“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.”

In this interview spotlight, I chat with Baileigh Jane about AI in music, dream collabs, the latest release, and more.

Full Q&A along with links and music below.

Let’s get this hot topic out of the way from the start. What are your feelings on AI as a creative tool? Have you experimented with it? Or released any projects where it was used?

I don’t use AI, especially when it comes to music. Making the music is actually the fun part! I don’t think AI is very sustainable: economically, environmentally, or creatively. I’m not scared of AI either. Because it only shines a brighter light on how being a musical artist is about so much more than the music we put out, but about what aspects of our humanity we can champion.  

What is your earliest music memory? Or a moment that sticks out for motivating you to write, record, and release music?

I remember counting the verses and choruses in an Eminem song trying to understand song structure when I was 4 years old. At 5, my grandmother passed away and I wrote my first song about her. It was called “Granny’s Smile”. The song was meant to be healing for me and my mom, who I shared it with. There was something in me even then that realized songs can transcend difficult conversations. 

What’s up with this latest release? Any cool back-stories, bloopers, or notable inspirations?

The inspiration behind my latest release, ‘Biggest Regret’, was the growth I’ve had over the last 5 years since cutting contact with my mom, moving to NYC and coming out as transmasc nonbinary. I was excited to share this queer anthem which can touch on some of our mutual struggles while embracing a lush and groovy feel.  

What keeps you going, especially on the “bad” days?

Coffee, weed and music keep me going on the daily. But my worst days? I’ll need the extra time with my family and friends, especially my wife and our pets!

If you could collaborate with anyone – dead or alive, famous or unknown – who would it be and why? 

Kim Petras! I wasn’t necessarily a slut pop girly. But after listening to her Problematique album, and a lot of her recent releases, I can say I love so many of her pop hooks. She’s an incredibly catchy and prolific songwriter! Plus, she’s a trans icon of course.

I know it’s hard…but favorite song (or artist) of all time? Or Top 3 if you can’t choose one…? 

All time? Sheeesh! No, I’d have to say right now– Kim Petras, New Jeans, Victoria Monet

Where’s the best place to connect with You?

Tiktok, IG, Youtube or my website!

I appreciate your time. Any last thoughts before signing off? 

Thank you for YOUR time 🙂 I have 4 more songs I’m releasing this summer, and hosts monthly events for the queer community in Brooklyn!