Bennett was born in Naples, Florida as Haley Keeling, the daughter of Leilani Dorsey Bennett and Ronald Keeling. She went to school in Stow Ohio at Lakeview Intermediate, Kimpton Middle and Stow-Munroe Falls High School in Stow, Ohio and later studied music and acting while attending Barron Collier High School She later attended Barbizon school for modeling and acting. She and her mother moved to Los Angeles, California to pursue her career in the summer of 2005 during her senior year.She acted everyday till her graduation.
Bennett made her film debut as the pop music singer Cora Corman in the 2007 romantic comedy Music and Lyrics, alongside Hugh Grant and Drew Barrymore. Bennett sang several songs for the Music and Lyrics soundtrack, including "Buddha's Delight" and "Way Back into Love." Fragments of "Entering Bootytown" and "Slam" are heard during concert scenes in the movie. "Invincible" can only be heard during the end credits and is only a minute and a half long.
She appeared in the February 2007 issue of GQ in the GQ/Features section. Also that year, she signed with 550 Music/NuSound Records (part of the Epic Records family of labels), and began working on her first album with the aid of singer/songwriter Shaley Scott.
She signed a three-picture deal with Warner Brothers Pictures and starred in her second and third movies, College and The Haunting of Molly Hartley (2008), in which she played the lead role. She also made a cameo in the movie Marley & Me.
Bennett performed her first live concert at The Mint in Los Angeles on June 19, 2008. Bennett appeared in the October issue of Teen Vogue in the Young Hollywood section. She is also in the movie "Ugly" that will premiere May 2009.
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