The Drama Desk, a group of 150 theater critics and reporters, announced the awards on May 18, 2003.
| Outstanding Play | Take Me Out |
| Outstanding Musical | Hairspray |
| Outstanding Musical Revival | Nine |
| Outstanding Play Revival | Long Day's Journey Into Night |
| Best Actor in a Play | Eddie Izzard, A Day in the Death of Joe Egg |
| Best Actress in a Play | Vanessa Redgrave, Long Day's Journey Into Night |
| Best Featured Actor in a Play | Denis O'Hare, Take Me Out |
| Best Featured Actress in a Play | Lynn Redgrave, Talking Heads |
| Best Actor in a Musical (tie) | Antonio Banderas, Nine and Harvey Fierstein, Hairspray |
| Best Actress in a Musical | Marissa Jaret Winokur, Hairspray |
| Best Featured Actor in a Musical | Dick Latessa, Hairspray |
| Best Featured Actress in a Musical | Jane Krakowski, Nine |
| Best Director of a Play | Robert Falls, Long Day's Journey Into Night |
| Best Director of a Musical | Jack O'Brien, Hairspray |
| Best Choreography | Twyla Tharp, Movin' Out |
| Best Book of a Musical | Mark O'Donnell and Thomas Meehan, Hairspray |
| Best Music | Marc Shaiman, Hairspray |
| Best Lyrics | Scott Wittman and Marc Shaiman, Hairspray |
| Outstanding Orchestrations | Harold Wheeler, Hairspray |
| Outstanding Set Design of a Play | John Lee Beatty, Dinner at Eight |
| Outstanding Set Design of a Musical | Catherine Martin, La Boheme |
| Outstanding Costume Design | William Ivey Long, Hairspray |
| Outstanding Lighting Design | Nigel Levings, La Boheme |
| Outstanding Sound Design | Acme Sound Partners, La Boheme |
| Outstanding Solo Performance | Tovah Feldshuh, Golda's Balcony |
| Unique Theatrical Experience | The Exonerated |
| Special Awards | Brooklyn Academy of Music for bringing works of distinction from around the world to New York audiences |
| Charles Busch for career achievement as performer and playwright |
| Geoffrey Johnson and Vincent Liff (posthumous) of Johnson-Liff Casting for career achievement |
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