Boyle started her acting career in 1988 with a part in Earth Girls Are Easy and had her first starring role, in 1994's Midnight Tease and the women in prison film Caged Heat 3000. She is sometimes credited as Lisa D. Boyle, Lissa Boyle, Lisa Boyles, Cassandra Leigh, or Cassandrea Leigh. She has appeared in several other movies, including cameos in Lost Highway and Face/Off and more substantial roles in direct-to-video softcore movies including Cinemax's I Like to Play Games which helped cement her loyal following. In addition to movies, she has also appeared on TV shows such as Married... with Children (playing Fawn, one of Kelly Bundy's friends, in five episodes), Dream On, Silk Stalkings and The Hughleys. She has also appeared in several music videos, including Aerosmith's "Falling in Love (Is Hard on the Knees)" as well as Warren G's "I Shot the Sheriff".