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Simpson responded to Arizona advertisements for nude models, and was first featured in photos on the Amateur Allure web site, performing oral sex, then on her own web site, under the name Cory Heart. She picked Courtney Simpson for her primary stage name based on her own first name, and the last name of singer Jessica Simpson.
On December 2, 2005, The Arizona Republic reported that Arizona State University officials were looking into any legal claims they might have in relation to a possible infringement of trademarks and intellectual property over Simpson performing in an ASU cheerleader uniform in the pornographic video Gina Lynn's Double Dutch. The film's producer, Gina Lynn, ultimately decided to reverse the uniform on the video's box cover so the initials said "USA" and not "ASU", and also to blur out the uniform during the time Simpson wears it on-screen. Simpson continued shooting films during the controversy, working five to six days per week.