Jenna Deweese: From the Classroom to the Stage, Teaching and Singing with Heart

For Jenna Deweese, music has always been more than just a pastime, it’s a calling. Whether she’s leading a room full of energetic elementary school students or standing under stage lights in front of a crowd, Jenna brings the same heart, joy, and authenticity to everything she does. As both a country singer-songwriter and a music teacher in Woodward, Oklahoma, Jenna is quietly building something special by sharing her voice, her stories, and her songs with anyone willing to listen.

Jenna’s journey into music began early, with one pivotal moment still standing out in her memory. “I wrote my first song at the age of eight in church,” she says. “I sang it in front of everyone, and I still remember how the crowd responded.”

Pictured: Younger Jenna on stage.

A significant influence came from a woman who saw her potential early on, her elementary school music teacher, Mrs. Sikes. “She gave me solos and recognized my talent,” Jenna recalls. That experience not only ignited her love of performing, but shaped her desire to give back. Today, as a music teacher herself, she hopes to be that same spark for the next generation. Instead of relying on pre-made classroom songs she didn’t connect with, Jenna began writing her own simple, playful tunes about colors, the days of the week, and even a name game that her students happily echo back each morning. Most of them don’t even realize their teacher is the one who wrote the songs they sing.

Her students may not realize the depth of the music they're singing, but the creativity and passion Jenna brings to her classroom spills effortlessly into her life on stage. “Kids are brutally honest,” she laughs. “But if I can be silly and fun in front of kids all day, I can absolutely handle being on stage for an hour or so.” That stage confidence has led her to play shows around the region, including a standout performance at The Doghouse in Tishomingo, Oklahoma, where she opened for Blake Shelton’s son, Zuma Rossdale.

“I really love playing The Doghouse,” she says. “I got to open for Blake Shelton’s son there, which was an incredible experience. I even ended up signing autographs while waiting in line for his. I felt bad at first, but it just kind of happened.” She laughs, still in awe.

Photo by Queen Bee Photography.

It was the kind of surreal, full-circle moment that reminded her of the first time someone asked for her autograph. An older gentleman approached her after a much earlier show at the same establishment  and told her, “I wanted to be the first one to get an autograph. I can’t wait to see you on TV.”

Jenna’s music has been described as country rooted in tradition, but with unmistakable female energy. “People have compared my range to Reba, and I’d say my sound is similar to old country, with a new twist,” she explains. Influenced by artists like Reba and Shania Twain, Jenna’s songs center around storytelling and emotional connection.

One of her originals, “Wild One,” is particularly close to her heart. “It’s about me stepping into my own creative self,” she says. “I was told my whole life that I had to fit into a box, but now I’m learning to let go of that. It’s a story about freedom, expression, and growth.”

Jenna usually writes alone, recording melodies into her phone as they come to her and building on them later in the peace of her music room. Currently, she’s working on two songs, one upbeat and one more somber. Each reflects a different side of her voice and her spirit. She’s also growing more confident in sharing her original material during live shows, thanks in part to her biggest supporter, her husband. “At first I was hesitant,” she says. “But my husband told me, ‘Those people out there probably haven’t written any music, so who are they to judge?’ And he was right.”

Photo by Queen Bee Photography.

While the road hasn’t always been easy, Jenna’s passion and drive shine through in everything she does. From teaching young students to inspiring audiences with her songs. “I hope people walk away from my performances feeling good and inspired,” she says. “Music is powerful like that.”

Though she may joke about needing sheet music or a tablet due to having suffered six concussions, it’s clear that Jenna’s gift lies far beyond what’s visible. It’s in her resilience. It’s in the lyrics she pens at home. It’s in the way she lights up when talking about her students or singing about her truth.

With a heart full of music and a voice that won’t quit, Jenna Deweese is just getting started. She’s already making an unforgettable impact, both on and off the stage.

Keep up with Jenna and other artists like her via Loud and Heavy Booking.