1987-1988 34th Drama Desk Awards
| Outstanding Actor - Musical | David Carroll (Chess) | |
| Michael Crawford (Phantom of the Opera) | ||
| Howard McGillin (Anything Goes) | ||
| George Merritt (Lost in the Stars) | ||
| Outstanding Actor - Play | Derek Jacobi (Breaking the Code) | |
| Delroy Lindo (Joe Turner's Come and Gone) | ||
| John Lithgow (M Butterfly) | ||
| John Malkovich (Burn This) | ||
| Joe Mantegna (Speed the Plow) | ||
| Ron Silver (Speed the Plow) | ||
| Outstanding Actress - Musical | Sarah Brightman (Phantom of the Opera) | |
| Judy Kuhn (Chess) | ||
| Patti LuPone (Anything Goes) | ||
| Bernadette Peters (Into the Woods) | ||
| Outstanding Actress - Play | Kathy Bates (Frankie and Johnny in the Claire de Lune) | |
| Stockard Channing (Women in Mind) | ||
| Amy Irving (The Road to Mecca) | ||
| Glenda Jackson (Macbeth) | ||
| E. Katherine Kerr (Laughing Wild) | ||
| Gordana Rashovich (Shayna Maidel) | ||
| Outstanding Book of a Musical | James Lapine (Into the Woods) | |
| Outstanding Choreography | Grover Dale (Mail) | |
| Gillian Lynne (Phantom of the Opera) | ||
| Michael Smuin (Anything Goes) | ||
| Outstanding Costume Design | Maria Bjornson (Phantom of the Opera) | |
| Eiko Ishioka (M Butterfly) | ||
| Ann Hould-Ward (Into the Woods) | ||
| Tony Walton (Anything Goes) | ||
| Outstanding Director - Musical | James Lapine (Into the Woods) | |
| Harold Prince (Cabaret) | ||
| Harold Prince (Phantom of the Opera) | ||
| Jerry Zaks (Anything Goes) | ||
| Outstanding Director - Play | John Dexter (M Butterfly) | |
| W.H. Macy (Boy's Life) | ||
| Lynne Meadow (Women in Mind) | ||
| Gregory Mosher (Speed the Plow) | ||
| Lloyd Richards (Joe Turner's Come and Gone) | ||
| Outstanding Ensemble Performance | Boy's Life | |
| The Day Room | ||
| Oil City Symphony | ||
| Outstanding Featured Actor - Musical | Harry Goz (Chess) | |
| Anthony Heald (Anything Goes) | ||
| Bill McCutcheon (Anything Goes) | ||
| Herbert Rawlings (Dreamgirls) | ||
| Robert Westenberg (Into the Woods) | ||
| Outstanding Featured Actor - Play | Athol Fugard (The Road to Mecca) | |
| Michael Gough (Breaking the Code) | ||
| Joe Grifasi (Boys Next Door) | ||
| Ed Hall (Joe Turner's Come and Gone) | ||
| Lou Liberatore (Burn This) | ||
| B.D. Wong (M Butterfly) | ||
| Outstanding Featured Actress - Musical | Danielle Ferland (Into the Woods) | |
| Joanna Gleason (Into the Woods) | ||
| Lyn Greene (Flora the Red Menace) | ||
| Judy Kaye (Phantom of the Opera) | ||
| Outstanding Featured Actress - Play | Kimberleigh Aarn (Joe Turner's Come and Gone) | |
| Christine Estabrook (Boys Next Door) | ||
| Frances McDormand (A Streetcar Named Desire) | ||
| Kimberly Scott (Joe Turner's Come and Gone) | ||
| Outstanding Lighting Design | Andrew Bridge (Phantom of the Opera) | |
| Pat Collins (Women in Mind) | ||
| Paul Gallo (Anything Goes / Wenceslas Square) | ||
| David Hersey (Chess) | ||
| Richard Nelson (Into the Woods) | ||
| Outstanding Lyrics | Barry Harman (Romance, Romance) | |
| Stephen Sondheim (Into the Woods) | ||
| Outstanding Music | Benny Andersson, Bjorn Ulvaeus (Chess) | |
| David Evans (Birds of Paradise) | ||
| Hugh Masekela, Mbongeni Ngema (Sarafina) | ||
| Stephen Sondheim (Into the Woods) | ||
| Andrew Lloyd Webber (Phantom of the Opera) | ||
| Outstanding Musical | Into the Woods | |
| Phantom of the Opera | ||
| Outstanding New Play | Boy's Life (Howard Korder) | |
| Joe Turner's Come and Gone (August Wilson) | ||
| M Butterfly (David Henry Hwang) | ||
| The Road to Mecca (Athol Fugard) | ||
| Speed the Plow (David Mamet) | ||
| Women in Mind (Alan Ayckbourn) | ||
| Outstanding One Person Show | Barbara Cook (A Concert for the Theatre) | |
| Outstanding Orchestration | David Cullen, Andrew Lloyd Webber (Phantom of the Opera) | |
| Michael Gibson (Anything Goes) | ||
| Michael Starobin (Birds of Paradise) | ||
| Jonathan Tunick (Into the Woods) | ||
| Outstanding Revival | Anything Goes | |
| Cabaret | ||
| Dreamgirls | ||
| Flora the Red Menace | ||
| Lost in the Stars | ||
| Outstanding Set Design | Maria Bjornson (Phantom of the Opera) | |
| Scott Bradley (Joe Turner's Come and Gone) | ||
| Eiko Ishioka (M Butterfly) | ||
| Tony Straiges (Into the Woods) | ||
| Tony Walton (Anything Goes) | ||
| Special Awards | The Yale Repertory Theatre | |
| Actors Equity Association | ||
| Michael Feinstein | ||
| The Theatre on Film and Tape Collection |
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