Osment's entry into the entertainment industry began in 1997, when she was cast in a commercial for flower delivery company FTD. From there she went to play the role of Biba in the children's preschool television series Biba Bear in 1998. She featured 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. 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 appearance in the Smash Mouth music video All Star as the girl in the referee uniform. 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. She also did the role of Tara Sparkler in Goosebumps. Osment made her film debut in 2002 as Gerti Giggles in Spy Kids 2: The Island of Lost Dreams, a role 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 $197 million worldwide. Osment did a voice-over role in the Disney movie Lilo & Stitch 2: Stitch Has a Glitch and also a voice role in Edward Fubbwupper Fibbed Big.