Andrews grew up in Milwaukee, Wisconsin, the youngest of four children. She attended a Baptist day school. After graduating from high school, Brittany stripped on the road for two years, including three months in Guam and three months in Tokyo where she earned $70,000. Brittany questioned Jenna Jameson in Jamaica about the porn industry and Los Angeles in April 1995, and she became her manager. Brittany appeared on 17 men's magazine covers during 1995.