[3][4] Webster's first acting role was as part of the ensemble cast in the pantomime Cinderella at the State theatre in Sydney, at the age of five.

[5] The production starred Jo Beth Taylor as Cinderella, Nancye Hayes as the Fairy Godmother, Lochie Daddo as the Prince, Bert Newton as The Baron, and Bruce Spence and Paul Blackwell as the Ugly Step-sisters.

[6] At 10 years old, Webster played the Young Cosette in Les Misérables, and in 1999–2000 starred as Brigitta Von Trapp in a stage production of The Sound of Music, alongside Lisa McCune, John Waters and Bert Newton.

In August, following an elimination process, she was told by opening ceremony artistic director/producer David Atkins that the role was hers.

[7] At the age of 13, Webster played a major part in the opening ceremony, including performing the song "Under Southern Skies".

Webster signed a contract with BMG at the age of 13, after her success at the Olympics, and her first single "Strawberry Kisses" reached No.

[8] Webster and dance partner Sasha Farber were eliminated in week six of the series after judge Todd McKenney gave them a score of one out of 10.

[citation needed] In May 2007, Webster played the lead role of Sheila in a Perth production of the rock musical Hair along with Rob Mills and Cosima De Vito.

In September 2007, Webster raised eyebrows by performing as a wind-up doll at the Sydney gay and lesbian dance party Sleaze Ball.

[12] This and her October 2006 photoshoot appearance in men's magazine FHM were seen as an attempt to mature her image, but attracted wide ridicule given her previous role in the 2000 Olympics.

In January 2008, Webster announced she would be opening a performing arts school in February with brother Scott in a bid to help young people get into the industry.

[16][17] In 2001, Webster was named the face of Jager Cosmetics' "It's a Girl Thing" range for young teens.