In 2009 she signed with the Wind-up Records label and released "All the Way Up", the first single from her EP debut, All the Right Wrongs, released on October 26, 2009.
The EP debuted at the Billboard 200 and her songs reached the top positions on the Canadian Hot 100 and Radio Disney.
Osment also appeared in promoting Hannah Montana, Hannah Montana 's Backstage Secrets, which plays Lola in a fictional interview in the series canon .
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.
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 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.
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.
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".
Emily sings the chorus of the song Billy Ray Cyrus "You've Got a Friend" , from his album 2007 Home at Last.
Osment has also recorded a song titled "I Don't Think About It" in The Haunting Hour: Don't Think About It, for which they made a music video.
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.