If you were watching MTV in 2006 — or listening to country radio when Taylor Swift’s Fearless was at the top of the charts — there’s a strong chance you came across Cheyenne Kimball. After rediscovering the singer-songwriter on TikTok, Us Weekly reached out to speak to the former teen star about the days of getting advice from John Mayer, touring with Swift and picking up her guitar for the first time in a decade.
The ‘Cheyenne’ Days
After winning the TV show America’s Most Talented Kid at 12, MTV started documenting Kimball’s life for Cheyenne, an eight-episode docuseries, just shy of her 15th birthday. “No one in my life believed me that I was actually doing it,” Kimball told Us. “The show ended up coming out right around my 16th birthday, so it took like a whole year for that turnaround. … [It’s been] 20 years. I can’t believe it.”
At the time, MTV hadn’t completely transitioned from music content to full-on reality TV (though Laguna Beach and The Hills were top-rated shows), with The Osbournes, Newlyweds: Nick and Jessica, The Ashlee Simpson Show, Diary specials and, of course, TRL still keeping the music ties alive.
“I had watched Laguna Beach, I did watch The Ashlee Simpson Show, so I had an idea of what I was getting into. They stayed so true to me, which makes me very happy. I mean, there were some times when there was a little bit of drama made, but for the most part, it wasn’t super scripted or anything. That was my fear. I didn’t want things to come across fake. I didn’t want people to see just ‘drama, drama, drama’ because other than the fact that I was a child star, there wasn’t a whole lot of drama,” Kimball said. “I feel like they did that with Ashlee too.”
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Back then, the production wasn’t what reality TV has become. “It was one or two guys with a big camera. I was always like, ‘Do you need to rest your shoulder? Do you wanna take a break and eat a hamburger? I feel really bad, you’re just following me around all day with this really heavy piece of equipment,'” Kimball recalled. “You get to know each other really well when you’re in the same room together, pretty much 24/7.”
Cheyenne Kimball performs during “Music With Altitude” hosted by MHD January 11, 2006 in Breckenridge, Colorado. Michael Brands/Getty Images for MTVCheyenne’s first single, “Hanging On,” pulled double duty as the show’s theme song and marked her debut on the Billboard Hot 100. “It was a dream come true,” she said. “Because at that age, I wanted so badly to be taken seriously.”
Like any young star, Kimball began to get more attention, both from commenters online and A-list celebrities.
“I remember having MySpace back then and getting some comments that I still have burned into my brain that have never gone away. And no matter how many good ones I got, those one or two really bad ones stayed with me — and that’s heartbreaking,” Kimball told Us. “John Mayer himself told me not to read comments. He said,’That’s like listening in on a conversation you’re not a part of. You gotta stop doing that.’ He had asked me what’s the hardest thing about being a teen star? And I was like, ‘People are really mean online.’ But I had no idea what was to come [with social media], so I consider myself lucky.”
Kimball “wasn’t one to get starstruck” as a confident 16-year-old, recalling run-ins with Kelly Clarkson and the Jonas Brothers.
“[Kelly] was the sweetest person ever, and we were talking about going bowling, which we never did. I would really still love to do that — I wanna go bowling with Kelly Clarkson and live out my 16-year-old dream,” she said with a laugh. “It was really cool touring with the Jonas Brothers. They were just starting out when I was, and we did a mall tour together. I won’t tell you which one I had a crush on — but I did end up getting to hang out with him again later at the White House.”
Joining Gloriana
Two years after her debut album, The Day Has Come, was released, Kimball was asked to join a country band with brothers Tom and Mike Gossin and singer Rachel Reinert after relocating to Nashville from Los Angeles.
Joey Foley/Getty Images“Things were kind of dying down. I could feel the momentum slowing. And I was like, ‘I just want to go hide for a moment,'” Kimball said. Up until that point, her mother was acting as her manager. (But don’t worry, it wasn’t like that. “I called myself a stage child ’cause [people would ask], ‘You have a stage mom?’ And I’m like, ‘No, I’m a stage child. I forced my mother into this,'” she noted.)
Kimball then met Doc McGhee, who managed Mötley Crüe and Darius Rucker (who had just transitioned from Hootie & the Blowfish vocalist to solo country artist). McGhee introduced her to her current manager, Gary Bowen, whose roommate was “looking for a Stevie Nicks kind of girl for a four-part harmony group.”
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“I thought at the time it would be so cool to not have to carry everything on my own shoulders and share the vocals and the light and the experience with other people and share the experience with other people,” Kimball recalled. “I had to learn mandolin in two weeks.”
The foursome lived off pizza at an Oakwoods apartment in a “bootcamp” of sorts. “We were working on vocals, rehearsing, recording — it was very intense,” she said. “But we got so tight, like, our harmonies and everything we just clicked in.”
Gloriana’s first single, “Wild at Heart,” made waves on CMT and became the best-selling country music debut single of 2009. The band’s self-titled album also included the single “How Far Do You Wanna Go?” and peaked at No. 3 on the Billboard 2000. Gloriana subsequently hit the road with Swift and Kellie Pickler for The Fearless Tour, which ran from April 2009 to July 2010.
“The whole tour was a whirlwind,” Kimball said. “We were out for a year and a half [and] I feel like [at one point] we were on the road for 360 days [straight]. I went to my apartment for five days and I slept the whole time.”
Taylor Swift Through the Years
Still, Kimball has fond memories of Swift. “Taylor was really wonderful,” she said, recalling the now-insanely famous pop star buying her birthday gifts from Anthropology and complimenting her perfume when Pickler and Gloriana would join Swift on stage for “I’m Only Me When I’m With You.”
One regret from that time period was not recording one of Swift’s songs when given the chance.
“When I was younger, I was very stubborn. I didn’t want to cut other people’s songs. I was like, ‘Oh no, I wanna write everything.’ Taylor had mentioned that she had pitched me some songs and I was like, ‘I’m so sorry. I told my management and my label don’t give me anything. I’m writing it all. … Don’t take any offense to that. I probably didn’t even hear any of it. I’m sorry!'” Kimball recalled before, naturally, admitting, “I should’ve cut her songs!”
While she didn’t take Swift up on the offer, Miley Cyrus recorded one of Kimball’s songs titled “Four Walls” for 2008’s Breakout. Kimball got the call about Cyrus’ interest while on the tour bus with Gloriana. “It was a surreal moment and she did such a good job with it,” she said. “[When we finally met], she was just an absolute angel and gave me the biggest hug. She’s like, ‘Thank you so much for letting me have your song.’ And I was just like, ‘You’re Miley Cyrus? Take whatever you want.’”
Out of the Spotlight
Cheyenne Kimball during 37th Annual Songwriters Hall of Fame Ceremony – Show and Dinner at Marriott Marquis in New York City. L. Busacca/WireImage for Songwriter's Hall of FameNot long after the success of the song “Wanna Take You Home” in 2011, Kimball abruptly left Gloriana before the release of their second album.
“I struggled a lot just trying to find myself,” Kimball recalled. “It wasn’t even about the fact that I’d already had prior success or anything. I thought I would have something to relate to, but I didn’t feel like I had anyone to relate to. I felt very lonely sometimes. … I don’t think a lot of people realized how young I was. I didn’t realize how young I was. By the time I was 21, I had just gotten to a point where I needed a break. That’s why I disappeared for a while.”
“I didn’t really have those normal experiences of finding myself,” Kimball continued. “I had other people kind of telling me what I was. … I snapped a little bit and I didn’t have anything else to give.”
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Kimball went on a “whole journey” of “really deep diving into Cheyenne,” which included several different types of therapy (one-on-one therapy, group therapy and equine therapy).
“I had some brutal talks with people who made me realize that I had a mask on. I had no idea that I was just this all the time,” she said. “I went full blown Hannah Montana. I dyed my hair dark and just was like, ‘I’m hiding you.’ People didn’t recognize me anymore. And I think that was probably healthy for me at the time.”
During Kimball’s “massive break,” she didn’t even pick up her guitar once. “The first time I played after my break, I cried,” she told Us.
What’s Next
Now, after having daughter Nico, 8, Kimball is back with manager Bowen and writing music again.
“For the first time in my life, I feel like I’m solid and I’m ready to go and I have so much to say,” she said. “One song I’m working on right now is about being in a long-distance relationship ’cause that’s what I am with my honey right now. He lives in Los Angeles [and we’re in Tennessee]. He and I are actually writing it together. I have a song that I’m writing for my daughter, ‘I Hope You Dance’-esque. But also the Cheyenne in me is always there and she’s always gonna be there — the breakup songs it’s never gonna go away. Call it daddy issues, I don’t know. … I’m just like, ‘Gosh, why am I so angry?’ I’m actually a really happy person!”
Margaux PhotographyKimball describes the sound as country-pop. “I’m always gonna have pop in there, but country is just such a wonderful genre and they’re so open to female singer songwriters,” she said.
She’s also posting videos on TikTok and Instagram, covering her old music and other music under a series titled “Songs I Want My Daughter to Know.”
“I was so scared to put myself back out there again. I’m not gonna lie, I was terrified. I was like, ‘I’m gonna be eaten alive.’ But I’m shocked in the most positive way,” Kimball said of the response. “Everyone’s been so amazing. I couldn’t ask for a better response.”
She concluded, “I’m healed. I did the work. I think I could handle most of anything that life threw at me at this point.”
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