Colbie Caillat is getting candid. In the first episode of American Songwriter’s Off the Record podcast, host Lisa Konicki chatted with Caillat about her nearly two-decade-long journey in the music business.
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Caillat’s interest in music dates back to her childhood. Her parents were both in the music business. Her dad, Ken Caillat, even produced Fleetwood Mac’s famed LP, Rumours.
Despite her parents’ industry know-how, Caillat wasn’t pressured to join the family business. Instead, she would sing in her bedroom and perform in talent shows with her friends.
When Caillat was just 19, she started to take things more seriously. She signed up for vocal, piano, and guitar lessons. It was also at that age that Caillat decided to try out for American Idol. The audition didn’t last long.
“They just said no instantly. It was like we were at the Rose Bowl. There were thousands of people in the parking lot. You have to camp out overnight to get a spot in line… Our parents were there. It was wild,” she recalled. “I was nervous, and I just didn’t have the look. I didn’t have any of the things. Ten seconds in, they were like, ‘Next.’”
Despite the rejection, Caillat gave it another go the next year, auditioning with her song “Bubbly”, which went on to become a major hit.
“They said the same thing… They said no again,” Caillat said, before sharing why she “wasn’t right for the show.”
“I was very shy, introverted,” she said, noting that she “had never really performed before besides a couple of school talent shows.”
Colbie Caillat’s Early Career
While Idol wasn’t in the cards for Caillat, a career in music certainly was.
“I wrote my first song when I was 19,” Caillat recalled. “My friend put those songs up on MySpace. When I was 20, everything kind of took off.”
The people at Idol may not have responded to “Bubbly”, but the internet did. In fact, the online chatter got Caillat a record deal. From there, it was full steam ahead.
“I went on tour that next summer with the GooGoo Dolls and Lifehouse,” Caillat said. “That was my first time ever being on a stage like that… I had this huge opportunity that was just thrown in my lap.”
“[There are] a lot of friends I’ve had in the music industry where it takes them a lot longer to get to that place, and so they had a lot more practice and experience,” she continued. “I was just so green and so nervous.”
With the help of a therapist and a stage coach, Caillat made it through.
“Every show that you do, the more you get comfortable, and the more you learn about yourself,” she said. “I learned along the way.”
In 2008, Caillat teamed up with Taylor Swift to write “Breathe.”
“She’s brilliant. That was a long time ago. She was so young,” Caillat recalled. “I flew out from Nashville. She wanted to write with me. She had this idea she brought in the room.”
Caillat further noted of Swift, “She was so sweet. She brought me a gift. Her mom dropped her off.”
The song, which appeared on Swift’s sophomore album, Fearless, was nominated for a Grammy.
“I was just so impressed at her confidence, and her talent, and her wisdom in general, but especially at that age,” Caillat said. “I was just blown away. It was a really cool experience.”
Colbie Caillat’s New Duets Album
Most recently, Caillat released her new album, This Time Around.
On the LP, Caillat reimagined some of her biggest hits as duets with stars Maren Morris, Walker Hayes, Amos Lee, Mitchell Tenpenny, Jason Mraz, Hillary Scott, Chris Young, and Russell Dickerson.
“That’s what’s so fun about singing these old songs, finding new meaning in them,” she said. “They pull at your heartstrings a little bit.
As for how the pairings were made, it was a mix of Caillat asking artists to appear on songs and artists making requests for specific tunes.
Scott asked to sing on “Try” because it’s a song she sings with her daughter. Caillat, meanwhile, wanted Tenpenny on “Realize”, and he obliged, much to Dickerson’s dismay, as he had his eye on the tune. Dickerson ended up with “If You Love Me Let Me Go”, while Morris, who was initially slotted for Hayes’ spot on “Brighter Than the Sun”, appeared on “Fallin’ for You” instead.
A “tough” challenge came with picking the featured artist for “Bubbly,” a task that eventually went to Lee.
“I didn’t know who would fit that. Amos, I became friends with him last year, and I was nervous to ask him, but he said yes. He added such amazing, smooth vocals. It’s really cool. He just added some dynamic to that.”
The album also features a cover of Post Malone’s “Circles” with Gavin DeGraw, as well as three new songs—”Kinda Single” featuring Lee Brice, “Live Without” featuring Maddie & Tae, and “Can’t Say No” featuring Ryan Hurd.
“I just think it’s nice to be able to add some freshness to it,” she said of the new songs on the LP. “They’re all just very much what I was experiencing at that time.”
The Pop Star Has Developed a Country Fascination
Whether new songs or reimagined ones, many on the album have a country flair, a genre Caillat first dove into on her 2023 LP, Along the Way.
“It was a long progression,” Caillat said of her journey to becoming a country music fan. “I didn’t grow up with country music. I honestly wasn’t a fan of it until, like, 15 years ago or even less than that, maybe. It wasn’t around.”
When Callait started making some Nashville-based friends like DeGraw, she began to get more into the genre.
“The way that people write here, the songwriting is brilliant and the musicians are incredible… It’s a small town. Everyone works together. Everyone’s friends with each other. I’ve been here for nine years now, and it truly, slowly just started feeling like this is the kind of music I want to create. It felt natural.”
Photo by Danielle Del Valle/Getty Images
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