya J. Smith-Cameron Fuddy Meers |
| Outstanding Broadway Musical | Contact | James Joyce’s The Dead Saturday Night Fever Swing! |
| Outstanding Broadway Play | Copenhagen | The Green Bird True West Waiting in the Wings |
| Outstanding Choreography | Susan Stroman Contact / The Music Man | Mark Dendy The Wild Party Kathleen Marshall Kiss Me Kate Lynne Taylor-Corbett Swing! |
| Outstanding Costume Design | Constance Hoffman The Green Bird | William Dudley Amadeus William Ivey Long The Music Man Martin Pakledinaz Kiss Me Kate |
| Outstanding Director of a Musical | Susan Stroman Contact / The Music Man | Gabriel Barre The Wild Party Michael Blakemore Kiss Me Kate Richard Nelson James Joyce’s The Dead |
| Outstanding Director of a Play (The Lucille Lortel Award) | Daniel Sullivan Dinner with Friends / A Moon for the Misbegotten | Michael Blakemore Copenhagen Peter Hall Amadeus David Leveaux The Real Thing |
| Outstanding Featured Actor in a Musical | Stephen Spinella James Joyce’s The Dead | Michael Berresse Kiss Me Kate Boyd Gaines Contact Tony Vincent Jesus Christ Superstar |
| Outstanding Featured Actor in a Play | Roy Dotrice A Moon for the Misbegotten | Bob Dishy The Price Daniel Gerroll An Experiment with an Air Pump Simon Jones Waiting in the Wings |
| Outstanding Featured Actress – Musical | Karen Ziemba Contact | Blair Brown James Joyce’s The Dead Ruth Williamson The Music Man Deborah Yates Contact |
| Outstanding Featured Actress in a Play | Frances Conroy The Ride Down Mt. Morgan | Jennifer Ehle The Real Thing Cindy Katz Amadeus Lizbeth Mackay The Price |
| Outstanding Lighting Design | Peter Kaczorwoski Contact | Paule Constable Amadeus Donald Holder The Green Bird Kenneth Posner The Wild Party |
| Outstanding Off Broadway Play | Dinner with Friends | An Experiment with an Air Pump Dirty Blonde The Tale of the Allergist’s Wife |
| Outstanding Off-Broadway Musical | The Wild Party | After the Fair Jolson & Co. The Bomb-Itty of Errors |
| Outstanding Revival of a Musical | Kiss Me Kate | Jesus Christ Superstar Putting It Together The Music Man |
| Outstanding Revival of a Play | A Moon for the Misbegotten | Amadeus The Real Thing Uncle Vanya |
| Outstanding Scenic Design | Robin Wagner Kiss Me Kate | John Lee Beatty An Experiment with an Air Pump William Dudley Amadeus Thomas Lynch The Music Man |
| Outstanding Solo Performance | Olympia Dukakis Rose Mark Setlock Fully Committed | Mark Linn-Baker Chesapeake Marc Wolf Another American Asking and Telling |
| Special Awards | Barry Humphries Dame Edna: The Royal Tour Philip Seymour Hoffman, John C. Reilly True West |
