Join Miss May 1998 Deanna Brooks as she takes you through some of the best moments when celebrities and playmates meet. See William Shatner Rob Schnieder Flava Flav Joe Don Rooney Pharrell Williams and Jenny McCarthy get behind the lens to test their skills with some of the world's most beautiful women including Playmate of the Year 2005 Tiffany Fallon.
Four hot celebrities, on the dream assignment of a lifetime, find that being on the other side of the lens can be a very exciting position. Dale Earnhardt, Jr., teams up with Playmate Triplets Erica, Nicole and Jaclyn Dahm for a high-octane photo shoot. Model, actress and three-time Playboy covergirl Carmen Electra steps behind the camera and teaches Playmate Jennifer Walcott a few new things about striking a pose. Howard Stern funny man Artie Lange hams it up behind the lens with Playmate Lindsey Vuolo. Wrestling star Jerry "The King" Lawler meets his match with Playboy.com Cyber Girl Wendy Culp.