| Drama Desk Award for Outstanding Direction of a Musical | |
|---|---|
|    Michael Arden, 2025 winner | |
| Awarded for | Outstanding Direction of a Musical | 
| Location | New York City | 
| Country | United States | 
| Presented by | Drama Desk | 
| First award | 1975 | 
| Currently held by | Michael Arden for Maybe Happy Ending (2025) | 
| Website | dramadesk.org (defunct) | 
The Drama Desk Award for Outstanding Direction of a Musical is an annual award presented by Drama Desk in recognition of achievements in theatre across collective Broadway, off-Broadway and off-off-Broadway productions in New York City. The awards were established in 1955, with the Drama Desk Award for Outstanding Director being presented each year to a director from any play or musical production. Starting in 1975, the singular director's award was replaced by separate play and musical categories.
Harold Prince holds the record for most wins in the category, with four, followed closely by Tommy Tune and Michael Mayer with three wins each. Prince is also tied with John Doyle for the most nominations in the category, both with eight.
| Year | Director | Production | 
|---|---|---|
| 1980 | ||
| Harold Prince | Evita | |
| Walton Jones | 1940's Radio Hour | |
| Joe Layton | Barnum | |
| Gary Pearle | Tintypes | |
| 1981 | ||
| Wilford Leach | The Pirates of Penzance | |
| Arthur Faria | Lena Horne: The Lady and Her Music | |
| 1982 | ||
| Tommy Tune | Nine | |
| Michael Bennett | Dreamgirls | |
| Tony Tanner | Joseph and the Amazing Technicolor Dreamcoat | |
| 1983 | ||
| George Abbott | On Your Toes | |
| Howard Ashman | Little Shop of Horrors | |
| 1984 | ||
| James Lapine | Sunday in the Park with George | |
| A.J. Antoon | The Rink | |
| Jacques Levy | Doonesbury | |
| 1985 | — | |
| 1986 | ||
| Wilford Leach | The Mystery of Edwin Drood | |
| Andre Ernotte | Goblin Market | |
| Bob Fosse | Big Deal | |
| Sweet Charity | ||
| Paul Lazarus | Personals | |
| 1987 | ||
| Mike Ockrent | Me and My Girl | |
| Barry Harman | Olympus on My Mind | |
| 1988 | ||
| Harold Prince | The Phantom of the Opera | |
| James Lapine | Into the Woods | |
| Harold Prince | Cabaret | |
| Jerry Zaks | Anything Goes | |
| 1989 | — | |
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