Emmy Race 2009: The Biggest Surprises

Mad Men's John Hamm versus Gossip Girl's Chace Crawford? You bet your ballot! It's Emmy season, which means any primetime actor is entitled to submit his or her name for consideration. The result is a comically mismatched list of men and women vying for best-actor/actress nominations. Crawford — along with costars Ed Westwick and Leighton Meester — will compete against The Shield's Michael Chiklis and Damages' Glenn Close for nods in the top drama acting categories. (Penn Badgley and Blake Lively steered clear of the competition altogether.) And talk about moxie: Disney Channel's Selena Gomez and Miley Cyrus decided to take on reigning champ Tina Fey in the best comedy actress race. (The six finalists in each category will be announced July 16.) But not everybody craves a berth in a top field: For the first time, Grey's Anatomy's Patrick Dempsey entered himself in the supporting category, where he'll duke it out with Justin Chambers and T.R. Knight. Why? ''Grey's is not about one person,'' says his rep. ''It's an ensemble.'' Better not say that around Ellen Pompeo, who — as in years past — is in contention for best actress.