Fenn began her career with a number of B-movies, including "The Wild Life" (1984, opposite Chris Penn), the 1986 skater film "Thrashin (opposite Josh Brolin and Pamela Gidley), the 1986 teen car action and revenge fantasy "The Wraith" (alongside Charlie Sheen and opposite Nick Cassavetes), the 1987 horror film "Zombie High" (alongside Virginia Madsen), and the "Beauty and the Beast"-inspired erotic movie '. She had a part in the 1985 cult teen-comedy "Just One of the Guys" in which she tries to seduce a teenaged girl who was disguised as a boy, played by Joyce Hyser. Fenn starred alongside Johnny Depp in the 1985 short student film "Dummies", directed by Laurie Frank for the American Film Institute. Fenn and Depp dated for three and a half years, subsequently getting engaged. In 1987, she joined Depp in a season-one episode of "21 Jump Street" called "Blindsided".