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Lain acted in her first adult film in 1991. The movie was entitled Wild at Heart (not to be confused with the 1990 David Lynch film by the same name). In 1993, Lain did her first hardcore movie, The Original Wicked Woman, for Wicked Pictures, famous as the first adult video to document a breast enhancement, before and after. In 1994, she became a contract actress for Vivid Entertainment, where she gained her major success with titles like Chasey Loves Rocco and Chasey Saves the World. She had her own line of lesbian videos, the Chasin' Pink series. In 2002, she filmed her last film with Vivid Entertainment, Chasin' Pink 6, and took a break from the industry. In 2004, after 2 years on hiatus, Lain returned to adult films. Her first film upon return was entitled Chasey's Back. Chasey went on to perform in her first interracial scene with Mr. Marcus in Black in White 2 in 2005. On February 10, 2007, Chasey Lain launched a new company, "Forbidden Cinema", to produce Chasey Reloaded. Chasey made the Top 50 Pornstars of All Time list in AVN Magazine in 2002.