Jenny Tolman Takes Viewers Behind the Scenes of The Road
Singer-songwriter Jenny Tolman is taking her music, and her life on the road, to a whole new level with her appearance on The Road, CBS’s brand-new touring competition series. The show, produced by Taylor Sheridan, Blake Shelton, David Glasser, Lee Metzger, and Keith Urban, follows 12 emerging artists as they compete to open for Urban at live venues across the country.
The docu-style competition premiered October 19 and airs Sunday nights on CBS and Paramount+. In this unique format, contestants perform live in front of real audiences, with their fate determined not only by crowd votes but also by industry legends including GRAMMY winners Keith Urban and Gretchen Wilson, as well as guest mentors like Blake Shelton, Jordan Davis, Karen Fairchild, Dustin Lynch, and Brothers Osborne.
In a recent interview with Country Evolution, Tolman shared what it was like to live, perform, and learn under the pressures of a real touring schedule, all while competing for the ultimate career-changing opportunity.
Balancing Music and Motherhood
For Tolman, one of the hardest parts of the competition wasn’t the performing. “Probably being away from my son,” she admitted. “That was the first time that I had ever left him. He’s two years old. Really, really hard to be away from him for so long because he usually always comes on the road with me.”
Despite the challenge, Tolman found strength in the shared experiences of her fellow contestants, since there were a few other parents on the show. She explained “We could lean on each other and understand what each other was going through. So that was definitely a blessing.”
Technology also helped bridge the distance. “FaceTime is wonderful,” she added. “We talked every day, and that definitely made it a lot easier.”
Learning from Country Legends
Tolman says performing on tour with Keith Urban was a master class in musicianship. “Watching Keith Urban every night was like a master class in performance and audience control,” she shared. “He’s insane at what he does. That was the greatest learning experience, getting to learn from him hands-on was pretty powerful.”
She also credited GRAMMY-winning country star Gretchen Wilson, who served as the show’s “Tour Manager,” with offering advice that resonated deeply. In the first episode, Wilson is seen guiding contestants during their soundchecks, from encouraging them to move closer to the microphone to helping them connect emotionally with their songs. Her goal was to elevate each artist’s performance.
“One of the coolest things about getting to talk to Gretchen was learning how many doors she broke down for women in country music,” Tolman said. “Just staying true to who you are and being strong and confident as a woman in this industry is so important. Hearing her stories directly from the source was super inspiring.”
After the first episode, Tolman found herself landing safely in the middle group, out of the elimination zone, but the competition was just heating up. A preview for week two teases a playful challenge when Tolman experiences a costume malfunction on stage, reminding viewers that live performance comes with unpredictable moments. On The Road, audience votes are key, but the final decision comes from Keith Urban and Blake Shelton, who choose which contestant leaves from the bottom three after Keith’s set has wrapped and the crowd has gone home. Knowing the stakes (and that so much rides on both audience response and mentor input) adds an extra layer of intensity to each performance.
A Storytelling Approach to Every Stage
Known for her sharp wit and storytelling style, Tolman says connecting with the audience has always been at the core of her performances.
I love music that tells stories,“ she explained. “I always love to tell the story about the song and kind of get the audience engaged with the story before they even hear the music.” Tolman said that the intent is to take them along for the journey before the song even begins.
She describes her sound as “traditional country, very character-driven storytelling, tongue in cheek,” with a nod to one of her biggest influences, Roger Miller. “He had a lot of humorous music, but it was always wrapped around a meaningful message,” Tolman began. “He was really brilliant at being able to capture an audience’s attention through laughter and by doing so, you relax them, and then once they’re comfortable with you, they’re open to hearing what that actual message of your song is.”
Behind the Scenes: Fire Alarms and Friendship
While The Road captures the high-stakes energy of life on tour, Tolman says it also had its share of lighter moments. One memorable behind-the-scenes story happened in Fort Worth, when the dry air wreaked havoc on everyone’s voices.
Watch Now
“I turned my shower on all the way hot to steam up my room and get some moisture going,” she laughed. “It steamed up so much that it set the fire alarm off. The poor hotel manager had to come up and wave a towel at it to stop it. I was just trying to get my vocal cords warm!”
Looking Ahead
Regardless of who wins, Tolman says the show has already been life-changing. With the exposure of being on a national program, they have the opportunity to reach so many more people. She said, “I’m just very grateful, I think for each of us, it’s going to be a career booster no matter what.”
She hopes fans see The Road as a more authentic look into the life of a musician. “I mean, it’s gonna be unlike anything people have ever seen before,” she said. “They’ve never been shown this reality. They’ve gotten to see the shiny stages and things like that with music competitions, but actually getting to see the real life of what goes into being a touring artist and musician, it’s going to be really cool and impactful. You’re going to get to know everybody’s story really well, which is what I’m most excited about, just really getting to connect with people through that and and having them get to know us as artists and humans.”
Outside of the show, Tolman continues to build her brand as a singer, songwriter, and festival curator. She recently hosted her fourth annual Cowgirls at the Cowboy Festival, the nation’s only all-female country music festival, at the Million Dollar Cowboy Bar in Jackson Hole, Wyoming. This year’s lineup included Ella Langley, Trannie Anderson, Willow Avalon, and Mae Estes.
Tolman shared that it was an honor to carry on the legacy of the late Bill Baxter, the original creator of the festival. A few years ago, he called her with an idea for an all-female country festival at The Cowboy and asked her to be the face of it. She described the opportunity as both beautiful and humbling, saying she felt honored to help bring his vision to life. Since its debut, the festival has featured an impressive lineup each year, with Carly Pearce headlining the first year, followed by Lauren Alaina, Ashley McBryde, and most recently, Ella Langley. Tolman shared that plans are already underway for next year’s event and called the experience a “pinch me” moment in her career.
About Jenny Tolman
Jenny Tolman has built a world of her own where humor, heartache, and southern charm collide. With two acclaimed albums, There Goes the Neighborhood and Married in a Honky Tonk, Tolman has been praised by Billboard and Rolling Stone Country for her clever, story-driven songwriting. Beyond performing, she’s an advocate for women in country music through her annual Cowgirls at the Cowboy Festival. Her latest single, “Maybe Next Month,” continues her tradition of heartfelt, emotional storytelling.
