Maybe Happy Ending: Tiny Desk Concert

Maybe Happy Ending: Tiny Desk Concert with tags npr, npr music, national public radio, live, performance, tiny desk, tiny desk concert, tony desk, tiny concert

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

#tinydesk #nprmusic #maybehappyending

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