Lain acted in her first adult film in 1991, titled Wild at Heart (not to be confused with the 1990 film of the same name). In 1993, Lain did her first hardcore film, The Original Wicked Woman, for Wicked Pictures, which became 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. In 1997, she appeared in Orgazmo, a non-pornographic mainstream movie directed by Trey Parker.

In 1999, the band Bloodhound Gang released a song entitled "The Ballad of Chasey Lain" about an obsessive stalker of Lain who writes her a series of sexually explicit letters.

Lain 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 two years on hiatus, she returned to adult films. Her first film upon return was titled Chasey's Back. On February 10, 2007, Lain launched a new company, Forbidden Cinema, to produce Chasey Reloaded.