Best Supporting Actor in a Comedy Series:
Jon Cryer, Two and a Half Men "Repeated Blows to His Unformed Head"
Pro: Cryer has a lot of screentime (it helps that it is a leading role masquerading as a supporting one), so that will help, along with being on the #1 sitcom.
Con: But this is without a doubt an awful performance that will surely turn-off female voters. Lusting over a pregnant Sara Rue isn't going to get him loads of votes. Those at CBS may want to see Harris win to give a boost to that show.
Kevin Dillon, Entourage "The Resurrection"
Pro: Dillon's got a good amount of screentime. After many years of being "Matt Dillon's brother," this has surely been a career-high role and performance. It's very sympathetic and if voters are looking for someone who is in need of a hug via an Emmy, Dillon's it.
Con: HBO may want to see Jeremy Piven win again. Plus he is kind of playing himself.
Neil Patrick Harris, How I Met Your Mother "Showdown"
Pro: Harris' storyline is pretty funny and it has some nice moments in it as well. It's a very showy, over-the-top role, the kind that voters have awarded in the past. His coming out this year may also score some votes.
Con: It feels like he has the least amount of screentime of the bucnh. The performance isn't as showy when compared to the likes of Piven or even Dillon. CBS may want a win for Cryer since his show is more successful. The show has it's fans, but does the Academy like it?
Jeremy Piven, Entourage "Manic Monday"
Pro: Last year's winner once again received a nod from the Golden Globes and even landed a spot at the Screen Actors Guild. It's a performance and role they have liked before and Piven gives another performance that gives him plenty of time to shine. And there is usually one performer from each genre that repeats.
Con: A split vote with Dillon, particularly from those fans who think Dillon continues to grow, while Piven's character continues to annoy. The submissions last year were a little bit weaker, so can Piven outshine this year's stronger submissions?
Rainn Wilson, The Office "The Coup"
Pro: A win for Wilson would be akin to Michael Richards winning so many times for Seinfeld. It may not be as laugh out loud funny as the others, but Wilson has screentime and the acting chops to sneak a win, particularly if the love for The Office grows.
Con: The performance might be too polarizing for voters. Plus the episode itself was not given a strong positive reaction at the earlier Emmy panels.
This is one of the more interesting races of the night. Jon Cryer is likely the only nominee who will not win. The other four are much closer than I originally thought. I think Neil Patrick Harris might suffer from being on a little-seen show, while Kevin Dillon will be hurt by Jeremy Piven more than Piven being hurt by Dillon. Rainn Wilson could rise above if the love for The Office is there and if the HBO and CBS voting blocks split. But I think we're going to see Jeremy Piven get a repeat win here. Any of the four should be considered a worthy victor, since those four have some of the better submissions of the year.
1. Jeremy Piven
2. Rainn Wilson
3. Neil Patrick Harris
4. Kevin Dillon
5. Jon Cryer