Who took home the most Drama Desk Trophies—and why?
The 2025 Drama Desk Awards dazzled New York City's theatre community with a night of celebration, surprises, and record-breaking victories at
NYU Skirball
, hosted by the dynamic duo
Debra Messing
and Tituss Burgess. The ceremony—now in its 69th year—remains unique for recognizing the best of Broadway, Off-Broadway, and Off-Off-Broadway in the same competitive categories, making it a true barometer of New York's theatrical pulse.
Leading the winners' parade was
Maybe Happy Ending
, which swept six awards. The show's creative team is led by director Michael Arden and writers Will Aronson and Hue Park. The musical, also a current Tony nominee for Best Musical, was widely celebrated for its innovative storytelling and emotional resonance.
Debra Messing, co-hosting the event, remarked, 'Tonight is a celebration of the resilience, creativity, and passion that define New York theatre.' The Drama Desk Awards once again proved why they are a highlight of the theatrical calendar, honoring both established stars and rising talents in a night of unforgettable performances and heartfelt speeches.'
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69th Drama Desk Awards: major winners
1. Outstanding Musical
Winner:
Maybe Happy Ending
2. Outstanding Play
Live Events
Winner:
Purpose
(by Branden Jacobs-Jenkins)
3. Outstanding Revival of a Play
Winner:
Eureka Day
4. Outstanding Revival of a Musical
Winner:
Gypsy
5. Leading Performance in a Musical
Winners:
Jasmine Amy Rogers (
BOOP! The Musical
)
Audra McDonald (
Gypsy
) (TIE)
6. Featured Performance in a Musical
Winners:
Brooks Ashmanskas (
Smash
)
Jak Malone (
Operation Mincemeat
)
Michael Urie (
Once Upon a Mattress
) (THREE-WAY TIE)
7. Outstanding Director of a Musical
Winner: Michael Arden (
Maybe Happy Ending
)
8. Outstanding Music, Lyrics, and Book
Winners: Will Aronson & Hue Park (
Maybe Happy Ending
)
9. Outstanding Choreography
Winner: Jerry Mitchell (
BOOP! The Musical
)
10. Outstanding Costume Design
Winner: Gregg Barnes (
BOOP! The Musical
)
11. Outstanding Scenic Design
Winner:
Maybe Happy Ending
(team/designer not specified in summary)
12. Additional Notable Winners (Design/Staging)
Stranger Things: The First Shadow (3 awards, categories not specified)
The Picture of Dorian Gray (3 awards, categories not specified)
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