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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.
On December 25, Osment hosted the Walt Disney World Christmas Day Parade with Hannah Montana co-star Mitchel Musso.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.1 on Parade magazine and Forbes to Hot Kid Stars To Watch list. 1 at Top Heatseekers About the album, Osment said: "The songs on the album are from four different people, I wrote with four different people, and they all had to fit on the album together…I kind of just did my own thing.On October 26, 2009, Osment release her debut extended play, All The Right Wrongs, with six songs in the standard edition and eight songs in the deluxe. I listen to a lot of Alanis Morissette, I kind of got inspired from her and her song "Jagged Little Pill" …There's a lot of edge to (Emily's album)…I love hearing the guitars and the drums in the songs".