Stella Cole to join 'Maybe Happy Ending' Broadway cast

The acclaimed jazz singer will play a limited four-week run as Gil Brentley, becoming the first woman to perform the role in the Tony Award-winning musical.

Summary

• Jazz singer Stella Cole will star as Gil Brentley in Maybe Happy Ending on Broadway from October 20 to November 15
• She temporarily replaces Dez Duron and becomes the first woman to play the role on Broadway
• The show follows an unlikely romance between two obsolete robots
• The show won the 2025 Tony Award for Best Musical

Sing it! Musician Stella Cole will join the cast of Maybe Happy Ending on Broadway this fall, performing at the Belasco Theatre from October 20 to November 15 only. She will become the first woman to play the role of jazz singer Gil Brentley (pronounced "Jill") while original cast member Dez Duron takes a short leave from the production, returning November 17.

Cole makes her Broadway debut after rising to fame on social media for her renditions of jazz standards. She has been named an Amazon Breakthrough Artist to Watch and has performed at renowned NYC jazz venues like Cafe Carlyle, Birdland, and Town Hall.

Maybe Happy Ending follows two obsolete, humanoid robots who develop an unexpected connection on a road trip across Korea, and it won six 2025 Tony Awards including Best Musical.

Alongside Duron, the current Maybe Happy Ending cast includes Zachary Noah Piser as Oliver, Hannah Kevitt as Claire, and Marcus Choi as James and others. Tony Award winner Michael Arden (The Lost Boys, Parade) directs.

Get Maybe Happy Ending tickets now.

Photo credit: Stella Cole. (Photo by Laurel Hinton)