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“Following Your Heart Is a Zero-Loss Game”: Darren Criss Is Forging His Own Legacy

AMI coat, top, and trousers. Photographed by Kevin Sinclair for the June 2025 Issue of Vogue Philippines

Darren Criss is no stranger to the spotlight. But, does his latest role in Broadway’s Maybe Happy Ending solidify his place within the ranks of Filipino theater legends? 

Oliver, the main character in the Broadway musical Maybe Happy Ending, would be confused by the actor who plays him.

See, Oliver is a robot dubbed “helper bot” with a classic Type A personality: rigid in his ways and painfully calculated. He exists in Seoul in the distant future, where these bots are essentially humanoid versions of our current cell phones. Oliver has only one mission in life, which is to reunite with his human who left him in an apartment complex where other thrown-out bots reside. (Think of how your old blackberries are stashed away in some random cabinet drawer.) His only friend is a plant named HwaBoon who, audiences come to learn, is the most important character in the show.

The actor who brings this robot to life is Darren Criss who is anything but one-track-minded. The Filipino-American’s personal curiosity and dynamic career tell this best. Was it Glee where you first got to know his dark locks and melodic voice? Or, did you first see him hit the stage on Broadway in How to Succeed in Business Without Trying (2012)? Perhaps it was his role in Ryan Murphy’s Gianni Versace: American Crime Story (2018). His portrayal as Andrew Cunanan, the killer of the late fashion designer, earned him an Emmy, Golden Globe, and SAG award and placed him as one the few actors to earn the trifecta. Unlike Criss, Oliver has only had one job during his entire battery life. 

Darren Criss for vogue philippines white suit
TOM FORD shirt, jacket, trousers, and shoes. Photographed by Kevin Sinclair for the June 2025 Issue of Vogue Philippines

Yet, Criss breathes life into his mechanical character on stage as if he knows what it’s like to operate like a robot. But, perhaps he does. Perhaps, we, including those who have continuously waved a finger to AI and ChatGPT; all do. 

“Think of Aesop fables or Greek Mythology,” he tells Vogue. “These tales all displaced the human experience by using non-human things. We learn lessons about our own behaviors through animals, spirits, gods, or other totems because it doesn’t feel patronizing if we use human characters. I think using robots was an excellent metaphor for human life itself and the way we perceive the world; operating systems, battery life, logical programming versus illogical emotional responses. A lot of these human things lend themselves really well to computers and robots.” 

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PRADA shirt, sweater, and trousers. Photographed by Kevin Sinclair for the June 2025 Issue of Vogue Philippines
darren criss vogue philippines pattern top dancing
VERSACE cardigan and trousers, TOD’s belt, FLORSHEIM shoes. Photographed by Kevin Sinclair for the June 2025 Issue of Vogue Philippines

The last time Criss performed at the Belasco Theater where Maybe Happy Ending is showing until January 2026 was 10 years ago. At the time, he starred as Hedwig in John Cameron Mitchell’s Hedwig and The Angry Inch. “I love the poetry of my return to the Belasco theater a decade later,” he says. The aforementioned show is considered a classic in modern musical theater. It first debuted Off-Broadway in 1998, and later revived in 2014 starring Neil Patrick Harris. 

Then, he was continuing a legacy, but with Maybe Happy Ending, an original production directed by Tony Award Winner Michael Arden, written by Will Aronson and Hue Park, and produced by Jeffrey Richards, he’s forging his own. 

“As a creative person, you dream to be a part of something original and singular to itself. You can’t put lightning in the bottle, but you work hard until one day the serendipities fall into your lap. That’s what happened here; a new dream was achieved.” 

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There’s also another difference in his return to this theater. Unlike his previous solo-performance, he gets to share the stage in Maybe Happy Ending with his 24-year-old co-star Helen J. Shen graduated from the University of Michigan; the same school Criss graduated from in 2009. “I’m literally the upperclassman on stage,” Darren jokes. Shen plays a fellow thrown-out helper bot named Claire, who ends up bringing the spontaneity out of Oliver. 

“As a creative person, you dream to be a part of something original and singular to itself. You can’t put lightning in the bottle, but you work hard until one day the serendipities fall into your lap.”

But, with newness comes risk. Those in the artistic universe know that participating in original productions bears a certain weight on one’s shoulders; tenfold when you’re riding high from a previously successful project. Will it be successful? Will it resonate with the audience? How will it affect one’s reputation? 

Maybe Happy Ending may be a completely new production on Broadway, but it ultimately asks an age-old question: Is it better to have loved and lost than never to have loved at all? “There are prerequisites to every good story,” Criss says. “Themes of love, loss, life. Think of any Shakespearean play you’ve seen. These are universal macro-themes that are packed very neatly and effectively in the show.” 

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GUCCI top, trousers, and belt. Photographed by Kevin Sinclair for the June 2025 Issue of Vogue Philippines
RALPH LAUREN coat, shirt, and trousers. Photographed by Kevin Sinclair for the June 2025 Issue of Vogue Philippines

Speaking of universal themes, Oliver’s plant HwaBoon is perhaps the true star of the show. In fact, the last moments of the play zero-in on the plant before the curtains fall. “He’s a glorious symbol of love that can outlive time itself,” Criss says. When asked if he has a real-life HwaBoon of his own, he directs his answer to music. “As a musician, I have instruments whose sentimental value completely eclipses their actual effectiveness. My guitars, for example, have been there for many beautiful moments in my life.”

For Criss, success as an artist isn’t measured by how many tickets sell. “Following your heart is a zero-loss game. I had a strong feeling about the piece even before we opened the show. Whether or not people actually caught on was up in the air, but I would’ve still been very happy either way. On an artistic level, I was so moved that even if it didn’t reach the height that it is at now, I would’ve talked about it very proudly 20 or even 30 years down the line.” 

darren criss vogue philippines june 2025
GUCCI coat, shirt, trousers, and belt. Photographed by Kevin Sinclair for the June 2025 Issue of Vogue Philippines

The show has been running since November 2024 with ticket sales currently grossing $20,889,683. But, the Tony nominations speak for themselves. A day after Criss offered this humble note of measuring success to Vogue, news broke that Maybe Happy Ending was nominated for 10 awards for the 78th annual Tonys. The categories include: Best Musical, Best Original Score, and Best Scenic Design. Darren Criss is nominated for Best Actor. 

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When Filipinos think of stars on Broadway who share their ethnic backgrounds, Lea Salonga quickly comes to mind. She is, after all, the first Asian woman to win a Tony award. There’s also Eva Noblezada who held roles in Miss Saigon and Hadestown; and Rachel Ann Go who had roles in Les Miserables and Hamilton. Darren Criss, whose mother hails from Cebu and has an affinity for Palawan, puts in a case for his right to join their ranks as legendary performers. 

“I certainly don’t think of myself in that way,” he tells Vogue. “But, I think it’s my responsibility to rise to that occasion if that’s what people see me as. I especially look up to Lea Salonga in a revered way. I look at her as a beacon, but I wonder if she even sees herself in that way. See, it’s this sort of call to duty. Beacons give cause to our belief, and they make us feel like it’s worthwhile to believe in something. I am honored and privileged to be given that role if it’s given to me.”  

Vogue Philippines: June 2025

₱595.00

By ISIAH MAGSINO. Photographs by KEVIN SINCLAIR. Styling by DAVIAN LAIN. Editor DANYL GENECIRAN. Talent: Darren Criss. Grooming: Edward Cruz at Tomlinson Management Group. Executive Producer: Cherrelle Swain at Terra Rossa. Production Coordinator: Yahnnica Tate. Casting Director: DaVian Lain. Fashion Assistants: Genile Thomas, Chelsea Avila. Photo Assistant: Anna Istomina. Grooming Assistant: Michael Livsey. Darren Criss’ Assistant: Andrew Lewis. Retoucher: George Garfio. Special thanks to Michael Samonte at The Samonte Group.

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