Darren Criss Is Betting Big on Maybe Happy Ending, the Musical You're About to Fall in Love With

Darren Criss has danced up the corporate ladder as J. Pierrepont Finch, stripped down to his skivvies as a queer East German rock star and tackled the “profane poetry” of David Mamet. And still, he says, there’s one thing he hasn’t done: “I haven’t taken any risks on Broadway.”

That ends this season with Maybe Happy Ending, a new musical on a mission to draw audiences to the Belasco Theatre without the benefit of a recognizable title, popular source material or songs that have already spent time on the Billboard Hot 100. “It's a really, really hard market right now to be making art,” Criss says to Broadway.com Editor-in-Chief Paul Wontorek, chatting at So & So's Neighborhood Piano Bar. And commercial Broadway theater? It’s “tedious, expensive and a gamble.” So naturally, Criss is going double or nothing as both star and producer of Broadway’s next thrilling crap shoot.

Maybe Happy Ending takes the trappings of a classic love story and inserts futuristic robots with outdated software. Criss plays Oliver opposite Helen J Shen’s Claire—a pair of Helper-Bots who, on a quest to contact their former owner, evoke a kind of Millennial-Gen Z mismatch. But rather than getting swept away by love, the two retired machines take the concept itself and try to break it down to its zeros and ones. As Criss explains, “[It’s] two computers trying to computationally synthesize and process what love is and why human beings do this.”

The musical was a hit when it debuted in Seoul, South Korea nearly a decade ago, and now, writers Will Aronson and Hue Park have a crafted an English-language version that Criss thinks has the potential to ascend to the proverbial Heaviside Layer of musical theater. “This is the seminal version that I hope can last in perpetuity for the ages,” he says, adding confidently, “I do feel like this is a timeless piece.”

Original musicals have the most challenging road on Broadway. But when you look to grassroots successes like Urinetown, or Dear Evan Hansen, or even The Prom—which ran in New York for less than a year but inspired a starry film and a slate of regional and international productions—you see how quickly an unknown quantity can become canon. “People are always like, ‘There’s no one creating original things,’” Criss says. “They are. It’s just really, really hard to produce them because you really have to believe in something hard enough to be OK with the risk.”

The fact that Maybe Happy Ending has earned that belief from some of the theater’s heaviest hitters is telling. Director Michael Arden, hot off a 2023 Tony Award for his revival of Parade, chose the piece as his next musical. And producers Jeffrey Richards and Hunter Arnold, with nearly 20 Tony Awards between them, have given Arden free rein to make a capital “B” Broadway meal of it.

The show’s cast is deceptively modest (Marcus Choi and Dez Duron complete the four-hander), but there’s nothing minimalist about Arden’s vision for Maybe Happy Ending or the high-tech space he’s worked out with set designer Dane Laffrey. In short, “They don’t f**k around,” says Criss. “This show is very technologically advanced. I think it's kind of the ace in the hole that people aren't expecting.” He tosses out comparisons to Miss Saigon’s descending helicopter and The Phantom of the Opera’s haunted chandelier—emblems of the bygone ‘80s megamusical. In an era of subtlety and economy (think recent Tony winners Kimberly Akimbo or The Band’s Visit), this, Criss promises, is “a big-a** mother**king spectacle.”

It's another bold, all-in move from the Maybe Happy Ending team, but Criss is determined to hedge no bets this time around. He looks back at his Broadway resume: How to Succeed in Business Without Really Trying (“Glee was white-hot and I was going in for three weeks after Daniel Radcliffe”); Hedwig and the Angry Inch (“People love that show. With or without me, it would be just fine”); American Buffalo (“A beloved and respected American play”).

“They're all classics to some degree,” he concludes. “This is not that.” Of course, understanding what Maybe Happy Ending is not is less of an issue than getting audiences to understand what it is. Right now, Criss says, there are rumblings around town that it’s “the cute little robot show.” The thought puts a mischievous grin on his face: “You have no idea.”