Songs were often mixed at the console in her Malibu beach house, filling the corridors with the sounds of Billy Idol, Pat Benatar, and other '80s pop/rock staples. Caillat took piano lessons as a child, but lacked significant inspiration until she turned 11 years old and became enthralled with Lauryn Hill's performance in Sister Act 2. Immediately realizing that she wanted to be a singer, she started taking vocal lessons and soon met Mikal Blue, a producer who had previously worked with Five for Fighting and Carrie Underwood. Blue hired her to sing on several techno songs that were to be used in runway models' shows, and the two cultivated a professional relationship. At 19, Caillat picked up an acoustic guitar, and the two recorded the first song she composed.

As the collaboration thickened, Jason Reeves entered the picture and lent his artistic know-how to the songwriter's developing skills. Caillat wrote the basic melodies, often composing in her bathroom due to the reverb-heavy acoustics, and would then receive artistic input from Blue and Reeves. She posted several of her finished songs on MySpace, although little response was generated until Caillat uploaded a breezy, hook-laden track named "Bubbly." As word of mouth spread, her MySpace page began pulling in a few thousand hits a day; after she had accumulated 6,240 friends, Rolling Stone highlighted her as one of the top female artists on the networking site. For four months, Colbie Caillat was MySpace's number one unsigned artist, garnering over 14 million plays in the process. With such an appealing statistic on her résumé, record labels began courting the photogenic singer, and she signed to Universal Republic as her number of online friends surpassed the 100,000 mark.

In July 2007, Caillat made her major-label debut with Coco, a summertime record suitable for both the coffeehouse and the beach. "Bubbly" topped the singles charts in several formats, transforming the singer from an Internet sensation to a mainstream presence. Coco spun off two additional singles while climbing to double-platinum status, and Caillat celebrated her star success by duetting with Jason Mraz, touring with John Mayer, and collaborating with Taylor Swift. Two years after Coco's release, she returned with a second record, Breakthrough, and scored another Top 40 hit with "Fallin' for You." The album went gold and was followed two years later by All of You, another summery collection of pop songs written with the likes of Ryan Tedder, Toby Gad, and "Bubbly" co-writer Jason Reeves. "Brighter Than the Sun," the second single pulled from the album, was the record's biggest hit, topping Billboard's Adult Contemporary charts (it peaked at 47 on the Hot 100). Caillat released the holiday album Christmas in the Sand in the fall of 2012; the album reached number four on Billboard's Top Holiday Albums and 41 on the Billboard 200.

Caillat began work on her next album in 2013, with the first fruit of her labor, "Hold On," appearing in November 2013. An EP called Gypsy Heart: Side A showed up in June 2014 and, as that title suggests, it was the first half of a full-length album called Gypsy Heart, which was released in September 2014. Produced in part by Babyface, the album was a conscious shift to poppier, radio-friendly material. The album debuted at 17 on Billboard's Top 200 and its biggest single, "Try," peaked at six on their adult contemporary chart.

Caillat parted ways with Republic Records after Gypsy Heart and formed her own label, PlummyLou, with the intent of releasing The Malibu Sessions. Recorded prior to Gypsy Heart but rejected by Republic, The Malibu Sessions reconnected Caillat to her beachy sound, and saw release in October of 2016. ~ Jason Lymangrover