SONGWRITER, GUITARIST, HUMAN: Jessy Esterline plays two shows this weekend at Edward Teach and Katy’s

“I think the magic of music is it speaks to everyone differently at different times in their lives,” singer-songwriter Jessy Esterline muses. “For me, it’s always been about connecting to that feeling in those moments and trying to replicate that internal feeling out loud.”

SELF-EXPRESSION  Jessy Esterline dives into covers and originals at her live shows. Courtesy photo
SELF-EXPRESSION: Jessy Esterline dives into covers and originals at her live shows. Courtesy photo

Esterline’s love of music started on the ivory keys early in life, then later with guitar. Always, music has been a form of her self-expression, whether via songwriting or in the covers she chooses to play, like Dolly Parton’s “Jolene” or “Bittersweet” by The Verve, even to Beyonce’s “Halo.” It’s all about organically connecting to her audience.

The musician made her way to ILM after her service with the U.S. Air Force. Esterline now performs among Wilmington’s supportive musicians, artists and business owners who open their doors to them. “I’m just happy to live in a place that is so welcoming to musicians and songwriters,” she notes. “The talent in the city is incredible.”

While Esterline recently has found new inspiration for songwriting, her most recent collection of tracks can be heard on Soundcloud or at one of two live shows this weekend. She will play on Friday, November 23, at Edward Teach Brewery and on Saturday, November 24, at Katy’s Grill and Bar. encore spoke with Esterline to get her story.

encore (e): Tell our readers more about yourself as a songwriter, guitarist and human.

Jessy Esterline (JE): I’ve always been a little socially awkward and a bit clumsy, so naturally I made a habit of playing expensive instruments and conversing with strangers about it. In all seriousness, I learned to play guitar because it was easier to tote around than a piano (my first love). I’ve learned not to drop things as much as I used to. I think the familiar struggle with any form of self-expression is learning to become comfortable with vulnerability. I’m still learning how to become more vulnerable in my writing and in sharing that with an audience. So, when I can marry those two things, it’s a great feeling. I moved to Wilmington in 2017 to expand upon some professional opportunities and to be closer to my family. It’s a city that has always had a certain charm and now I get to call it home.

e: How long were you in the Air Force and what did you do?

JE: I served for four years as an Aircrew Flight Equipment Technician, fixing and maintaining all emergency, and survival gear that aircrew members use, such as parachutes, night-vision goggles, slides and rafts for the airplanes, chemical warfare equipment/attire, etc.

e: You explore ideas around faith and life changes in songs like “Elm”—tell us about the song’s origins and more about what this is about.

JE: “Elm” is probably one of my most personal songs and one of the first songs I ever wrote. I was a caregiver for my grandmother who had Alzheimer’s, so as I was writing it I was in a state of double-grief, juggling life’s responsibilities, and trying to make sense of such terrible disease. It was a way of coping and honoring those moments with her; however painful they were. I named the song “Elm,” for her initials and it just so happened to be the name of the street I lived on at that time.

e: How did you connect with violinist Grace Haskin we hear on this song?

JE: Grace Haskin is my very best friend and oftentimes, my muse. She played a huge role in helping me cope during that extremely hard time in my life through music and friendship. I’m honored to know and love her, but I’m also incredibly amazed by her musicianship and talent.

e: “Tell It Like It Is” has more bass, piano and a jazzy storytelling vibe …

JL: That was one of those [exploratory] songs. To be honest, It started as a little improv in Garageband, but I ended up liking the vibe enough to share it. Funny enough, some folks liked it, so I kept it around.

e: Tell us about what you’re working on these days and if there are relatively new songs folks will hear at the shows at Edward Teach and Katy’s?

JE: I was in a writer’s lull for a bit, but I feel like I’m finally starting to revamp my writing lately. While I enjoy players covers I’ve had my eye on a few keyboards, just kind of flirting with the idea of bringing that into play during a live show soon and switch things up a little. I love playing covers (requested from the patrons at the venues), but I’ve also been shaking the dust off of some of my originals, so it’ll be really nice to play those out at these upcoming shows and see how that resonates with folks.

e: What are some other originals you’d like our readers to know about?

JE: “This Little Dream” is probably my favorite original song. I’m kind of a hopeless romantic, so I wrote it to my future “person”.  A few years later, my “person” finally came along, she said yes, and now we are planning our wedding. My little dream is now a huge reality and I couldn’t be happier. Every time I play it now I feel like I need to get pinched because she’s more than I ever dreamed of. Gush, gush, gush.

e: Any new covers you’re exploring these days that we’ll hear next weekend? What’s your “twist” on them?

JE: I’m all over the place, but lately I’ve been on a really big roots-rock kick. So, I’m trying to do more current covers of singer-songwriters in that space.

Jessy Esterline
Fri., November 23, 8 p.m. • Free
Edward Teach Brewing
604 N. 4th St.
Sat., November 24, 9 p.m.• Free
Katy’s Grill And Bar
1054 S. College Rd.

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