Stella Cole steps in as Gil Brentley in Maybe Happy Ending from October 20

Stella Cole at the piano. Photo by Laurel Hinton The jazz singer Stella Cole will make her Broadway debut on Tuesday, October 20, stepping into the role of Gil Brentley in Maybe Happy Ending at the Belasco Theatre for a four-week engagement while Dez Duron takes a short leave from the production.

Cole plays the part through Sunday, November 15, 2026, and Duron, an original member of the company, returns to the Belasco on Tuesday, November 17. Gil (pronounced “Jill”) is the jazz singer whose records keep the helper robot Oliver company, so the role goes, for a month, to a performer whose following was built on the standards rather than on theater credits.

Raised in Springfield, Illinois, Cole studied theater at Northwestern University before turning, during the pandemic, to singing videos she produced herself; that audience now stands at 1.7 million followers. Since moving to New York she has headlined at Café Carlyle, Birdland and Town Hall, played more than 100 headline dates across the U.S., Europe and Asia in 2025, and signed her first major-label deal, with Decca Records. She has since released two albums, It’s Magic and Stella Cole Live at Café Carlyle.

Ahead of her first performance the production has released a recording of Cole singing Why Love, Gil’s number, accompanied by the show’s co-writer Will Aronson.

The substitution falls in the musical’s second year at the Belasco, where it opened on November 12, 2024 and went on to win six Tony Awards, Best Musical among them. On Tuesday, July 7 it gave its 688th performance there, the longest run in the theater’s history, overtaking the 687 performances that Dead End logged in 1937.

The musical has book, music and lyrics by Aronson and Hue Park and is directed by Michael Arden. Set in Seoul in the near future, it follows two outdated helper robots whose chance meeting turns into something neither was built for.

Tickets are on sale through Sunday, February 28, 2027 at the Belasco Theatre box office, 111 West 44th Street, and through Telecharge. A limited number of in-person rush seats are sold at the box office each day it is open, from 10am (noon on Sundays), at $49 including fees; digital rush tickets cost $45 from 11am on the day of the performance, two per customer; and the “Club 2064” digital lottery offers pairs at $20.64 a ticket.