Maybe Happy Ending, fresh off its big win as Best Musical at the 2025 Tony Awards, rolled into NPR’s Tiny Desk studio for a special performance.
The musical centers on the story of two humanoid robots, Claire and Oliver, played by Helen J. Shen and Darren Criss, who find love and connection during a bittersweet road trip.
Created by Hue Park and Will Aronson, Maybe Happy Ending digs genuinely into questions of purpose, connection and what it means to live after your original purpose has ended.
Backed by a lively ten-piece orchestra, the Tiny Desk performance includes all four cast members sharing highlights from the show.
The memorable refrain of Where You Belong stands out as Criss’s Oliver imagines reuniting with his former owner James, brought to life by Marcus Choi.
There’s real chemistry between Shen and Criss, especially on the playful number The Rainy Day We Met, which lets us see just how well these two performers connect onstage.
Composer and lyricist team Park and Aronson introduce A Sentimental Person, performed by Dez Duron as Gil Brentley – a character who channels the classic coolness of Sinatra while voicing the deeper feelings Oliver struggles to express.
The set wraps up with the moving duet When You’re in Love from Criss and Shen, a finale that resonates just as powerfully in the intimate space of the Tiny Desk as it does on Broadway.
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