Winners of six Drama Desk awards, the cast of Maybe Happy Ending. (Photo: Krystal Chocianowski & Iris Wiener)
Maybe Happy Ending topped all shows with six awards at the 2025 Drama Desk Awards, including Outstanding Musical. BOOP! The Musical, Stranger Things: The First Shadow, and The Picture of Dorian Gray won three each.
Hosted by Debra Messing and Titus Burgess, the evening marked the Drama Desk’s 69th ceremony, held on June 1 at NYU’s Skirball Center.
The awards celebrate Broadway, Off-Broadway, and Off-Off Broadway shows. All of the net proceeds from the Drama Desk Awards benefited the Entertainment Community Fund.
Winners and presenters spoke with The New York Independent to reflect on the 2024-2025 season and their unique journeys to the Drama Desk Awards.
Sarah Snook, Outstanding Lead Performance in a Play, The Picture of Dorian Gray
Sarah Snook
“I think theater is such a welcoming community. We’re a great big rag-tag band of misfits. My advice for young artists is to find your role within that troupe of misfits. It’s a wonderful experience for kids when they’re growing up. It’s something I certainly did in high school. I found my group of people who were on the fringe, played pretend, and really loved it. Whether you go into the performing side or the crew side of that, there’s always a great community at heart and a family to be found in the theater.
[My advice for young Sarah is to] keep your head down and chin up. She probably needed to get out of her own head a little bit more!”
Michael Urie, Outstanding Featured Performance in a Musical, Once Upon a Mattress
Michael Urie
“I am so surprised; it was such a stacked category and the show was open so long ago. Sometimes people are like, ‘Oh, that was this season?’ It just means a lot that the Drama Desk remembered me and honored me.
[When I began working on Mattress] I was doing two shows at once: Mattress all day and then Spamalot at night. It was a crazy time, but I was also thriving, and I was loving it. I couldn’t have been happier.
“If I could talk to Prince Dauntless now, I would say ‘It’s going to be okay. You got the girl. You got up the stairs. Everything is fine.’
“The Drama Desk is a special award because it includes all of us in the New York theater community. We’re all here, Off-Off-Broadway.
I’m still shooting [the Apple TV+ series] Shrinking, but I’m so glad I’m not shooting tomorrow so I could be here tonight!”
Kara Young, Outstanding Featured Performance in a Play, Purpose
Kara Young
“I spoke of ‘leaning in’ in my acceptance speech, and I feel like I’m doing it now as I absorb the season. It’s the first time I’ve been in a production while celebrating the success of it, going to all of the galas, the awards, and the press events.
I’m feel that I’m leaning in now because it doesn’t matter how many things you do in a day, you keep going. You go from a photo shoot, to an interview, to the show, and you might be exhausted. But once it’s half hour, you just lean in. There’s a story to tell.
Branden Jacobs-Jenkins has written something incredibly beautiful, heartbreaking, haunting, and so deep that it leaves us feeling things that we don’t understand.
When a writer does that you know that something has shifted inside of you. Every single night something has shifted inside of me and I’m always hearing the play anew.”
Jak Malone, Outstanding Featured Performance in a Musical, Operation Mincemeat
Jak Malone
“I’m having a party. New York is the place where I’ve lent into looking pretty in the most joyous way. [My evolving style is] mainly because we have so many events to attend that I have to pull outfits from somewhere. I’m taking bigger risks than I usually would, truly. Growing up, doing musical theater, I was very slim and pretty. I always played romantic lead roles. They were great, and there’s always a lot of songs there. However, they’re not a lot of fun-no silly goofs. It wasn’t until I put on weight as I got older that people went, ‘Oh, this actor is funny.’
“I was always funny! It’s a shame that people can only recognize certain elements of you if they tick a little box that they have for themselves. I’m blessed to be in a show where it doesn’t matter what you look like. I play a 50-year-old woman, I play a shoe shine boy, I do the whole gambit. It has been a really fun journey, one that I’m glad I’m on. I make no apologies for myself.
“If I could talk to Bill [a prominent character in Mincemeat], I would say, ‘I’m so sorry that you died and that we created you out of thin air only to kill you off. It seems mean, but it was for a good cause. I hope you understand that when they gave you the mission, they gave you the best possible run up to your death day in that you got to go to the theater, buy fancy jewelry, have all these cocktails, and have a wonderful time.
“It’s a crazy mission and it’s insane what they did, but they always kept joy at the heart of it. You can’t help but think about that when you’re doing this crazy show eight times each week. At least what we’re doing is joyful.”
Tom Francis, nominee, Sunset Boulevard
Tom Francis
“It’s very satisfying to give such a vulnerable performance. I feel like I finish the show and I go, ‘That felt great.’
It always feels good for my soul. Even if I mucked up, or I did something wrong, it’s just so nice to get to say those words and do that show every night.
“I love it. I don’t think about [modesty] too deeply and just go with the punches.”
Jerry Mitchell, Outstanding Choreography, BOOP! The Musical
Jerry Mitchell
“In the Chicago tryouts we didn’t have the number ‘Where is Betty?’ I created that for New York. I knew I needed a number like the opening number that made the audience feel like they were in that specific kind of musical, where they were going to get those big, classy production numbers that come from Betty’s world.
“I was thinking about what has changed over the years since first becoming a Drama Desk winner, and I think it’s how much I appreciate it.
I listened to Celia Keenan-Bolger speak about [the late] Gavin Creel, who danced in La Cage aux Folles for me, which got me my first Drama Desk Award.
Gavin and I did a lot of work together for Broadway Cares/Equity Fights AIDS. Because of all of this I built a community where dancers could be seen. That’s what I appreciate.”
Branden Jacobs-Jenkins, Outstanding Play, Purpose
Branden Jacobs Jenkins
“I would tell my younger self to hydrate. Wear sunscreen. Covid’s coming. Don’t lose your gym membership. Don’t be discouraged.
I was so lucky to get so much great advice from colleagues and mentors. I couldn’t have gotten here without that support. I would tell myself to listen to my friends.
At Purpose it really feels like a family backstage. It has been the true definition of an ensemble. Everyone is so supportive and caring.
There’s shockingly no drama. I’m so inspired by everyone involved. Writing was easy and a joy.”
Jasmine Amy Rogers, Outstanding Lead Performance in a Musical, BOOP! The Musical
Jasmine Amy Rogers
“I dreamt what it’s like to be a part of this community for so long, and I don’t think I dreamt it would be like this, at least so fast. I was just standing with Audra McDonald, Norm Lewis, and Brian Stokes Mitchell, and these are people that I looked up to and loved for so long. It’s really cool. Audra was telling me that my voice reminds her of one of her aunts who has passed. That was really special.
The advice I would give to my younger self would be to be yourself. The advice I give to other people is the advice I still give myself. Growing up I was a little weird, loud, and annoying sometimes, but I think I wouldn’t be here if I weren’t those things.
The line from BOOP! that epitomizes this experience is: ‘This day off is exactly what I hoped it would be. I feel alive again, maybe for the very first time.’”
Rick Sordelet and Christian Kelly-Sordelet, Outstanding Fight Choreography, Pirates! The Penzance Musical
Rick: “[Conceiver] Rupert Holmes gave us a sheet of music that had eight bars of fight. That’s what they did at the Public [in the ’80s]. There were eight bars of fight music. For this production, ours was six pages long. It was a big number. [Choreographer] Warren [Carlyle] and [director] Scott [Ellis] were amazing and so collaborative. Warren in particular had a lot of great insights on how the anatomy of the fight would be built. It was great to have him included as an architect to the fight work.
I’ve been very lucky and had a 40-year career. My first Broadway show was Beauty and the Beast, then The Lion King, and then Titanic. I had a lot of musicals. When my son Christian was 10 years old, I took him with me for I Hate Hamlet and said, ‘Okay, show me something that you’d like to do.’ He took a cell phone with an antenna, and we brought that into the sword fight. He was a natural. In college, he did hundreds of episodes of Guiding Light with me while he was in film school. We’ve had a great chance to work together a lot.”
Christian: “We also do a lot of work with opera and ballet, so doing a sword fight to music isn’t something that was unfamiliar.”
Rick: “We also did Chappell Roan’s performance at the VMAs when she did ‘Good Luck, Babe!’ We got to work with some amazing people and put this huge sword fight on stage. Sordelet Inc. is the only native owned, family run action company, and we get to work with really diverse people.”
Andrew Resnick and Michael Thurber, Outstanding Orchestrations, Just in Time
Michael: “When we created the sound for Just in Time, we honored what was initially developed and then determined what we wanted to keep and what would help further the story at any given moment. We also really wanted to make it sound present. Jonathan comes out as Jonathan Groff in 2025 at the top of the show. It’s not going to necessarily sound like a band in 1959 because we want it to sound modern as well.”
Andrew: “A lot of people didn’t know Bobby Darin’s music. We weren’t familiar with it either because nobody realized that all of these hits were the same guy! There’s so many different genres that he covered. That was sort of the playground for us because we got to do everything: folk music, big band music, early rock-and-roll music. His catalog is insane. That was the biggest challenge and also the most fun part as musicians.”
Michael: “All of us on the team used to joke that on paper we couldn’t have imagined that this would be as exciting as it was. [Director Alex Timbers] had an idea on how to make this something really special.”
Andrew: “Alex had a vision that this was going to take place in a night club. He knew how the stages were going to be set up; he knew where the band was going to be, and he knew how interactive the whole show was going to be. Alex is so skilled at really elevating the best parts of everyone and what they bring to the table and then putting them all on display. He has an amazing ear for orchestration and he would guide things. I’m very grateful to him for all of the things he’s done.”
The Drama Desk is composed of dedicated theater critics, journalists, editors, and publishers who cover plays and musicals throughout the season.