A California native, Riley Steele started out working at Starbucks and at a golf course snack bar. As fate would have it, she found her big break in the form of meeting porn star Jesse Jane at a signing for the sex parody Pirates (2005) (V). Jesse advised her to enter the business, and shortly afterward Riley got a card from her. It wasn't long after that when Riley contacted Ali Joone , the director and founder of the porn production company Digital Playground. In 2008 Riley made her debut in the sequel to "Pirates", called Pirates II: Stagnetti's Revenge (2008) (V) and in 2010, along with other porn stars, she appeared in the horror-comedy Piranha 3D: For Your Consideration (2010) (V).

She got her start in the adult film industry through her meeting with porn star Jesse Jane at a signing for Jane's erotic film parody Pirates (2005) (V). Jane encouraged her to enter the business and gave her a business card.