Pronounced Jill, Stella Cole Makes Her Broadway Debut at the Belasco

Stella Cole makes her Broadway debut on Tuesday, October 20, as the jazz singer Gil Brentley in Maybe Happy Ending at the Belasco Theatre, and she stays in the role through Sunday, November 15.

The name is spelled Gil and said Jill. Cole is the first woman to play the part on Broadway, according to New York Theatre Guide. She is keeping the seat warm for Dez Duron, an original cast member who is taking a short leave and comes back on Tuesday, November 17.

She is not the only new face in the building this week. Hannah Kevitt, who opened the show as Claire, played her last performance on Sunday, October 18. Savy Jackson, who had been Claire's standby, takes the role full time starting the same Tuesday as Cole, per Broadway.com. Two women walk into the Belasco company on one night.

Who Is Stella Cole?

Cole is a jazz vocalist who built her following online by singing old standards, then took that audience into New York's supper clubs. She has played Café Carlyle, Birdland and Town Hall, according to New York Theatre Guide, and Universal Music's announcements add Carnegie Hall and Madison Square Garden to the list.

She grew up in Springfield, Illinois, and went to Northwestern. In a September interview with John Bommarito of WEMU, she said she was a junior in college when the pandemic lockdowns began and sent her home to her parents. Her father pushed her to post videos of herself singing. She downloaded TikTok and did. One of her first captions, as she recalled it, read "LOL, I don't know what I'm doing. Hope my friends never see this."

Then came New York, and the slower work of being taken seriously in the city's jazz rooms. She told WEMU she walked dogs to pay the bills and practiced while she did it. She also told him she was not very good at the dog part.

"But I am a Midwest girl at heart."

Broadway.com notes she was named an Amazon Breakthrough Artist to Watch last year and has sung on The TODAY Show, Live with Kelly and Mark and Tamron Hall. She has toured with Scott Bradlee's Postmodern Jukebox, which she told WEMU was her first time on the road.

What Is Gil Brentley Doing in a Robot Musical?

Maybe Happy Ending is a musical about two obsolete humanoid robots in Seoul. Oliver is a retired helper robot who loves his jazz records. Claire, his neighbor down the hall, knocks to borrow his charger, and the two end up on a road trip across Korea.

The show won six Tony Awards in 2025, including Best Musical. Will Aronson wrote the music, Hue Park wrote the lyrics, and the two wrote the book together. Michael Arden, a Tony winner, directs. Zachary Noah Piser plays Oliver and Marcus Choi plays James.

The casting has a neat logic to it. Cole has spent her career on the Great American Songbook, the kind of classic standards a robot with a shelf of jazz records would know by heart. TheaterMania ran a clip of her singing "Why Love" with Aronson accompanying her when the news broke on October 1.

It is also the stage she wanted first. Her first role, she told WEMU, was a zebra in a first-grade community production of Children of Eden. "I wanted to be on Broadway," she said. "That was a dream originally."

What Else Is She Releasing This Fall?

A new album. Imagination is due Friday, October 30, ten days into her run, according to WEMU and Broadway.com. It is a set of Songbook classics recorded with her touring trio, Michael Kanan on piano, Michael Migliore on bass and Hank Allen-Barfield on drums. She told WEMU the songs were first meant to sit inside her last studio album, It's Magic, which came out in August 2025.

In between came Live at Café Carlyle, set by Decca Records US for release on June 26. Universal Music says it was recorded from June 17 to 21, 2025, during her sold-out debut residency there. She told WEMU she has now played the room twice.

So the fall has a shape. A Broadway debut on a Tuesday, a studio record ten days later, and the Belasco stage for four weeks in between.

What to Know Before You Go

Cole plays Gil Brentley from October 20 through November 15 only. Duron returns on November 17. Maybe Happy Ending runs 1 hour and 40 minutes with no intermission, and New York Theatre Guide recommends it for ages 8 and up, with no children under 4 admitted.

Broadway debuts keep arriving this fall. Margaret Cho takes the Narrator's chair in The Rocky Horror Show at Studio 54 on November 3, as we reported in The Next Narrator.

The robot puts on a record, and for four weeks the jazz singer in the room is a former dog walker from Springfield who sang her way here one video at a time.