Jenny Tolman opens up about new music, infertility, and her journey on CBS’s The Road

Country singer-songwriter Jenny Tolman took on a new chapter in her career as one of twelve artists featured in the CBS series The Road, a docu-competition produced by Blake Shelton and Taylor Sheridan.

The program, which is premiering on October 19 and streaming on Paramount+, follows rising country musicians on tour with Keith Urban, combining performance footage with personal stories.

In an interview with Entertainment Focus on October 13, 2025, she shared about her journey in the show.

“It was like a documentary meets competition,” Tolman said. “Viewers got to know us as people, our families, our stories, what drives us.” She added, “Performing original music was a huge opportunity, and having Gretchen Wilson as tour manager and Blake Shelton as host made it surreal.”

Tolman described the filming process as fast-paced. “It was like I was on The Bachelor,” she joked. “I knew everything that happened, but I couldn’t tell anyone.”

For her, the series represented more than professional visibility. “My story focused on being a mom on the road,” she explained. “I wanted to show that it’s possible to pursue your career and raise a family at the same time.”

Exploring personal stories through song on The Road

Alongside her television work, Tolman continued writing and recording music that reflected personal experiences. Her single “Maybe Next Month” addressed infertility, exploring themes of disappointment and hope.

The song was accompanied by a video directed by Randy Shaffer and received significant attention online.

“I didn’t even choose to write it,” Tolman said. “I woke up in the middle of the night with the song completely in my head.”

She explained that the lyrics were inspired by a close friend’s long struggle with IVF. “When I shared it on TikTok, it reached so many people,” she said. “Thousands of women commented with their own experiences, and it became something larger than I expected.”

Tolman viewed the response as proof that social media could serve a positive role in connecting audiences. “It showed me how beautiful that community side of it can be,” she noted. “You just have to nurture the good parts.”

The Road star Jenny talks about creating the world of Jennyville

Tolman’s creative identity extended beyond single songs. She and her husband, producer Dave Brainard, developed a fictional setting called Jennyville, a concept that allowed her to explore multiple characters and stories through music.

“He said, ‘We have all these characters in your songs, why don’t we give them a place to live?’” Tolman recalled. “That’s how Jennyville started. It gave me room to write freely and experiment with different perspectives.”

The concept informed albums such as There Goes the Neighborhood and Married in a Honky Tonk, which featured a mix of humor and observation.

Her lighter side appeared in the song High Class White Trash, known for its opening line:

‘There’s nothing like a sample at the bottom of a purse, to cover the Pall Mall reeking from your shirt.’

“I found some old perfume samples in my purse one day,” she said. “That’s where the idea came from — part real life, part imagination.”

Tolman also remained active in live music. She organized Cowgirls at the Cowboy, an annual festival in Jackson Hole, Wyoming, dedicated to female country performers. The event, founded by the late Bill Baxter, entered its fourth year in 2025.

“Bill wanted to create the nation’s first all-female country festival,” Tolman said. “He asked me to run it, and I’ve done that each year since.”

She confirmed that planning for future editions of the festival was already underway. “We start working on next year before this one even ends,” she added.

Reflecting on her busy schedule, Tolman acknowledged the challenges of balancing multiple creative projects while maintaining family life. “It’s not always easy,” she said, “but I feel grateful to keep telling stories — on stage, on screen, and through music.”

Stay tuned for more updates.