Mitra I. Arthur | March 5, 2026 What can robots teach us about humanity and about love? Maybe Happy Ending, the 2025 Tony Award winner for best musical, tells the unlikely story of two humanoid robots, portrayed by Helen J. Shen (Claire) and Darren Criss (Oliver), as they fall in love while on a road trip. The show’s creators, Hue Park and Will Aronson, fill the musical with a sense of yearning, not specifically for romance (though that does happen), but for connection and self-actualization: Our heroes try to understand what it means to actually live once your purpose for existing is over.
Backed by a ten-person orchestra, the four cast members present selections from the show at the Tiny Desk. The repeated whimsical refrain of “Where You Belong” pulls us into Olivier’s imagined reunion with his former owner James, portrayed by Marcus Choi. The banter between Shen and Criss for “The Rainy Day We Met” is charming — and just a glimpse into how perfectly they play off each other.
Park and Aronson introduce “A Sentimental Person,” performed by Dez Duron who plays the suave, Sinatra-esq jazz crooner Gil Brentley. Brentley serves as a musical avatar for Criss’ “Oliver,” facilitating the complex emotions that Oliver is unable to articulate. They close the set with “When You’re in Love,” a tear jerker of a duet from Criss and Shen. And as the music swells, you’re right there with them in the moment: They don’t have to wait for an invitation to your heart; they, and this show, are there already.
SET LIST “Where You Belong” “The Rainy Day We Met” “A Sentimental Person” “When You’re in Love”
MUSICIANS Darren Criss: vocals Helen J. Shen: vocals Dez Duron: vocals Marcus Choi: vocals Will Aronson: emcee, writer Hue Park: emcee, writer John Yun: keys, conductor, music director Cenovia Cummins: violin Rachel Handman Robison: violin Orlando Wells: viola Jessica Wang: cello Conrad Korsch: bass Joshua Mark Samuels: drums, glockenspiel, malletKAT Rick Heckman: clarinet, alto sax, piccolo John Bailey: trumpet, flugelhorn Julie Dombroski-Jones: trombone
TINY DESK TEAM Producer: Mitra I. Arthur Director/Editor: Kara Frame Audio Director/Mix: Josh Newell Host/Series Producer: Bobby Carter Videographers: Kara Frame, Maia Stern, Joshua Bryant, Zayrha Rodriguez Audio Engineer: Tiffany Vero Castro Production Assistants: Dhanika Pineda, Alina Edwards Photographer: Michael Zamora Tiny Desk Team: Ashley Pointer, Felix Contreras Series Editor: Lars Gotrich Executive Producer: Suraya Mohamed Executive Director: Sonali Mehta Series Creators: Bob Boilen, Stephen Thompson, Robin Hilton
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