Making Music on Her Own Terms

Country music artist & Livano resident, Jesslee, talks about what drives her

Don’t try to put Jesslee into a box—she won’t fit. Unless it’s a really, really big box, big enough for all the different hats she wears as a country music singer-songwriter, big enough for the diverse elements she brings to the genre, big enough for the stories she has to tell, and big enough for her contagious laugh that can set the tone for a whole room. Add in the other ways she defies country stereotypes — including her Italian-American heritage and an impressive run as a competitive athlete — and it’s clear Jesslee defies easy categorization. That’s how she likes it. 

Though she cut her first EP in 2015 (while simultaneously working jobs at a bank and a Publix deli), many fans encountered Jesslee for the first time in 2018 when she appeared on NBC’s “The Voice.” She has opened for or performed with major names including Wynonna Judd, Thomas Rhett, Uncle Kracker, Dierks Bentley, and Cassadee Pope, and she charted for 45 weeks on Apple Music’s “Country Hot Tracks” in 2019 and 2020. Most recently, she signed with the label ONErpm in Nashville—another major milestone in her young career—and released the single “Unmeet You” along with the video, for which she wrote the storyline. 

That’s a fraction of the resume that establishes Jesslee’s credentials as an artist who’s earned her place on the stage. But it barely scratches the surface of Jesslee, the person. 

We let her share some of those highlights in her own words in a recent interview.

When people go to your site,, the first thing they see is the video for “Chillbilly.” It’s a great introduction, because it shows you know how to let your hair down and make room for fun and humor in your music—from the hook that’s still stuck in my head (“We just some front porch, back woods, head bobbin’ honky tonk hippies”) to the colorful characters in the video, including a woman walking downtown in a silk robe and curlers, a man wearing swim fins for no particular reason, and a goat in a tutu. What inspired that?

I wanted it to be campy, totally silly, fun, and feel good. When we wrote the song, it was literally me writing about my hometown of Stuart, Fla., where I moved when I was 14, and then we actually got to film there. The town has grown, but I wanted to create a picture of what it was then—so we filmed in historic downtown Stuart, included all my hometown best friends, and used these eccentric places where I grew up. Even though the production is really forward, it still fits in country music to me because it’s honest, raw, fun, and still simple in its own way. 

You’ve spent years successfully building an image and writing and releasing music on your own. What does it mean to you now to sign with a label? 

If it wasn’t for me having had that time of building and developing on my own, I would not have been able to sign the deal I have today, which is an extremely artist- and creator-friendly record deal. It’s pretty unheard of
today to have an artist who produces her own music, especially a female
artist, and especially an Italian-American in country music. I was able to build an audience who loved me for that beforehand and then find a label that wanted to plug into what I’m already doing.

It’s an exciting time at ONErpm. They’re doing something special, and this is a true equity partnership deal where I get to remain myself 100 percent.  

“Unmeet You” is another release that’s getting a lot of attention on social media. 

“Unmeet You” was a true story for me and one of the hardest songs to write, but it was also the song that really put me over the edge with the label signing me. When I was able to tell my story, I think the honesty really showed through, and they could feel it.

It’s about a guy I adored, and I found out he was cheating on me. I was so distraught. Time has gone on, and I have been with another person for five years now. I’m super happy. Still, I know there are people who are going through that right now or have gone through that, and they need that
reminder that it’s okay to hurt.

I want to ask about your athletic prowess, which is not something people usually associate with  being an artist. I understand you were a highly ranked tennis player when you were younger?

Actually, for the longest time, I didn’t think I was going to do music. While my sisters were doing musical theatre, I was an athlete. I started playing tennis when I was three. Tennis is an expensive sport and not really a thing in a po-dunk town. We were not well-to-do at all, but my mom figured out how to make it happen. She’s a superstar. She has always been there to make our dreams happen the best she could. So she let me start playing tennis, and I fell in love with it. I played until I was about 18. 

And then you switched to figure competitions? 

I had a bad breakup with a guy and gained a bunch of weight, and he told me I was never going to find anybody better than him. I was so motivated by that, because I wanted to prove him wrong. Pretty much immediately, I found my way into becoming a figure competitor in body building. My very first competition, I took the novice competition for first-time competing, and overall I took the whole show. That’s the Scorpio in me. I can’t stand when people tell other people their limitations. 

I think the artist I am and some of the music I release stems from being an athlete. I forever had a hashtag I would use, #musicandmuscles. You’d be surprised how well they coincide. I still go to the gym five times a week, and I’m always trying to push myself. It’s important to do something in your life where you’re consistently challenging yourself. It keeps you from becoming complacent with where you are. Complacency is a slow killer for your soul.

I watched the debut of “Songwriter Sessions” on YouTube, where you sit down and talk with your favorite co-writers and artists. What was your motivation behind that?

The series was inspired by my experience as someone who is a writer as well as an artist. I’ve written or co-written songs for other artists to record, and I’ve been slighted before. When you’re proud of something, you should be acknowledged for that as a creator and owner on the song. It’s important to me to showcase and support the writing community out here. Co-creation is such an important part of this industry.

Tell me about “Love Me Ugly,” which is another departure because it has such a great pop kick. 

It’s absolutely, extremely innovative pop-country music, for sure. I like to say that I’m country-centric, but sonically, I never want to be held back because I’m trying to fit into the box of “country music.” If I write something and love it and it’s grooving great a certain way when we start producing it, it doesn’t always make sense to have a big old banjo in it or a pedal steel. I’m not going to force that onto a song, just because.

That’s why I’ve kind of been known as a genre-bender in this town. Even though the majority of what I release is definitely country-centric, it’s going to push the limits. I grew up listening to Tanya and Merle and Waylon, and I love that music. But my vocal doesn’t necessarily suit traditional, simple, sweet country music. So when I produce things, I want to see if it’s going to be as powerful as my vocal, and let that shine. I want to trailblaze my own lane. There’s something exciting about mixing country music with different sounds and different cultures. It’s really a melting pot of music, and that’s what it always should be. It should be what America is, which is a melting pot of beautiful people.