A Surprise Win for The Prom and Other Things You Missed at the Drama Desk Awards

It looked like Tootsie would sashay to a big victory at Sunday's Drama Desk Awards. It started with David Yazbek's win in the Outstanding Music category. Trophy collected, the composer strutted offstage only to dance right back on a minute later when his name was announced for Outstanding Lyrics. He was quickly followed by his writing partner, Robert Horn, who won the Outstanding Book category for his hilarious script. Later in the evening Tootsie star Santino Fontana won for Outstanding Performance by a Lead Actor in a Musical. These exciting four wins, however, were not joined by an Outstanding Musical trophy — the top award given by the Drama Desk.

For the first time in years, the Drama Desk Awards ceremony was not live-streamed, so those following along at home were left with the vagaries of social media to convey just what an upset this was. But I was in the room when Joel Grey announced the top award, and it felt like a shockwave passed over the audience when he uttered the winner: The Prom.

This Story of the Week will discuss that surprise development, other Drama Desk reveals, and what it all means for the Tony Awards on Sunday. Could The Prom repeat its showing at the Drama Desk Awards and come from behind and win the Tony for Best Musical?

What did I miss at the Drama Desk Awards?
Beyond the aforementioned Tootsie roll, the Desk doled out much love to Hadestown, despite the show being ineligible for music, lyrics, book, and musical (all of which were considered in 2017 for the New York Theatre Workshop production). Hadestown won Outstanding Director (Rachel Chavkin), Outstanding Lighting Design (Bradley King), and Outstanding Sound Design (Nevin Steinberg and Jessica Paz).

André De Shields (who was not in the off-Broadway production) won Outstanding Featured Actor in a Musical, a feat he is almost certain to repeat at the Tonys. De Shields wryly remarked that it "only took six nominations" for him to finally win a Drama Desk before recognizing the work of his costar Patrick Page, who is nominated against him at the Tonys and according to our critics, represents his only real competition. Considering how well Hadestown did despite being barred from a lot of the categories, it appears to be in a good position heading into the Tonys.

As expected, The Ferryman beat out What the Constitution Means to Me for Outstanding Play, while off-Broadway's new Yiddish Fiddler on the Roof beat Oklahoma! for Outstanding Revival (as it did at the Outer Critics Circle Awards). On Sunday, Oklahoma! faces only Kiss Me, Kate, meaning it could finally get the award it deserves.

Elaine May won Outstanding Actress in a Play for her uncomfortably realistic performance in The Waverly Gallery. The famously reclusive actor-director was not on hand to accept the award, but word on the street is that she'll be there for the Tonys, where she's a lock to win. Accepting the Drama Desk on her behalf, presenter Bertie Carvel quipped, "There have been a lot of people played off by the band tonight, and I was really hoping Elaine May would break into song when they tried it on her."

How are the Deskies different from the Tonys?
While the Tonys consider only the Broadway season (37 shows this year), the Drama Desk considers the entire breadth of professional theater in New York. This year, that meant that the nominators (full disclosure: I'm one of them) saw 260 shows. Actors in off-off-Broadway shows (like Midori Francis of Usual Girls) are nominated against Broadway's A-list stars (like Elaine May). Seeing all of those people in the same room is the closest thing to a general assembly of the New York theater community.

One of the best shows of this season was the sci-fi folk musical Rags Parkland Sings the Songs of the Future: It was nominated for nine Drama Desk Awards and won none of them, which doesn't speak to the show's quality as much as its obscurity. My initial tickets to Rags were canceled when a fire sprinkler caused water damage to the set, leading Ars Nova to postpone press performances. It seems likely that many Drama Desk voters didn't reschedule — if they were even booked to see it at all.

The truth is that not all of the Drama Desk's voters see everything that has been nominated, and that is no one's fault in particular. The logistics of accommodating 108 additional voters (on top of the Drama Desk's two presidents and seven nominators) are daunting for a theater like Ars Nova that only seats 99. Most smaller houses invite just the nominators. While some Drama Desk voters make a point to keep up with the nominators, many don't in respect to their own personal limits (it really is a giant time commitment). So the shows that the most people saw (which are always on Broadway) inevitably win the final vote.

The Tonys don't really have this problem. It is perfectly manageable to see 37 shows in a year (only 25 of which were nominated), and it is also reasonable for big Broadway houses to accommodate 831 voters and their plus-ones. Additionally, a new digital voting system bars Tony voters from voting in categories in which they have not seen every nominee, with each voter submitting the date of the performance they attended each show before the ballot appears onscreen. Obviously, voters could lie about this, but they would have to make up a date of attendance that could easily be disproven by checking box office records — so who would do that? When it comes to voting, the Tony nominees are on far more equal footing.

Could The Prom really win the Tony for Best Musical?
It could! (But I still think it's unlikely.) Hadestown is the show to beat, and I suspect that voters will favor its eclectic score, modern spin on mythology, and compact production (which makes it ideal for touring). Still, The Prom has emerged as the underdog of this Tonys race, and it would make a Cinderella story for the ages if it were to win on Sunday — and if Tony voters love anything, it's a good story.

There was one thing that happened at the Drama Desk Awards that offered a hint as to why The Prom might triumph: While accepting the award, lead producer Dori Berinstein mentioned that The Prom was an entirely original musical, eliciting a loud and unexpected cheer from the audience. Of all the Tony nominees for Best Musical this year, The Prom is the only one not based on a pre-existing property (yes, the myth of Orpheus and Eurydice counts). This is an incredibly rare thing in musical theater (both Oklahoma! and My Fair Lady are adaptations of earlier works) because it is really difficult to pull off. And yet The Prom introduces us to a new story with new characters singing new songs, winning our hearts in just two hours, 30 minutes. That might just be enough to convince voters to crown The Prom Queen of Broadway.