Maybe Happy Ending and Purpose Have Won a Lot of Awards. But Will They Win Tonys?

The Drama Desk Awards were announced on Sunday June 1. They are traditionally the last major theater awards presented before the Tony Awards, which will be broadcast live on Pluto TV and CBS this coming Sunday, June 8.

The Broadway musical Maybe Happy Ending took home the most awards of the night, including Outstanding Musical. This month, it also won the Outer Critics Circle Award for Outstanding New Broadway Musical and the New York Drama Critics’ Circle Award for Best Musical. That looks like real momentum for the little musical about Korean robots in love, but does that mean it’s guaranteed to win the Tony Award for Best Musical on Sunday?

Maybe not. Its biggest competition for the Best Musical Tony is Dead Outlaw, the macabre tale of Elmer McCurdy, whose corpse was displayed as part of sideshows and film promotions for the better part of the 20^th century. That show won the Drama Desk for Outstanding Musical last year when it debuted off-Broadway with Audible. In also won the 2024 New York Drama Critics’ Circle Award for Best Musical and the Outer Critics Circle Award for Outstanding New Off-Broadway Musical.

Because these three awards organizations consider off-Broadway as well as Broadway, Dead Outlaw was laureled for its off-Broadway debut last year and was not considered this year for its Broadway run, which has retained its original cast and creative team. In some ways, that has cleared the way for Maybe Happy Ending, which is still heavily favored to win a slew of Tonys on Sunday, including Best Musical, but which will have to overcome last season’s off-Broadway favorite to snatch the crown.

A similar story is unfolding in the Best Play category. Branden Jacobs-Jenkins, who won the Revival of a Play category last year for Appropriate, is back this season with a brand-new family drama, Purpose. It won this year’s Pulitzer Prize, the New York Drama Critics’ Circle Award, and Drama Desk Award for Best Play. That would seem to put it on a path to win the Tony Award for Best Play were it not for one little hurdle with bratty curls.

That’s Cole Escola’s riotous comedy Oh, Mary!, which has played to sold-out houses since it opened on Broadway last July. It also got its start off-Broadway last season, winning Escola the OCC’s John Gassner Award and the Drama Desk’s Sam Norkin Award (both awards are for early career artists, and while Escola has been a fixture on the downtown cabaret scene for over a decade, Oh, Mary! represents their professional playwrighting debut). Arguably, Oh, Mary! is the biggest surprise of the season, and as I’ve already written, the Tony voters may want to reward that.

The steady stream of shows making the leap from off-Broadway to Broadway in the following season isn’t the only factor undermining the predictive power of other theater awards when it comes to this year’s Tonys. In 2023, the Drama Desk decided to go gender-neutral in its acting categories, placing male and female nominees in competition. At the time, there was some concern that this would result in categories dominated by one gender (men, it was most feared). To mitigate that possibility, the categories were expanded to 12 nominees, with two winners selected by the voters.

The OCC also went gender-neutral that year but kept its categories to 5-6 nominees. Unlike the Drama Desk, the OCC has separate categories for Broadway and off-Broadway performers (a change that was made in conjunction with going gender-neutral) so the same number of awards are presented each year—but more of them are guaranteed to go to off-Broadway performers.

Two years later, we have some idea of how this gesture toward equity is working. Of the 12 nominees for the Drama Desk for Outstanding Lead Performance in a Play, six are women and six are men. However, the two winners are both women and both happen to be the front-runners in the corresponding Tony category: Sarah Snook (The Picture of Dorian Gray) and Laura Donnelly (The Hills of California).

Something similar played out in the Outstanding Lead in a Musical category. Seven of the 12 nominees were women, and the two winners were Jasmine Amy Rogers (Boop!) and Audra McDonald (Gypsy)—again, the two front-runners in the Tony category.

Two women—Amelia Yoo (John Proctor Is the Villain) and Kara Young (Purpose)—also won the Featured Performance in a Play category, which had eight female nominees and four male nominees. A pattern seems to be emerging: not that Drama Desk voters will support only men in gender-neutral categories, but that they will use gender neutrality as an opportunity to give more trophies to fabulous ladies.

Of course, the Featured Performance in a Musical category complicates that narrative. Eight of the 12 nominees were men and, due to a tie in the voting, three of them won Drama Desk Awards: Michael Urie (Once Upon a Mattress), Brooks Ashmanskas (Smash), and Jak Malone (Operation Mincemeat). But again, the latter two are the front-runners in their category at the Tonys.

While it’s not yet clear what sexless acting categories mean for gender equality, it seems quite apparent that having two winners in each category is allowing the Drama Desk voters to, in some case, opt out of a difficult choice and give the award to the two best performances of the year, regardless of gender—to give it to both Audra and Jasmine. It’s a lovely bit of kumbaya (not for Jonathan Groff and Darren Criss), but it makes the Drama Desks much less useful as a predictor of what will happen at the fusty old Tony Awards, which still divide performers into “actors” and “actresses.”

And what of the Outer Critics? They also gave awards to both Laura Donnelly and Sarah Snook, although the latter won in the Solo Performance category and was not in direct competition with the former. Jasmine beat Audra (and Darren Criss) in the Lead Performer in a Broadway Musical category. And Jak Malone beat Michael Urie and Danny Burstein in a Featured Performance category that did not include Brooks Ashmanskas as a nominee.

All that is to say, take the award wins of the past month with a grain of salt. There’s still room for surprises on Sunday night.