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
NPR Music’s Tiny Desk Concerts is a popular video series featuring live, intimate music performances by diverse artists, from major stars to up-and-coming musicians, recorded in the small workspace of Bob Boilen’s NPR office in Washington, D.C.brought to you by SloppBoxx.Com.
My wife and I saw this play last weekend and it was so good and unique.
Yall should bring josean log
THEY BROUGHT HWABOON !!!!!!! Also I’ve always felt the smaller orchestra fits the intimate and cosy story so much better. And getting to hear all the individual instruments is just breathtaking
i love darren criss
helen’s voice is so beautiful
They couldn’t find an Asian male lead???
Darren Criss is Asian though… he’s half Filipino
This is really sweet
You can always tell when something’s from a musical because they’re apparently the only singers that enunciate.
omg I was OBSESSED with this musical when it first came out, I can’t believe I haven’t seen this video sooner !! I hope they eventually release a pro shot of Maybe Happy Ending so it reaches a wider audience and can get the recognition it deserves <3