Jessica Drake spent much of her early life growing up around the state of Texas in different cities including San Antonio and El Paso. While majoring in psychology at a college in El Paso, Jessica took a job as a house dancer at a local strip club. Through an agency, she later applied to be feature dancer at another club nearby, and here she met adult film director Michael Raven, who was photographing a contest. Raven and his wife Sydnee Steele gradually introduced her to the porn industry. Jessica Drake began by posing for magazines and appearing on Playboy TV, and was later taken to a film set, where she was the "condom and lube girl" for a scene starring Jill Kelly and Mark Davis.
In 1999, she made the decision to become an adult film actress and shot her first movie, which was directed by Raven. She signed a contract with the studio Sin City early in her career, but left the company after about a year and a half as "things did not work out." She gained her first AVN Award in 2001, winning "Best Tease Performance" for her role in VCA Pictures' Shayla's Web. In 2003, she signed an exclusive contract with Wicked Pictures, after turning down offers from other companies. Her performance in Fluff and Fold, a romantic comedy set around a laundromat, earned her the 2005 AVN Award for "Best Actress, Video" and the 2005 XRCO Award for "Single Performance, Actress." She won "Best Actress, Film" for her role in Manhunters, for which Drake trained as a bounty hunter during pre-production. Her directorial debut came in the 2008 film What Girls Like, having gained previous experience working as Brad Armstrong’s assistant director on titles such as 2007's Coming Home. In January 2009, she won her third "Best Actress" AVN Award, this time for her performance in Fallen, which she has described as "the best movie I have ever been in." At the 2010 AVN Awards, Drake was inducted into the AVN Hall of Fame.