EXCLUSIVE PREMIERE: Baileigh Jane Unveils Powerful New Song “Biggest Regret”
“Biggest Regret,” Baileigh Jane is a song about loss—but more importantly, about self-definition, growth, and the freedom that comes with both. Rooted in bedroom pop textures—light snares, easy guitar grooves, and an intimate vocal delivery—the track balances a laid-back sonic palette with striking emotional weight.
“I wrote ‘Biggest Regret’ as my trans coming out letter to my mom who I haven’t spoken to in five years,” says Baileigh Jane. “The song is about navigating conflicting feelings around empowerment and grief: empowerment through being your most authentic self, and the grief that comes when you realize not everyone is meant to grow with you. This song was originally a ballad, until I produced it as a pop track because the more I sat with it the more I felt it as a queer anthem.”
Baileigh Jane is a Brooklyn-based, transmasc nonbinary singer-songwriter, multi-instrumentalist, and self-producing artist originally from Jacksonville, Florida. Self-taught since the age of five, Baileigh blends genre-fluid influences—ranging from Khruangbin and NewJeans to Blood Orange and Prince—into soulful, dreamy songs that sit between folk, pop, and alternative R&B. Known for soulful, dreamy, pop-infused songwriting, the Brooklyn-based artist previously drew attention with tracks like “Nonissue” and “Follow” from their self-produced EP Transitions, earning coverage from V13, Indiefferential, and Pario Mag.
After coming out publicly and recommitting to their artistic identity, Baileigh began revisiting and completing years of unreleased demos, weaving themes of gender, transformation, and self-trust into their work. Their music is deeply personal yet expansive, shaped by a DIY ethos and selective collaborations with engineers including Brok Mende (Friends of Friends Recording) and James Littier (HMNI Productions). As Baileigh Jane brings their coastal twang to Brooklyn, their mission remains unchanged: to connect those who feel forgotten with the deepest parts of themselves—even when the path there moves through grief.
Beyond their solo work, Baileigh is the founder of Conduit Media, a queer music collective and label through which they host and curate queer music showcases across NYC. With a growing focus on collaboration and production, Baileigh continues to build community-centered spaces for emerging artists while expanding their craft both onstage and behind the boards.
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