The third season of Mad Men debuts this Sunday, August 16, on AMC. The show's relevance outdistances its actual ratings, especially in the media and advertising worlds in which the show is set. The 60s-era shenanigans of Don Draper, Roger Sterling, and their compatriots is rivaled only by the gossipy fun every Monday morning rehashing their actions—and thinking about how today's ad-industry characters stack up with Madison Avenue fiction. We play "Who Would Play?" with a real-world cast of creative directors and ad magnates.