In 2001, Chyler Leigh had the lead role in the film Not Another Teen Movie as Janey Briggs. She also appeared in Marilyn Manson's music video "Tainted Love", a song which appeared in the film. She was ranked #65 on the Maxim Hot 100 Women of 2002. In 2002, Chyler Leigh was cast in two short-lived TV series: Girls Club, in which she played lawyer Sarah Mickle, and That '80s Show, in which she played punk rocker June Tuesday. Following that, she joined the cast of Reunion in September, 2005.