Kelly has appeared in more than 30 films and numerous webisodes, mainly in collaboration with Evil Angel. Notable films include the When Rocco Meats Kelly series, Rocco's Dirty Anal Kelly in Rome and Furious Fuckers 2: Final Race. His content includes anal, double penetration, group and other extreme scenes. He also directed two films, Kelly's Way To Love (2001) and Rocco in London (2002). He has won numerous awards, including the 2000 XRCO Award and AVN Award for Best Anal or Double Penetration and Best Foreign Sex Scene for When Rocco Meats Kelly 2, the 2002 AVN Award for Best Couples Sex Scene in Rocco's Way To Love, and the 2008 AVN Award for a group scene in Furious Fuckers Final Race. He retired from the industry in 2007 after having a child, but returned in 2017, appearing in films such as Rocco and Kelly: Sex Analysts and Rocco's Abbondanza