When an awards show kicks off with a huge upset, the rules go out the window. The Emmys have always been pretty tough to call, but with two massively successful, critically ballyhooed series in the comedy and drama categories (30 Rock and Mad Men, of course), this year's awards could have looked like a repeat. They did, to an extent, when 30 Rock and Mad Men swept the final big awards again. But the night was also full of upsets, pleasant surprises, and downright jaw-droppers in some of the other major categories. Here are the five biggest shockers:

1. Kristin Chenoweth Wins Best Supporting Actress in a Comedy

The first award handed out was the first OMG moment of the night. Chenoweth was up against Jane Krakowski from 30 Rock, Amy Poehler and Kristin Wiig from SNL. Her show was canceled, and yet, there she was at the podium. Poehler seemed like the frontrunner going in (especially after her now-classic performance as Hillary Clinton), but Chenoweth was certainly charming in the sadly short-lived Pushing Daisies. And her chirpy-yet-emotional acceptance speech was among the most entertaining of the night.

2. Jon Cryer wins Best Supporting Actor in a Comedy

There were two 30 Rock actors in the category, Tracy Morgan and Jack McBrayer, and it's very possible that they split votes between them. But if it wasn't going to be one of the Rock stars, I would have expected Rainn Wilson from The Office or Neil Patrick Harris, who did a terrific job as host and would have made for a delightful television moment. But if there was a dark horse in the category, it was Cryer, who was on his fourth nomination with no Emmy love until tonight. This was a huge surprise.

3. Toni Collette Wins Best Actress in a Comedy

I predicted this one, and was still shocked to actually see it happen. Tina Fey had a dream career year playing Sarah Palin on SNL and watching 30 Rock surge slightly in the ratings, and even though Collette turned out a stunning performance as a woman with multiple personalities, I wouldn't have been surprised to see Fey take it all the same. This one goes into the pleasant-surprise category. Fey won last year, after all, and won in another category this year (for her SNL guest appearance).

4. Michael Emerson Wins Best Supporting Actor in a Drama

As much as I love Emerson's performance on Lost, I thought next year would be his year to take the big prize following the show's final season. This year, I expected John Slattery to win for his performance in the Emmy darling Mad Men, or if not Slattery, Aaron Paul for Breaking Bad. But Emerson is certainly deserving.

5. Cherry Jones Wins Best Supporting Actress in a Drama

It's always a shock when a performance that no one talks about on a series that no one talks about (anymore) takes home an award. Granted, when it was first announced that Jones was joining 24 as the show's first female president, it was a big deal. But it was yet another wobbly season for the show creatively, so I was surprised to see Jones even nominated. I expected a win for Hope Davis's brave performance in In Treatment, perhaps her costar Dianne Wiest, or one of the Grey's ladies (Sandra Oh and Chandra Wilson).