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.

Don Draper's colleagues and rivals at Sterling Cooper are alternately idolizing him and plotting to topple him. BBDO North America chief creative officer David Lubars may or may not have knives targeted at his back in-house, but the hype that surrounds him as the new-media creative genius who will drag Madison Avenue into the 21st century has plenty of rivals itching for that industry sage mantle. And like any creative auteur at the top, when he isn't actually dreaming up the work, he still gets to take credit for it (Remember Cannes 2008, HBO Voyeur anyone?).

Sir Martin Sorrell may not have the weak heart of Roger Sterling when it comes to arteries or women, but he certainly has the same ruthless love of numbers. WPP Group started as a shopping-basket manufacturer, until CEO Sorrell stormed the ad industry with a few hostile takeovers, a vicious temper, and arguably the largest incentive package in British corporate history to create the second largest ad company in the world.

Queens-bred Donny Deutsch might not have had the WASPY upbringing of enfant terrible Pete Campbell, but he certainly has the same daddy issues as the ambitious account exec. After Deutsch's father, David, fired little Donny from his own agency, junior came back for round two, this time reincarnated as a creative guy (who would later reincarnate himself again as a media personality) who cashed out for $265 million. Take notes, Pete.

Peggy broke through the secretarial wall only to get typecast as the genius jingle-writer for all things female (Belle Jolie lipstick and the racy "Rejuvenator"). Forty years later, Young & Rubicam global director of creative content Kerry Keenan wants to make sure the same pigeonholing doesn't happen to her. "I was worried about being viewed as a girl running a girl's account like makeup, stockings, or tampons," Keenen recently told Advertising Age regarding her initial strategy when she started in adland. Now one of the few female creative heads in the industry, the subtext of her comments still depressingly reads, "boy's club."

As much as Duck Phillips--who botched his surreptitious Sterling Cooper merger--will never be a Roger Sterling, MDC Partners CEO Miles Nadal will never be a Sir Martin Sorrell. Despite the yacht-riding, Bahamas-residing Canadian's wild fantasies of becoming an eccentric ad conglomerate magnate, Nadal hasn't managed one savvy chess move since acquiring Crispin Porter + Bogusky in 2001.

Ken Cosgrove managed to get a byline in The Atlantic Monthly with his short story "Tapping a Maple on a Cold Vermont Morning," but Toby Barlow has one literary step up on him. Last year Barlow, JWT Detroit's Executive Creative Director, published his first novel Sharp Teeth entirely in free verse, which according to Publishers Weekly is a "gut-wrenching, sexy debut, a horror thriller in verse, follows three packs of feral dogs in East L.A." More fun than hawking for Ford, eh Toby?

If Italian immigrants like art director Salvatore Romano were the burgeoning creative class of the 1950's, then the Scandinavians taking over Madison Avenue are their digital-age counterparts. After tearing up the interactive scene over at AKQA for the past few years, Denmark native Lars Bastholm recently moved to Ogilvy North America, where he now reigns as its chief digital creative officer.

Faris Yakob's fraying crown of brown curls may lack the polish of Harry Crane's slicked-backed do, but both are media mavericks of their time. Crane pioneered the agency's new television department, while Yakob, McCann Erickson's Chief Technologist, made his name as a rogue communications planner at Naked Communications.