Jane read an article on Tera Patrick that said that Patrick worked for adult-film production company Digital Playground. She contacted them and was quickly signed to a contract. Her first scene was with Devon in No Limits. Within months of winning the contract, she appeared on Showtime Network’s Family Business, where she was filmed at the Adult Video News awards show and convention. Jane appeared on the cover of Texas-based metal band Drowning Pool’s second album Desensitized and was featured in the music video for the albums first hit single, “Step Up.” She has said that Drowning Pool is one of her favorite bands. On the July 25, 2006 episode of The Tonight Show with Jay Leno, during the “Jay Walking” segment, she gave her name as “Cindy” and said that she currently worked at Hooters. An adult magazine cover featuring her as Jesse Jane was then shown onscreen. In 2005, she was featured as UnRated Magazine’s Vixen, to launch the music review magazine’s new edition of Vixens. The films in which Digital Playground cast Jane, such as No Limits, Beat the Devil, and Loaded, proved popular enough to warrant her own line of sex toys, as well as secure nominations for several awards. She starred in the erotic film series ”Pirates”.
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