Ann entered the adult film industry in 1994. She quit porn in 1997 due to an AIDS scare in the industry, however she resumed performing in February 2006. In 2008, Ann starred as “Serra Paylin,” a parody of Republican vice presidential nominee Sarah Palin, in Hustler Video’s Who’s Nailin’ Paylin?, which was released on Election Day. Her directorial film, MILF Revolution, was released on August 5, 2013 and won the 2014 AVN Award for “Best MILF Release”. In August 2014, Ann reached out to fellow porn actress Belle Knox, also known as the “Duke [University] porn star”; in an interview conducted by XBIZ Lisa Ann said she could sympathize with the media attention that Knox had faced. In December 2014, she launched Porn Stars Boot Camp, a consulting firm, and also announced her retirement from performing in adult films; she had a breast reduction surgery shortly after retiring as part of her return to a normal life. Ann announced her comeback to the adult industry four years later and signed with Evil Angel.