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She featured in many commercials, after which she made her acting debut in the 1999 film The Secret Life of Girls, starring Eugene Levy and Linda Hamilton.The same year, she co-starred with Glenn Close in the Hallmark Classic television film Sarah, Plain and Tall: Winter's End, a role that would lead a Young Artist Award nomination.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.
She performed several songs for the movie, including "Don't Ya Just Love Christmas" and "One Day".Osment also had a voice-over role in a movie called Holidaze: The Christmas That Almost Didn't Happen, which also featured the voices of fellow Disney Channel stars Brenda Song and Dylan and Cole Sprouse. She also recorded the song "I Don't Think About It" for the movie's soundtrack.Emily performed several songs for the film, including "Don't Ya Just Love Christmas" and "One Day". Osment also recorded a remake version of the song "If I Didn't Have You" with Mitchel Musso for the Disney Mania 6 CD. The two also filmed a music video for their remake.In 2003, she reprised her role in the third film of the Spy Kids series, Spy Kids 3-D: Game Over, which grossed 7 million worldwide.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.