It was Colbie Caillat’s destiny to be one of those quintessential California singer/songwriters. Born in Malibu in 1985, the artist responsible for “Bubbly,” one of the most lovable hits of the 2000s, spent her childhood living the Golden State dream. When she wasn’t busy taking voice lessons or studying piano, she was soaking up rays on Southern California’s world-famous beaches. She even spent time hanging with Fleetwood Mac—whose landmark album Rumours was coproduced by her dad, Ken Caillat. Her road to fame wasn’t smooth, however. After two unsuccessful auditions for American Idol, Caillat began posting her impeccably crafted tunes to MySpace, in the process becoming one of the social-media network’s most popular unsigned talents. One of those tracks was “Bubbly,” which soon served as her first major-label single. Zipping up the charts in 2007, the breezy anthem placed her smack in the middle of a new generation of singer/songwriters, along with Jack Johnson, who were creating modern beach music rich in feel-good pop hooks and warm acoustic tones. Two years later, a collaboration with Jason Mraz yielded the similarly upbeat “Lucky.” Yet Caillat—whose instantly recognizable voice is as versatile as it is heartfelt—wasn’t about to be pigeonholed. The 2014 album Gypsy Heart, coproduced by Babyface, found her embracing sparkling electronic textures. In the late 2010s, Caillat made yet another bold shift, relocating to Nashville, where she formed Gone West with then fiancé Justin Young. The short-lived yet commercially successful group notched the hit “What Could’ve Been” in 2019. And while the tune saw Caillat and crew diving into country pop, its gloriously sunny harmonies were proof that the singer/songwriter will always have California in her soul.