The 2004–2005 Obie Awards, honoring distinguished achievement in Off-Broadway and Off-Off-Broadway productions, were presented on May 16, 2005, at New York's Webster Hall.
| Direction: | Dan Wackerman, Counsellor-At-Law; |
| Ivo van Hove, Hedda Gabler; |
| Doug Hughes for sustained excellence of direction |
| Performance: | Jeremy Shamos, Engaged; |
| Elizabeth Marvel, Hedda Gabler; |
| Jason Butler Harner, Hedda Gabler; |
| Rosemary Allen, Good Samaritans; |
| Cherry Jones, Doubt; |
| Larry Bryggman, Romance; |
| Kieran Culkin, After Ashley; |
| Mercedes Ruehl, Woman Before A Glass; |
| LaChanze, Dessa Rose; |
| Deidre O'Connell for her sustained excellence of performance |
| Vivienne Benesch, Going to St. Ives; |
| L. Scott Caldwell, Going to St. Ives |
| Design: | John Lee Beatty, set design Engaged; |
| Rui Rita, lighting design Engaged; |
| Aural Fixation Sound & Music, sound design Engaged; |
| Catherine Zuber, costume design Engaged; |
| Thomas Lynch, set design Woman Before A Glass; |
| Phil Monat, lighting design Woman Before A Glass; |
| David Van Tieghem, sound design Woman Before A Glass; |
| Willa Kim, costume design Woman Before A Glass; |
| Jan Versweyveld, set design Hedda Gabler |
| Playwriting: | Christopher Shinn, Where Do We Live; |
| John Patrick Shanley, Doubt; |
| Caryl Churchill, A Number; |
| Lynn Nottage, Fabulation |
| Special Citations: | The Imagine Festival of Arts, Issues & Ideas; |
| Hell Meets Henry Halfway; |
| Sin: A Cardinal Deposed |
| Sustained Achievement: | John Guare |
| Grants: | 13P, Epic Theatre Company, Little Theater at Tonic, Gina Gionfriddo for Distinguished Emerging Playwright, Margo Skinner Memorial Acting Scholarship |
| Ross Wetzsteon Award: | New Dramatists |
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