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The 45th Annual Drama Desk Awards presented by The Drama Desk at the [unknown venue], May 14, 2000
 
2000 Drama Desk Award Outstanding New Play
 The Ensemble Studio Theatre (Curt Dempster: Artistic Director) for "Contact with the Enemy" [nominee]
 Frank D. Gilroy for "Contact with the Enemy" [nominee]
 Donald Margulies for "Dinner with Friends" [nominee]
 Mark Balsam for "Dinner with Friends" [nominee]
 Victoria Maxwell for "Dinner with Friends" [nominee]
 Mitchell Maxwell for "Dinner with Friends" [nominee]
 Mari Nakachi for "Dinner with Friends" [nominee]
 Ted Tulchin for "Dinner with Friends" [nominee]
 August Wilson for "Jitney" [nominee]
 Alexander Fraser for "Jitney" [nominee]
 Center Theatre Group / Mark Taper Forum (Gordon Davidson, Artistic Director; Charles Dillingham, Managing Director) for "Jitney" [nominee]
 Sageworks (Benjamin Mordecai, Executive Producer; August Wilson) for "Jitney" [nominee]
 Second Stage Theatre (Carole Rothman: artistic director; Carol Fishman: managing director) for "Jitney" [nominee]
Copenhagen [winner]
  Produced by James M. Nederlander, Roger Berlind, Scott Rudin, Elizabeth Ireland McCann, Ray Larsen, Jon B. Platt, Byron Goldman, Scott Nederlander; Produced by arrangement with The Royal National Theatre (Trevor Nunn, Director), Michael Codron, Lee Dean; Written by Michael Frayn
 Dirty Blonde [nominee]
  Produced by The Shubert Organization (Gerald Schoenfeld: Chairman; Philip J. Smith: President; Robert E. Wankel: Executive Vice President), Chase Mishkin, OSTAR Enterprises, ABC, Inc.; Produced in association with New York Theatre Workshop; Written by Claudia Shear
 The Tale of the Allergist's Wife [nominee]
  Produced by Manhattan Theatre Club (Lynne Meadow, Artistic Director; Barry Grove, Executive Producer); Written by Charles Busch
 
2000 Drama Desk Award Outstanding New Musical
 Second Stage Theatre (Carole Rothman: artistic director; Carol Fishman: managing director) for "Saturday Night" [nominee]
 Manhattan Theatre Club (Lynne Meadow, Artistic Director; Barry Grove, Executive Producer) for "The Wild Party" [nominee]
Contact [winner]
  Produced by Lincoln Center Theater (André Bishop: Artistic Director; Bernard Gersten: Executive Producer)
 James Joyce's The Dead [nominee]
  Produced by Gregory Mosher, Arielle Tepper
 Swing! [nominee]
  Produced by Marc Routh, Richard Frankel, Steven Baruch, Thomas Viertel, Lorie Cowen Levy, Stanley Shopkorn, Jujamcyn Theaters (James H. Binger: Chairman; Rocco Landesman: President; Paul Libin: Producing Director; Jack Viertel: Creative Director); Produced in association with BB Promotion, Dede Harris, Jeslo Productions, Libby Adler Mages, Mari Glick, Douglas L. Meyer, James D. Stern, PACE Theatrical Group, Inc., SFX Entertainment, Inc.
 
2000 Drama Desk Award Outstanding Revival of a Play
 Theatre for a New Audience (Jeffrey Horowitz, Artistic Director) for "Waste" [nominee]
The Real Thing [winner]
  Produced by Anita Waxman, Elizabeth Williams, Ron Kastner, Miramax Films
 A Moon for the Misbegotten [nominee]
  Produced by Elliot Martin, Chase Mishkin, Max Cooper, Jujamcyn Theaters (James H. Binger: Chairman; Rocco Landesman: President; Paul Libin: Producing Director; Jack Viertel: Creative Director); Produced in association with Anita Waxman, Elizabeth Williams, The Goodman Theatre (Robert Falls, Artistic Director; Roche Schulfer, Executive Director)
 The Price [nominee]
  Produced by David Richenthal
 True West [nominee]
  Produced by Ron Kastner
 Uncle Vanya [nominee]
  Produced by The Roundabout Theatre Company (Todd Haimes: Artistic Director; Ellen Richard: Managing Director; Julia C. Levy: Executive Director of External Affairs; Gene Feist: Founding Director)
 
2000 Drama Desk Award Outstanding Revival of a Musical
Kiss Me, Kate [winner]
  Produced by Roger Berlind, Roger Horchow
 The Music Man [nominee]
  Produced by Dodger Theatricals (Des McAnuff, Michael David, Rocco Landesman, Doug Johnson, Robin De Levita, Ed Strong, Sherman Warner), The John F. Kennedy Center for the Performing Arts, Elizabeth Williams, Anita Waxman, Kardana-Swinsky Productions, Lorie Cowen Levy, Dede Harris
 
2000 Drama Desk Award Outstanding Actor in a Play
 Paul Sparks for "Coyote on a Fence" [nominee]
Stephen Dillane for The Real Thing [winner]
 Gabriel Byrne for A Moon for the Misbegotten [nominee]
 Kevin Chamberlin for Dirty Blonde [nominee]
 Philip Seymour Hoffman for True West [nominee]
 Derek Jacobi for Uncle Vanya [nominee]
 
2000 Drama Desk Award Outstanding Actress in a Play
 Sinéad Cusack for "Our Lady of Sligo" [nominee]
Eileen Heckart for "The Waverly Gallery" [winner]
 Lynne Thigpen for "Jar the Floor" [nominee]
 Charlaine Woodard for "In the Blood" [nominee]
 Claudia Shear for Dirty Blonde [nominee]
 Linda Lavin for The Tale of the Allergist's Wife [nominee]
 
2000 Drama Desk Award Outstanding Actor in a Musical
 Brian d'Arcy James for "The Wild Party" (MTC) [nominee]
Brian Stokes Mitchell for Kiss Me, Kate [winner]
 Boyd Gaines for Contact [nominee]
 Craig Bierko for The Music Man [nominee]
 Mandy Patinkin for The Wild Party [nominee]
 
2000 Drama Desk Award Outstanding Actress in a Musical
 Julia Murney for "The Wild Party" (MTC) [nominee]
Heather Headley for Aida [winner]
 Marin Mazzie for Kiss Me, Kate [nominee]
 Audra McDonald for Marie Christine [nominee]
 Rebecca Luker for The Music Man [nominee]
 Toni Collette for The Wild Party [nominee]
 
2000 Drama Desk Award Outstanding Featured Actor in a Play
 Matthew Arkin for "Dinner with Friends" [nominee]
 Joel Grey for "Give Me Your Answer, Do!" [nominee]
 Philip Seymour Hoffman for "The Author's Voice" [nominee]
Roy Dotrice for A Moon for the Misbegotten [winner]
 Harris Yulin for The Price [nominee]
 Brian Murray for Uncle Vanya [nominee]
 
2000 Drama Desk Award Outstanding Featured Actress in a Play
 Jillian Armenante for "The Cider House Rules, Part One" [nominee]
Marylouise Burke for "Fuddy Meers" [winner]
 Seana Kofoed for "An Experiment with an Air Pump" [nominee]
 Phyllis Newman for "The Moment When" [nominee]
 Cigdem Onat for "The Time of the Cuckoo" [nominee]
 Amy Sedaris for "The Country Club" [nominee]
 
2000 Drama Desk Award Outstanding Featured Actor in a Musical
 Christopher Fitzgerald for "Saturday Night" [nominee]
Stephen Spinella for James Joyce's The Dead [winner]
 Jason Antoon for Contact [nominee]
 Alistair Izobell for Kat and the Kings [nominee]
 Michael Mulheren for Kiss Me, Kate [nominee]
 Lee Wilkof for Kiss Me, Kate [nominee]
 
2000 Drama Desk Award Outstanding Featured Actress in a Musical
 Nancy Anderson for "Jolson and Co." [nominee]
 Alix Korey for "The Wild Party" (MTC) [nominee]
 Idina Menzel for "The Wild Party" (MTC) [nominee]
Karen Ziemba for Contact [winner]
 Sally Ann Howes for James Joyce's The Dead [nominee]
 Eartha Kitt for The Wild Party [nominee]
 
2000 Drama Desk Award Outstanding Director of a Play
 Thomas Hulce for "The Cider House Rules, Part One" [nominee]
 Jane Jones for "The Cider House Rules, Part One" [nominee]
 Marion McClinton for "Jitney" [nominee]
 Daniel Sullivan for "Dinner with Friends" [nominee]
Michael Blakemore for Copenhagen [winner]
 James Lapine for Dirty Blonde [nominee]
 Michael Mayer for Uncle Vanya [nominee]
 
2000 Drama Desk Award Outstanding Director of a Musical
 Gabriel Barre for "The Wild Party" (MTC) [nominee]
Michael Blakemore for Kiss Me, Kate [winner]
 Susan Stroman for Contact [nominee]
 Susan Stroman for The Music Man [nominee]
 
2000 Drama Desk Award Outstanding Choreography
 Mark Dendy for "The Wild Party" (MTC) [nominee]
Susan Stroman for Contact [winner]
 Jody J. Abrahams for Kat and the Kings [nominee]
 Loukmaan Adams for Kat and the Kings [nominee]
 Kathleen Marshall for Kiss Me, Kate [nominee]
 Lynne Taylor-Corbett for Swing! [nominee]
 Susan Stroman for The Music Man [nominee]
 
2000 Drama Desk Award Outstanding Music
 Stephen Sondheim for "Saturday Night" [nominee]
Andrew Lippa for "The Wild Party" (MTC) [winner]
 Shaun Davey for James Joyce's The Dead [nominee]
 
2000 Drama Desk Award Outstanding Lyrics
 Boyd Graham for "The Big Bang" [nominee]
 Erik Weiner for "The Bomb-itty of Errors" [nominee]
 Jordan Allen-Dutton for "The Bomb-itty of Errors" [nominee]
 Jason Catalano for "The Bomb-itty of Errors" [nominee]
 Gregory Qaiyum for "The Bomb-itty of Errors" [nominee]
Stephen Sondheim for "Saturday Night" [winner]
 Andrew Lippa for "The Wild Party" (MTC) [nominee]
 
2000 Drama Desk Award Outstanding Orchestrations
 Jonathan Tunick for "Saturday Night" [nominee]
 Michael Gibson for "The Wild Party" (MTC) [nominee]
Don Sebesky for Kiss Me, Kate [winner]
 Taliep Petersen for Kat and the Kings [nominee]
 Harold Wheeler for Swing! [nominee]
 Doug Besterman for The Music Man [nominee]
 
2000 Drama Desk Award Outstanding Set Design of a Play
 Neil Patel for "Dinner with Friends" [nominee]
 Derek McLane for "East is East" [nominee]
 Rob Odorisio for "An Empty Plate in the Cafe du Grand Boeuf" [nominee]
David Gallo for "Jitney" [winner]
 James Noone for "The Time of the Cuckoo" [nominee]
 Tony Walton for Uncle Vanya [nominee]
 
2000 Drama Desk Award Outstanding Set Design of a Musical
 Julian Crouch for "Shockheaded Peter" [nominee]
 Graeme Gilmour for "Shockheaded Peter" [nominee]
 David Gallo for "The Wild Party" (MTC) [nominee]
Robin Wagner for Kiss Me, Kate [winner]
 Thomas Lynch for Contact [nominee]
 Thomas Lynch for The Music Man [nominee]
 
2000 Drama Desk Award Outstanding Costume Design
 Boyd Graham for "The Big Bang" [nominee]
 Jonathan Bixby for "The Country Club" [nominee]
 Gregory Gale for "The Country Club" [nominee]
 Kevin Pollard for "Shockheaded Peter" [nominee]
 Martin Pakledinaz for "The Wild Party" (MTC) [nominee]
Martin Pakledinaz for Kiss Me, Kate [winner]
 William Ivey Long for The Music Man [nominee]
 
2000 Drama Desk Award Outstanding Lighting Design
 Brian MacDevitt for "An Experiment with an Air Pump" [nominee]
 Scott Zielinski for "Space" [nominee]
 Robert Perry for "The Water Engine" [nominee]
 Kenneth Posner for "The Wild Party" (MTC) [nominee]
Peter Kaczorowski for Contact [winner]
 David J. Lander for Dirty Blonde [nominee]
 
2000 Drama Desk Award Outstanding Sound Design
Jamie Mereness for "Charlie Victor Romeo" [winner]
 Darron L. West for "Chesapeake" and "Y2K" (2 nominations) [nominee]
 Marc Gwinn for "Coyote on a Fence" [nominee]
 Rob Milburn for "Space" [nominee]
 Michael Bodeen for "Space" [nominee]
 
2000 Drama Desk Award Outstanding Solo Performance
 Mark Linn-Baker for "Chesapeake" [nominee]
 Mark Setlock for "Fully Committed" [nominee]
 Marc Wolf for "Another American: Asking and Telling" [nominee]
Dame Edna Everage for Dame Edna: The Royal Tour [winner] ( a.k.a. Barry Humphries )
 Spalding Gray for Morning, Noon and Night [nominee]
 Olympia Dukakis for Rose [nominee]
 
2000 Drama Desk Award Unique Theatrical Experience
The Collective Unconscious for "Charlie Victor Romeo" [winner]
 Sean Foley for "Do You Come Here Often?" [nominee]
 Hamish McColl for "Do You Come Here Often?" [nominee]
 New Victory Theatre for "Shockheaded Peter" [nominee]
 
2000 Drama Desk Award Outstanding Ensemble Performance
Willis Burks II for "Jitney" [winner]
Paul Butler for "Jitney" [winner]
Anthony Chisholm for "Jitney" [winner]
Leo V. Finnie III for "Jitney" [winner]
Stephen McKinley Henderson for "Jitney" [winner]
Barry Shabaka Henley for "Jitney" [winner]
Russell Hornsby for "Jitney" [winner]
Carl Lumbly for "Jitney" [winner]
Michole Briana White for "Jitney" [winner]
 
2000 Drama Desk Award Special Award
Alexander H. Cohen Lifetime Achievement (posthumously) [recipient]
Barnard Hughes Lifetime Achievement [recipient]
Helen Stenborg Lifetime Achievement [recipient]