With a career trajectory like Colbie Caillat’s, it’s hard to imagine a time when she held back on sharing her voice. “I started singing really young; I would always sing in my bedroom in my house growing up,” she tells American Songwriter about her childhood days in Malibu, California.
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Her father, Ken Caillat, has left an indelible mark on the music industry as the producer of Fleetwood Mac’s iconic Rumours album, along with Tusk and Mirage. Her parents met at the Village Recorder studio in Los Angeles, where the band recorded Rumours. Caillat’s mother, Diane Leineke, also worked there and assisted Ken while he was recording Rumors. “My parents were like, ‘If you want to be a singer, you should learn how to play an instrument and be a songwriter. It’s a better career if you can have all of that,’” she says.
Soon, the aspiring singer started taking vocal, piano, and guitar lessons and, at 19, even auditioned at the Rose Bowl for season two of American Idol. “I was talked into auditioning,” she recalls, describing herself as “very shy” and “introverted,” adding that she didn’t have much performance experience outside of a couple of school talent shows. “I wasn’t right for it,” she says. “I wasn’t comfortable. They said ‘no’ instantly.” A year later, she re-auditioned, this time with her future hit “Bubbly,” but got rejected again.
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Around the time of her Idol audition, Caillat wrote her first song (a track called “Someday,” which she says she plans to release someday). A friend then started posting the songs she was writing on MySpace, which garnered an online fan base. Within a year, her career started to take off. Many of the songs that fans were watching her record in her bathtub ended up on her 2007 debut album, Coco(one of her many nicknames).
As her career gained momentum, Caillat recalls her father telling her, “‘You’re about to get on a really fast freeway, and it’s really hard to get off. It all flies by, and there are all these things coming at you.’
“My family and my friends have always been very close. I still have my best friend since I was 10 years old, and that’s helped me through this journey. I always have them to remind me of my childhood.”
Despite the rejection she faced at the Idol auditions, Caillat continued to build her fanbase one song at a time, with “Bubbly” opening up new doors of opportunity. “Listeners on MySpace from around the world chose my song. I got a record deal because they chose it, so it felt very much like it allowed me to grow with it,” she says.
“Bubbly” took on a life of its own when it was released as the first single off Coco, reaching the Top 5 on the Billboard 200 and hitting No. 1 on the Billboard Top Alternative Albums and Top Rock Albums charts. A month after the album’s release, she was on tour opening for Goo Goo Dolls and Lifehouse. “I had this huge opportunity that was just thrown in my lap,” she says, adding that it was the first time she had performed on an arena stage and was “so green and so nervous.”
The singer’s stage fright was so intense that she had a therapist and stage coach on the road with her, going so far as to have the stage coach talk into her earplugs and tell her how to speak to the audience. “I would stand there with my eyes closed, and she’s like, ‘You have to open your eyes. You have to talk to the audience,” Caillat recalls. But her songwriting helped heal the stage fright, citing her 2014 single “Try” as speaking to that feeling. “I started telling the audience about those fears, my stage fright, and I actually started getting comfortable on stage,” she says. “Every show that you do, the more you get comfortable and learn about yourself. I learned along the way.”
Letting the process guide her is what led Caillat to her 2025 album, This Time Around, a project that’s six years in the making. Caillat originally planned to rerecord a selection of her greatest hits in 2019, but the timing didn’t pan out. “I wanted to reimagine the versions of all my old singles that I still sing and how we sing them live,” she says. “I sing a lot differently than I did at the very beginning of my career, so when I listen back to the old recordings, I’m like, ‘I want to update them.’”
The idea expanded into turning her famous singles into duets, which then developed into a full-fledged duets album. The dozen songs find a range of country artists–including Maren Morris, Walker Hayes, and Russell Dickerson–lending their voices to several of Caillat’s signature hits, while some of her old friends, such as Gavin DeGraw and Jason Mraz, appear alongside three new originals and a cover of Post Malone’s “Circles.”
Caillat tapped several country artists for This Time Around, a genre where she has been making her presence known since moving to Nashville in 2016. She continued to advance into country territory as part of the band Gone West, alongside frequent songwriting collaborator Jason Reeves, Justin Young (her former fiancé), and Nelly Joy. The group disbanded in 2020.
“It was a long progression,” she says of venturing into country music. Though she didn’t grow up listening to country, the Grammy Award winner has spent much of her life traveling to Hawaii with her family, where the steel guitar is prominent. “I really felt like it started to become home in country music. The way that people write here, the songwriting is brilliant, and the musicians are incredible. Everyone works together,” she says.
The sense of community is palpable on This Time Around, as Caillat was intentional about pairing the personality of the singer with that of the song, though many of the artists requested to appear on specific cuts. Hillary Scott of Lady A asked to sing on “Try” because she often sings it with her daughter, while Morris picked “Fallin’ For You” and Mitchell Tenpenny claimed “Realize,” a song he said he often sang in high school.
Having known Hayes personally (she’s a featured vocalist on his 2025 album 17 Problems), Caillat knew that his upbeat personality matched “Brighter Than the Sun” (he even ad-libbed the “count me in, C” at the beginning). Caillat reveals she was stumped trying to figure out who could sing on “Bubbly,” until she landed on Amos Lee, applauding how he brought “some dynamic” to the track, while praising Tenpenny for adding a “soulful” vibe to “Realize.”
“What’s so fun about singing these old songs is finding new meaning in them,” she says, nodding to “Realize” and “I Never Told You” as songs that have resonated with her across time. “They pull at your heartstrings. A lot of them, I find the new meaning in what I’m experiencing in life. To know that [the artists] loved these songs, they wanted to sing on these songs; everyone brought their flair to every song that they sang. It all fell into place.”
As for the originals–“Live Without You” featuring Maddie & Tae, “Can’t Say No” featuring Ryan Hurd, and “Kinda Single” with Lee Brice–Caillat matched her songwriting prowess with fellow heavy-hitters, including Hurd and Liz Rose. The singer notes that on her previous album, Along the Way, she brought the majority of ideas into the writing room, while this time around, she was open to the suggestions of her co-writers.
“I like to start by myself because I still get shy, and it’s hard to be vulnerable with ideas, but I also will bring an idea into a room,” Caillat says of her songwriting style. The new tracks are largely breakup-inspired, with Rose helping to write “Live Without.”
During the writing session, Caillat says she told Rose, “‘I don’t really know what to say anymore.’” To which she says Rose replied, “‘There’s always something to say.’
“I was telling them about the breakup and how you think the world’s going to end, and everything reminds you of that person. Then slowly, it starts to shift. [Rose] has a way of hearing you and hearing what you’re wanting to express and saying it in the most beautiful, eloquent, condensed way.”
Meanwhile, “Kinda Single” was inspired by a conversation that took place between Brice and one of the album’s producers moments before Caillat walked into the studio. Lee asked if she was married or single, and the producer replied, “She’s kind of single,” which Lee then pitched as an idea for the writing session.
“I think it’s nice to be able to add some freshness to it,” Caillat says of the three originals on the album. “We’ve written many breakup songs, we’ve listened to all of the variations, but somehow there are still new twists and perspectives to write about. They’re all what I was experiencing at that time.”
This Time Around serves as much of a reflection on Caillat’s vast career as it does breathing new life into it, showing the progression from a shy young singer into a celebrated icon. “It’s so hard as you’re growing and learning yourself and everything’s moving so fast and you’re being presented with different ways of how you can release music,” she says. “It’s hard to know yourself and take the time to actually sit and know when to say no. Looking back and wishing I could have taken a deep breath and had more time with my thoughts, it’s been a long journey. I felt like I had to do it for everyone else, and now I’ve learned to do it for myself.”
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