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.”

69th Drama Desk Awards: major winners

1. Outstanding Musical

• Winner: Maybe Happy Ending
  

2. Outstanding Play

• 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)