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She started off on her path to stardom with a song called "Bubbly" which she showed off on before working on a song which was ultimately, the super successful "Bubbly" and putting it on My Space which was picked up by a recording company.She was top charting unsigned artist for four consecutive months.For this album she did a song with Jason Mraz called Lucky which is a Sickeningly Sweethearts song mentioned on it's trope page. Sometime during this she ultimately broke up with Ky (A guy mentioned in her Thanks You's in Coco and Breakthrough).This person she had a complex relationship going into stardom. Caillat performed "Brighter Than the Sun" on Disney Channel's So Random! Caillat appeared in the third episode of the NBC television series The Playboy Club as 1960s singer Lesley Gore.
This was an experimental album for her, she experimented with symphonies, electric guitars and choirs on the album.She also did a song called "Somethin' Special" for the Bejing Olympics in middle to late 2008 and this song featured on it's soundtrack.Soon after the release of this album she finished her album called "Breakthrough".His fourth album, Love Is a Four Letter Word, peaked at number 2 on the Billboard 200, his highest-charting album to date.Mraz has won two Grammy Awards and received two additional nominations, and has also won two Teen Choice Awards, a People's Choice Award and the Hal David Songwriters Hall of Fame Award.