Colbie Caillat was born on May 28, 1985, and grew up in Malibu, California, immersed in music from an early age. Born on May 28, 1985, in Newbury Park, California, Colbie Caillat is a pop and jazz singer-songwriter, and was inspired by Roberta Flack's "Killing Me Softly," beginning to sing at the age of eleven. Her father, Ken Caillat, gave her an intimate connection to the music industry, since he was a co-producer of Fleetwood Mac's Rumours and Tusk albums, and encouraged her musical pursuits. She taught herself guitar as a teenager, and after briefly attending college, Caillat decided to leave college and pursue music professionally, moving to LA where she hustled to get her music out, playing acoustic shows and selling homemade CDs. Her early, breezy acoustic pop songs, largely co-written with songwriter Jason Reeves, would soon find an audience in an unexpected place: the internet.
That audience arrived through Myspace, where she posted several finished songs, generating little response until she uploaded a breezy, hook-laden track named "Bubbly," after which word of mouth spread and her page began pulling in a few thousand hits a day . For four months, Colbie Caillat was MySpace's number one unsigned artist, garnering over 14 million plays, and record labels began courting her until she signed to Universal Republic as her online friends surpassed 100,000. In July 2007, Caillat made her major-label debut with Coco, a summertime record suitable for both the coffeehouse and the beach. The single "Bubbly" became her signature song and remains her highest-charting song, her only song to peak within the top ten of the US Billboard Hot 100. The album itself was a commercial success, spinning off two additional singles while climbing to double-platinum status. Following that breakout, Caillat's career accelerated quickly through collaborations and further releases. In 2008, she recorded a duet with Jason Mraz, "Lucky," which won a Grammy Award, and she was also part of the group that won Album of the Year at the 2010 Grammy Awards for her featured vocals and writing on Taylor Swift's Fearless album. Her second album, Breakthrough, was released on August 19, 2009 through Universal Republic Records, and it debuted at number one on the Billboard 200, was later certified gold by the RIAA, and was nominated for Best Pop Vocal Album at the 2010 Grammy Awards. She continued releasing music through the following decade, including All of You in July 2011 and her first Christmas album, Christmas in the Sand, in October 2012, along with Gypsy Heart in 2014 and The Malibu Sessions on her own independent label in 2016. In 2018 she took a notable turn into a full band format, joining Justin Young, Jason Reeves, and Nelly Joy in forming the country group Gone West, which debuted at the Grand Ole Opry, releasing their single "What Could've Been" the following year. Gone West released its debut album Canyons in 2020, but Caillat officially left the band after two years, announcing the news on Instagram just four months after she and ex-fiance/bandmate Justin Young ended their ten-year relationship. On her own, Caillat's accomplishments remained substantial: she has won two Grammy awards, for album of the year with Fearless and best pop collaboration with vocals with the Jason Mraz-assisted hit single "Lucky," achieving four million cumulative album sales and eight multi-platinum records. Today, her legacy endures as a 2X GRAMMY Award-winning, 5X GRAMMY-nominated singer-songwriter whose music has garnered over 15 billion global streams. She has remained active into recent years, releasing new music including her 2025 album, This Time Around, a project that's six years in the making, revisiting her classic hits with fresh arrangements and continuing to tour, cementing her place as one of the defining voices of 2000s acoustic pop.
For those exploring this archive, Colbie Caillat holds a modest but meaningful place in Wayne Dennon's photographic record. Wayne photographed her show once, in 2010, capturing her at the height of her post-Breakthrough touring years, and the 31 images from that night remain part of this collection, viewed by archive visitors 24,172 times. It stands as a quiet but lasting piece of the larger story Wayne spent decades documenting, one bubbly, sun-soaked performance preserved among thousands of nights of live music history.
