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At the age of 12, James was first called "James Deen" due to the way he smoked. As a teenager he listened to an interview with Jenna Jameson on the nationally syndicated radio program, "Loveline." When a male caller asked Jenna how he could become a porn star. She responded that he needed to be able to masturbate in a room full of 20 of his best friends. Taking this advice to heart, James began having sex at parties and Raves. He credits this exhibitionist behavior with helping him perform in front of the camera. At the age of 17, James was attending a community college in Pasadena. While there, he decided to break into the adult film industry by meeting girls who had connections to the porn industry. Through these connections, James was introduced to Pamela Peaks who helped him choose his old nickname as his stage name (other options included Clint Cullingus). Deen was represented at that time by World Modeling. However, it was difficult for him to find work due to only being 18 and having no on-screen experience. Deen's first big break came in 2004 when Eon McKai cast him in Art School Sluts (2004). During the first year of his adult film career, James Deen worked on nearly 500 scenes.

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