2003-2004 49th Drama Desk Awards
| Outstanding Play | The Beard of Avon | |
| The Distance From Here | ||
| Humble Boy | ||
 |
I Am My Own Wife | |
| Moby Dick (Works Productions) | ||
| The Tricky Part | ||
| Outstanding Musical | Caroline, or Change | |
| Johnny Guitar | ||
| The Musical of Musicals: The Musical | ||
| Wicked | ||
| Outstanding Revival of a Play | The Colleen Bawn | |
| The Daughter-in-Law | ||
| Henry IV (LCT) | ||
| A Midsummer Night's Dream (Watermill Theatre production from Propeller/BAM) | ||
| The Normal Heart | ||
| A Raisin in the Sun | ||
| Outstanding Revival of a Musical | Assassins | |
| Big River | ||
| Fiddler on the Roof | ||
| Finian's Rainbow | ||
| First Lady Suite | ||
| Wonderful Town | ||
| Outstanding Actor - Play | John Michael Higgins, Big Bill | |
| Kevin Kline, Henry IV | ||
| Frank Langella, Match | ||
| Brian F. O'Byrne, Frozen | ||
| Christopher Plummer, King Lear | ||
| Paul Sparks, Blackbird | ||
| Outstanding Actress - Play | Eileen Atkins, The Retreat from Moscow | |
| Shannon Cochran, Bug | ||
| Viola Davis, Intimate Apparel | ||
| Lizan Mitchell, Trojan Women | ||
| Phylicia Rashad, A Raisin in the Sun | ||
| J. Smith-Cameron, Sarah, Sarah | ||
| 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 | Kristin Chenoweth, Wicked | |
| Judy McLane, Johnny Guitar | ||
| Idina Menzel, Wicked | ||
| Donna Murphy, Wonderful Town | ||
| Elaine Paige, Sweeney Todd | ||
| Tonya Pinkins, Caroline, or Change | ||
| Outstanding Featured Actor - Play | Ned Beatty, Cat on a Hot Tin Roof | |
| Michael Berry, Moby Dick (Works Productions) | ||
| Andre De Shields, Prymate | ||
| Aidan Gillen, The Caretaker | ||
| John Lithgow, Mrs. Farnsworth | ||
| Corey Stoll, Intimate Apparel | ||
| Outstanding Featured Actress - Play | Jayne Houdyshell, Well | |
| Mikel Sarah Lambert, The Daughter-in-Law | ||
| Margo Martindale, Cat on a Hot Tin Roof | ||
| Jan Maxwell, Sixteen Wounded | ||
| Audra McDonald, A Raisin in the Sun | ||
| Mary Louise Wilson, The Beard of Avon | ||
| Outstanding Featured Actor - Musical | Joel Blum, Golf: The Musical | |
| Mitchel David Federan, The Boy From Oz | ||
| Jeffrey Carlson, Taboo | ||
| Raul Esparza, Taboo | ||
| Marc Kudisch, Assassins | ||
| Raymond Jaramillo McLeod, Wonderful Town | ||
| Outstanding Featured Actress - Musical | Lovette George, The Musical of Musicals: The Musical | |
| Isabel Keating, The Boy From Oz | ||
| Alix Korey, Listen to My Heart | ||
| Anika Noni Rose, Caroline, or Change | ||
| Jennifer Simard, The Thing About Men | ||
| Mary Testa, First Lady Suite | ||
| Outstanding Director - Play | Hilary Adams, Moby Dick (Works Productions) | |
| Dexter Bullard, Bug | ||
| Edward Hall, A Midsummer Night's Dream (Watermill Theatre production from Propeller/BAM) | ||
| Moises Kaufman, I Am My Own Wife | ||
| Kenny Leon, A Raisin in the Sun | ||
| Jack O'Brien, Henry IV (LCT) | ||
| Outstanding Director - Musical | Jeff Calhoun, Big River | |
| Pamela Hunt, The Musical of Musicals: The Musical | ||
| Joe Mantello, Assassins | ||
| Joe Mantello, Wicked | ||
| Kathleen Marshall, Wonderful Town | ||
| George C. Wolfe, Caroline, or Change | ||
| Outstanding Choreography | Stephen Hues, Ramayana 2K3 | |
| Kathleen Marshall, Wonderful Town | ||
| Jerry Mitchell, Never Gonna Dance | ||
| Anthony van Laast and Farah Khan, Bombay Dreams | ||
| Outstanding Music | RaRa Avis and Andrew Yeater, et al; Ramayana 2K3 | |
| Boy George, Taboo | ||
| Eric Rockwell, The Musical of Musicals: The Musical | ||
| Stephen Schwartz, Wicked | ||
| Martin Silvestri and Joel Higgins, Johnny Guitar | ||
| Jeanine Tesori, Caroline, or Change | ||
| Outstanding Lyrics | Joanne Bogart, The Musical of Musicals: The Musical | |
| Boy George, Taboo | ||
| Sean Hartley, Cupid and Psyche | ||
| Joel Higgins, Johnny Guitar | ||
| Stephen Schwartz, Wicked | ||
| Outstanding Book of a Musical | Winnie Holzman, Wicked | |
| Tony Kushner, Caroline, or Change | ||
| Outstanding Orhcestrations | Paul Bogaev, Bombay Dreams | |
| William David Brohn, Wicked | ||
| Michael Starobin, Assassins | ||
| Harold Wheeler, Never Gonna Dance | ||
| Outstanding Set Designs - Play | John Lee Beatty, Twentieth Century | |
| Scott Bradley, The Notebooks of Leonardo da Vinci | ||
| Ralph Funicello, Henry IV (LCT) | ||
| David Korins, Blackbird | ||
| Andrew Lieberman, Wintertime | ||
| Derek McLane, I Am My Own Wife | ||
| Outstanding Set Designs - Musical | John Lee Beatty, Wonderful Town | |
| Robert Brill, Assassins | ||
| Eugene Lee, Wicked | ||
| Tom Pye, Fiddler on the Roof | ||
| Mark Thompson, Bombay Dreams | ||
| Outstanding Costume Design | Jess Goldstein, Henry IV (LCT) Mark Thompson, Bombay Dreams | |
| Susan Hilferty, Wicked | ||
| Robert A. Prior and Lisa Leighton, Ramayana 2K3 | ||
| Jenny Mannis, Animal Farm | ||
| Catherine Zuber, Intimate Apparel | ||
| Outstanding Lighting Design | Jules Fisher and Peggy Eishenhauer, Assassins | |
| TJ Gerckens, The Notebooks of Leonardo da Vinci | ||
| Donald Holder, The Violet Hour | ||
| David Lander, I Am My Own Wife | ||
| Brian MacDevitt, Henry IV | ||
| Kenneth Posner, Wicked | ||
| Outstanding Sound Design | Mark Bennett, Henry IV (LCT) | |
| Scott Jennings, Ramayana 2K3 | ||
| Brian Ronan, Bug | ||
| Dan Moses Schreier, Assassins | ||
| David Van Tieghem, The Stendhal Syndrome | ||
| Outstanding Solo Performance | Barbara Cook, Barbara Cook's Broadway | |
| Ben Gazzara, Nobody Don't Like Yogi | ||
| Sarah Jones, Bridge and Tunnel | ||
| Jefferson Mays, I Am My Own Wife | ||
| Martin Moran, The Tricky Part | ||
| Will Power, Flow | ||
| Unique Theatrical Experience | Ramayana 2K3 | |
| Todd Robbins' Carnival Knowledge | ||
| Toxic Audio in Loud Mouth | ||
| Outstanding Ensemble Performance | The cast of "The Distance From Here" | |
| Special Awards | Dakin Matthews for his adaptation of Shakespeare's Henry IV | |
| The Flea Theatre | ||
| The Classical Theatre of Harlem |
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