RISON - When Jesse Ott takes the stage at the upcoming Rison in the Fall Festival Saturday, Oct. 10, listeners will hear far more than a simple country set.
They will experience the musical culmination of a journey that spans the rural dirt roads of Scott, Arkansas, the bustling art school scene of Chicago, and nearly a decade of high-stakes songwriting and waiting tables in Nashville.
Operating under the stage moniker Whoa Dakota, Ott represents a rising wave of Arkansas artists returning to their roots with newfound perspective, mature craft, and standard-setting independence.
Ott shares that journey in the latest episode of the Free Range Conversations podcast, which kicks off a series of episodes featuring the performers of this year’s festival.
The full episode is streaming now on Apple Podcasts, Spotify and ClevelandCountyHerald.com
The Story Behind the Name
For many listeners, the stage name "Whoa Dakota" evokes images of western rodeos and runaway horses. But the real story behind the name traces back to Ott’s early years in Music City.
After relocating to Nashville, where she lived for nine years, Ott settled into the Sylvan Park area, often referred to as "The Nations."
"Each street was a different state, so I lived on Dakota Avenue. The guys I was playing with at the time were really into the Black Crowes, and they have a song called 'Whoa Mule.' So we just put those two together, and that was that,” she said.
A Childhood Between Two Worlds
Ott’s diverse musical sensibility stems directly from her upbringing in Arkansas, which balanced urban culture with authentic rural traditions. Her parents were divorced, creating a childhood split between town and farm.
"My mama, she was a city girl—she lived in Park Hill, North Little Rock. My dad was a country boy, so he always has had a farm. His farm was in Scott, on Hattie Lane—a road he built and named after my grandmother,” she said. “Growing up was cool because I got to have the best of both worlds."
Those memories range from wild farm rides in her father's chuckwagon at three years old to weekend concert trips to Memphis with her mother, who would always figure out a way to get her young daughter into blues shows.
This dual upbringing laid the groundwork for a rich tapestry of musical influences—from 90s country icons like Reba McEntire, The Chicks, and Jo Dee Messina to John Prine, Bonnie Raitt, Miles Davis, Erykah Badu, and Stevie Nicks.
The Journey: Chicago, Nashville, and Modern Realities
At age 18, Ott left Arkansas to attend DePaul University in Chicago as an English major. Inspired by local musicians, she transferred to Columbia College in Chicago, earning a degree in vocal performance while singing in funk, neo-soul, and blues-rock bands. From Chicago, her path led straight to Nashville.
In Nashville, Ott balanced songwriting and recording with gigging and waiting tables at fine-dining establishments like Park Cafe, where she routinely served country legends like Dolly Parton, Reba McEntire, and Tanya Tucker.
While in Music City, Ott joined the Nashville Songwriters Association and gradually shifted toward country music—a style she was raised on but had previously judged as overly limiting.
"When I was younger, I wanted to try things I didn't know about. During COVID, I came back to my personal roots of country and realized I had just been a snob. I realized in writing country why it's so special, why those changes remain, and how much freedom you have to tell a story within that traditional structure."
However, the intense pressure of the Nashville "rat race" eventually took a toll. Between expensive pay-to-play band setups and constant comparison, the onset of the COVID-19 pandemic and a personal breakup prompted Ott to re-evaluate her path and move back home to Arkansas.
"I did feel a little bit of failure when I decided to move home from Nashville. I had to look at myself and say: 'Jesse, you did do the thing. Just because you didn't fill out Bridgestone Arena doesn't mean you weren't every bit as much a musician as Kacey Musgraves or anyone else. You toured, you wrote, you recorded, and you're going to do it forever.' My perspective has really shifted since I let go of gripping things so tightly,” she shared.
Embracing Creative Freedom & A New Record Strategy
Since returning to Arkansas, Ott has built a solid, dedicated band and established a sustainable balance between her art and life.
By day, she works in sales for Ben E. Keith, a food distribution company—a full-time role she loves that connects her directly with regional chefs and restaurant creators.
Musically, Ott is currently working on fresh material following her classic country EP, Rhinestones and Rodeos.
Rather than rushing a traditional full-length album release, Ott and her band are embracing modern streaming dynamics.
"The good thing about not having a label or manager to answer to is that I get to kind of do it how I want to do it, and it's fun... We can split it into a few singles, two EPs, and then one big album. There are really no rules."
Her upcoming sound bridges classic traditional country elements—1-4-5 chord structures, tongue-in-cheek storytelling, and soaring vocal runs—with nuanced, journalist-style indie-songwriter influences reminiscent of early Jewel or Phoebe Bridgers.
Kicking Off the Rison in the Fall Festival
Festivalgoers at this year's Rison in the Fall Festival are in for an intimate, high-energy performance.
Recommended to festival organizers by fellow Arkansas music powerhouses Cliff & Susan, Ott will kick off the festival's musical showcase at 1 p.m. Her set will feature a classic acoustic-and-pedal-steel setup alongside backup vocals, pulling tracks from Rhinestones and Rodeos as well as brand-new, unreleased material.
Performing in Rison carries a distinct historical resonance. Located in Cleveland County—the birthplace of country music legend Johnny Cash—the festival stage on Main Street sits along the exact path Cash took during his famous 1976 homecoming concert.
Ott expressed excitement about exploring Rison and joining the vibrant regional music ecosystem that continues to champion Arkansas-grown talent.
"I'm down for any place I get to explore. We might even need to throw in an obligatory Johnny Cash cover while we're there!"