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Caillat soon met producer Mikal Blue, who hired her to sing on techno songs used at fashion shows.Caillat began playing the acoustic guitar at age 19, and Blue helped her record her first song. I was glad, when I auditioned, that they said no." Caillat's debut album, Coco was released in 2007.In 2008, she recorded a duet with Jason Mraz, "Lucky", which won a Grammy.Caillat released her second album, Breakthrough, in August 2009.The album features collaborations with Brad Paisley, Gavin De Graw, Justin Young and Jason Reeves.

Her father, Ken Caillat, co-produced Fleetwood Mac's Rumours (1977) and Tusk (1979) albums.Breakthrough was nominated for Best Pop Vocal Album at the 2010 Grammy Awards.She was also part of the group that won Album of the Year at the 2010 Grammys for her background vocals and writing on Taylor Swift's Fearless album.The second single, "I Never Told You", was released in February 2010.Caillat released two Christmas songs for the 2009 holiday season: the standard "Have Yourself a Merry Little Christmas" and the Beach Boys song "Merry Christmas, Baby".In the episode broadcast on October 3, 2011, Caillat sang Gore's 1963 hit, "It's My Party".

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