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.The parade featured acts like Miley Cyrus and the High School Musical cast.She and Musso performed a sketch based on a Hannah Montana episode. It earned her a Young Artist Award nomination in 2008 for "Best Performance in a TV Movie, Miniseries or Special Leading Young Actress".Osment expanded her repertoire into pop music and alternative/indie rock where she has recorded teen pop hits like "I Don't Think About It", "If I Didn't Have You" alongside her Hannah Montana co-star Mitchel Musso, and "Once Upon a Dream".Osment entered the world of music recording soundtracks for movie singles and Disney albums.On October 26, 2009, Osment release her debut extended play, All The Right Wrongs, with six songs in the standart edition and eight songs in the deluxe.The EP peaked at number 117 at Billboard Top 200 and number 1 at Top Heatseekers Abouy 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.
In 2008 she starred in the film Soccer Mom, and was ranked on number 1 on Parade magazine and Forbes to Hot Kid Stars To Watch list.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.When Miley was Hannah, Lilly was under the alias Lola Luftnagle.In 2002, Osment made her film debut as Gerti Giggles in Spy Kids 2: The Island of Lost Dreams which grossed 9 million globally and for which she won the "Young Artist Award" for best performance in a feature film.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.