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Osment also appeared as Cassie Keller in The Haunting Hour: Don't Think About It (2007) and as Melissa Morris in the Disney Channel television film Dadnapped (2009).She starred as Taylor Hillridge in the ABC Family television film Cyberbully (2011) and as Roxie on the web television series Cleaners (2013–2014).She also did the role of Tara Sparkler in Goosebumps.Osment made her film debut in 2002 as Gerti Giggles in Spy Kids 2: The Island of Lost Dreams, a role for which she won the Young Artist Award for Best Performance in a Feature Film. Born and raised in Los Angeles, Osment began her career as a child actress, appearing in numerous television shows and films including Biba from Biba Bear from 1998-2002 before co-starring as Gerti Giggles in Spy Kids 2: The Island of Lost Dreams (2002) and Spy Kids 3-D: Game Over (2003).She is perhaps best known for her role as Lilly Truscott on the Disney Channel television series Hannah Montana (2006–2011) and appeared in the theatrical film based on the series, Hannah Montana: The Movie (2009).The video was released in Haunting Hour DVD and premiered at Cartoon Network.On December 25, Osment hosted the Walt Disney World Christmas Day Parade with Hannah Montana co-star Mitchel Musso.

In 2006, Osment got the role of Lilly Truscott in the Disney Channel series Hannah Montana, the best friend of Miley Stewart and girlfriend to Oliver Oken on seasons 3 and 4.Since 2014, Osment has starred as Gabi Diamond on the Freeform television series Young & Hungry, for which she has received three Teen Choice Award nominations.Osment came to prominence in music after recording songs for the soundtracks of her Disney projects, most notably a duet of "If I Didn't Have You" with Mitchel Musso in 2007 and a cover of "Once Upon a Dream" in 2008.She also had a voice over role in a movie called Holidaze: The Christmas That Almost Didn't Happen.She performed several songs for the movie, including "Don't Ya Just Love Christmas" and "One Day".

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