According to an interview at the 2008 Grammys, she was writing some songs together with Eve 6.
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 then, she has gone on to do a number of roles, such as appearances on television shows like Touched by an Angel, Friends, and 3rd Rock from the Sun.
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.
Osment's entry into the entertainment industry began in 1998, when she was cast in a commercial for flower delivery company FTD.
From there she went on to feature 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.
After working in several television films in her childhood, she gained fame for co-starring as the character Gerti Giggles in Spy Kids 2: The Island of Lost Dreams and Spy Kids 3-D: Game Over.
She went on to co-star in the Emmy Award-nominated She also starred as Cassie in R. Stine's: The Haunting Hour Volume One: Don't Think About It and the Disney Channel Original Movie, Dadnapped as Melissa Morris.
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.
She currently stars in the Freeform television series Young & Hungry as Gabi Diamond.