The Drama Desk, a group of 150 theater critics and reporters, announced the awards on May 20, 2001
| Outstanding Play | Proof |
| Outstanding Musical | The Producers |
| Outstanding Musical Revival | 42nd Street |
| Outstanding Play Revival | Gore Vidal’s The Best Man |
| Outstanding Solo Performance | Pamela Gien, The Syringa Tree |
| Unique Theatrical Experience | Mnemonic |
| Best Actor in a Play | Richard Easton, The Invention of Love |
| Best Actress in a Play | Mary-Louise Parker, Proof |
| Best Featured Actor in a Play | Charles Brown, King Hedley II |
| Best Featured Actress in a Play | Viola Davis, King Hedley II |
| Best Actor in a Musical | Nathan Lane, The Producers |
| Best Actress in a Musical | Marla Schaffel, Jane Eyre |
| Best Featured Actor in a Musical | Gary Beach, The Producers |
| Best Featured Actress in a Musical | Cady Huffman, The Producers |
| Best Director of a Play | Jack O’Brien, The Invention of Love |
| Best Director of a Musical | Susan Stroman, The Producers |
| Best Choreography | Susan Stroman, The Producers |
| Best Music | David Yazbek, The Full Monty |
| Best Lyrics | Mel Brooks, The Producers |
| Outstanding Orchestrations | Doug Besterman, The Producers |
| Outstanding Set Design of a Play | Bob Crowley, The Invention of Love |
| Outstanding Set Design of a Musical | Robin Wagner, The Producers |
| Outstanding Costume Design | William Ivey Long, The Producers |
| Outstanding Lighting Design | Paul Anderson, Mnemonic |
| Special Awards | Sean Campion and Conleth Hill, for their performances in Stones in His Pockets |
| Reba McEntire for her performance in Annie Get Your Gun |
| The casts of Cobb and Tabletop—Outstanding Ensemble Performance |
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