Five Shocking Emmy Wins!

Taking in last 10 years of surprises, upsets and crimes from TV's biggest night

By Joal Ryan Aug 27, 2010 8:35 PMTags

Remember when that guy from Night Court won the Emmy for, like, a million years in a row? Of course not.

The memorable Emmy-winning moment is a surprise! An upset! Perhaps even—gasp!—a crime! Just like these blasts from the awards-show's past:

Oh, and before we begin our countdown, we should let you know we decided to keep our list to the Emmys' last 10 years. You know, so as to avoid having to Google that guy from Night Court's name. OK, here we go…

1. People Actually Watch Arrested Development?! Sure, critics watched—and loved—the Bluths, but critics are hardly people. So, how could Emmy watchers be sure that Emmy voters had tuned in? They couldn't. Which made the show's 2004 Comedy Series win all the more surprising. And record-setting. At the time, Arrested was the lowest-rated broadcast network comedy to win the comedy Emmy.

2. James Spader Crosses Up Tony Soprano?! At the 2007 Emmys, the jukebox playing The Sopranos' swan song abruptly cut off when Boston Legal's chief legal eagle unexpectedly made a spectator of James Gandolfini in the Lead Actor in a Drama Series race. Said a flummoxed Spader: "I feel like I just stole a pile of money from the mob."  

3. Everybody Loves Desperate Housewives Everybody Loves Raymond?! Once upon a time, Desperate Housewives was as hot as Eva Longoria Parker's film career used to be. So, in 2005, when the then-sensation picked up 15 nominations (as many as Will & Grace!), and proceeded to win for directing and acting (Felicity Huffman and Kathryn Joosten), it seemed prime to wrap things up in the Comedy Series category. But then Everybody Loves Raymond, which was over, done and could no longer promote the network cause (and had previously won, to boot), took an unexpected victory lap. Housewives hasn't been a major contender since.

4. Cable Really Counts?! Going into the 2001 Emmys, Sex and the City was like most cable shows of the time, save The Sopranos: an Emmy loser. The big night didn't change anything. The HBO phenom, up for 10 Emmys, whiffed its first nine categories. Then, out of nowhere, it beat free-TV's finest to claim Comedy Series, become the first cable show, comedy or drama, to win the top prize, and prove once and for all the CableACE was obsolete.

5. The Amazing Race Is More Amazing Than Ruben and Clay?! After winning even more consecutive Emmys than the Night Court guy (OK, yes, the great John Larroquette, and, no, we didn't have to look him up), it's hard to recall when The Amazing Race was not considered a shoe-in for Reality-Competition Program. But in the first year of the category, in 2003, The Amazing Race just didn't seem like it had the juice to squeeze out American Idol, hot from its Ruben Studdard-Clay Aiken mega-rated finale, or reality granddaddy Survivor. But it did. And it has. And no one's shocked anymore.