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 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.
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.
Emily also made a brief cameo in the Smash Mouth music video All star, as the girl in the referee uniform.
In October 2010 she began her Fight or Flight Tour, whose first performance took place in São Paulo, Brazil.
Osment also appeared in promoting Hannah Montana, Hannah Montana 's Backstage Secrets, which plays Lola in a fictional interview in the series canon .
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.
She recorded a song called "Hero in Me" for the Disney Channel original movie, Dadnapped and also filmed a music video to accompany it.
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.