Biggest Emmy Award Upsets of the Past 25 Years

From whacked Sopranos to spoiled Hamms, the award show's most shocking wins and surprising losses

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Pretty much every acting category, 2007

Did The Sopranos' final cut to black short-circuit Emmy voters' brains? All we know is that the awards doled out during the year of the seismic mob drama's last half-season made for the most upset-ridden slate in the history of the show. James Gandolfini wrapped up his run as Tony Soprano, one of the single best performances in the history of television, by getting stiffed in favor of James Spader in yet another David E. Kelley joint, Boston Legal. Carmela fared no better, with Edie Falco losing to Sally Field from Brothers & Sisters. And Katherine Heigl was left speechless — literally, as she thought her chances of winning were so slim she didn’t bother preparing one — by her Best Supporting Actress victory over not only The Sopranos' Aida Turturro and Lorraine Bracco, but also her own Grey's Anatomy costars Chandra Wilson and Sandra Oh.

The comedy categories were just as crazy. Ricky Gervais oozed his way to the top of the Best Actor heap for his leading role in Extras over heavy-hitters Alec Baldwin (30 Rock), Steve Carell (The Office), Charlie Sheen (Two and a Half Men), and Monk's Tony Shalhoub from Monk, who was gunning for a threepeat at the time. And while few people were genuinely "upset" when the endearing America Ferrera from Ugly Betty bested a field of accomplished comedy veterans comprising Tina Fey (30 Rock), Julia Louis-Dreyfus (The New Adventures of Old Christine), Felicity Huffman (Desperate Housewives), and Mary-Louise Parker (Weeds), they sure were surprised. Seriously, what the hell happened this year?

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