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Osment's entry into the entertainment industry began in 1998, when she was cast in a commercial for flower delivery company FTD.

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She went on to co-star in the Emmy-nominated She also starred as Cassie in R. Stine's The Haunting Hour: Don't Think About It and the Disney Channel original movie, Dadnapped as Melissa Morris.Since then, she has gone on to do a number of roles, such as appearances on television shows like Touched by an Angel, Friends, and 3rd Rock from the Sun.Osment made her film debut as Gerti Giggles in Spy Kids 2: The Island of Lost Dreams (2002) which grossed 9 million globally, and for which she won the Young Artist Award for Best Performance in a Feature Film.In addition, Osment helped to design some of the pieces from the collection of clothing Hannah Montana Disney, which released the last part in the summer of 2006.She also had a voice over role in a movie called Holidaze: The Christmas That Almost Didn't Happen.

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