By Bethany Ortiz, Senior Correspondent
The 69th Annual Drama Desk Awards took place on June 1, 2025, at NYU Skirball in Manhattan, co-hosted by Debra Messing and Tituss Burgess. The event honored standout productions and performances across Broadway, Off-Broadway, and Off-Off-Broadway. Branden Jacobs-Jenkins’ Purpose won Outstanding Play, while Maybe Happy Ending took Outstanding Musical, securing multiple accolades including direction and scenic design. Notable individual winners included Audra McDonald and Jasmine Amy Rogers for lead musical performances.
A Night of Theatrical Triumphs
The Drama Desk Awards, known for recognizing excellence across all levels of New York theater, showcased a diverse array of talent this year. The ceremony celebrated both emerging voices and seasoned performers, reflecting the vibrancy of the current theater landscape.
From innovative storytelling to powerful performances, the night served as a tribute to the creativity and resilience of the theatrical community. As the industry continues to rebound from the challenges of recent years, this year’s awards were a testament to its enduring spirit.
Major Winners
- Outstanding Play: Purpose by Branden Jacobs-Jenkins
- Outstanding Musical: Maybe Happy Ending
- Outstanding Revival of a Play: Eureka Day
- Outstanding Revival of a Musical: Gypsy
Purpose, a compelling family drama exploring themes of legacy and identity, has garnered widespread acclaim. Its win at the Drama Desk Awards further solidifies its place as a powerful narrative in contemporary theater.
Maybe Happy Ending, a touching musical about unexpected love and connection, was another standout. With its inventive score and evocative set design, it captured the hearts of both audiences and critics.
Individual Honors
- Outstanding Lead Performance in a Musical:
- Audra McDonald for Gypsy
- Jasmine Amy Rogers for BOOP! The Musical
- Outstanding Featured Performance in a Play:
- Amalia Yoo for John Proctor is the Villain
- Kara Young for Purpose
- Outstanding Featured Performance in a Musical:
- Brooks Ashmanskas for Smash
- Jak Malone for Operation Mincemeat
- Michael Urie for Once Upon a Mattress
These performances highlighted the depth of talent present in this year’s theatrical productions. Each actor brought a distinct energy and perspective to their role, enriching the overall theatrical experience.
Creative and Technical Achievements
- Outstanding Direction of a Play: Danya Taymor for John Proctor is the Villain
- Outstanding Direction of a Musical: Michael Arden for Maybe Happy Ending
- Outstanding Book of a Musical: Will Aronson and Hue Park for Maybe Happy Ending
- Outstanding Scenic Design of a Musical: Dane Laffrey and George Reeve for Maybe Happy Ending
These accolades recognize the vision and innovation of the creative teams. From set design to musical arrangement, each element played a crucial role in bringing stories to life on stage.
Special Recognitions
The Drama Desk Awards also honored individuals and ensembles for their exceptional contributions to theater:
- Harold S. Prince Award for Lifetime Achievement: Gavin Creel (posthumously)
- William Wolf Award: Brian Stokes Mitchell
- Ensemble Award: The cast of Liberation
These special awards underscored the enduring impact of these artists and their dedication to advancing the art of theater.
Looking Ahead
With the Tony Awards on the horizon, many of this year’s Drama Desk winners are expected to continue their success. Productions like Purpose and Maybe Happy Ending have not only achieved critical acclaim but have also sparked meaningful conversations among theatergoers.
This year’s Drama Desk Awards offered a hopeful glimpse into the future of American theater—one that embraces diversity, innovation, and heartfelt storytelling. The evening was more than a celebration of past achievements; it was an affirmation of theater’s vital role in cultural expression and community engagement.