According to Deen, performing in pornographic films was his ambition since he was in kindergarten. After entering the pornography industry in 2004, he initially worked with older female performers. In 2009, he was named the "Male Performer of the Year" by AVN at the age of 22, making him the youngest actor to have won this award. Deen has a fan-following among teenage girls, a demographic that is typically not associated with the pornographic industry. In February 2012, ABC Nightline aired the feature Porn's Boy Next Door, which included interviews with both Deen and his fans. One fan described him as "the Ryan Gosling of porn".