Stella Cole makes her Broadway debut as Gil Brentley in “Maybe Happy Ending”

Broadway welcomes a new star from the internet: Stella Cole, the 27-year-old jazz singer who became famous singing the great American standards on TikTok, will take to the Broadway stage for the first time as Gil Brentley in the Tony-winning musical “Maybe Happy Ending”. As Playbill reports, Cole will be the first female performer of this role in the production’s history — during her engagement, the name will be pronounced “Jill”. The limited four-week engagement starts on October 20 and runs until November 15 at the Belasco Theatre.

Cole takes the place of Dez Duron, the original cast member, who is taking a short break and is expected to return to the company on November 17. Playbill has also published an exclusive video clip in which the singer performs the musical’s song “Why Love?”, accompanied by Tony-winning composer Will Aronson himself.

Cole’s road to Broadway began on TikTok during the pandemic, when a clip of her singing “Over the Rainbow” went viral and brought her tens of millions of views; today she has over 1.7 million followers on social media. The Springfield, Illinois native, inspired by Judy Garland and Barbra Streisand, has since performed at prestigious venues such as Birdland, Café Carlyle, Carnegie Hall and Madison Square Garden, has toured with Postmodern Jukebox and released her debut album in 2023, followed by “It’s Magic” with Decca Records in 2025.

“Maybe Happy Ending”, with book and music by Hue Park and Will Aronson, opened at the Belasco Theatre on November 12, 2024 and was named the most acclaimed production of the 2024–2025 season, with 10 nominations and more Tony Awards than any other show. The story follows Oliver and Claire, two helper robots considered obsolete in Seoul, South Korea, who form an unexpected bond. It is directed by two-time Tony winner Michael Arden, while the current cast is led by Zachary Noah Piser as Oliver and Hannah Kevitt as Claire.