In the weeks leading up to the 2007 Primetime Emmy Awards, I'll be looking at the nominees in some major categories and trying to predict who's most likely to win in these Emmy Breakdowns. Today's category: Best Supporting Actor in a Comedy Series.

Jon Cryer ("Two and a Half Men") — As I've said before, I can't claim to be an expert on this show since I don't find it particularly entertaining and don't watch it regularly. But during the few times I have caught snippets of "Two and a Half Men," I've found Jon Cryer's performance to be much funnier and more compelling than Charlie Sheen's. He has that wry, quirky humor that was so endearing in Pretty in Pink, and I will probably always think of him as Duckie, no matter what role he's playing. In this category I don't think I'd personally choose Cryer, but I wouldn't be shocked or altogether annoyed if he took the award.
Chance of winning: Moderate to High

Kevin Dillon ("Entourage") — Watching Kevin play Johnny Drama I can't help but feel that there is a tinge of autobiography (Kevin's brother Matt being the real life Vince), which brings odd touching moments to the otherwise lighthearted show. Drama never gets the best one-liners and is definitely awkward at times, but it's great to see he's finally found a solid success plot. Kevin plays it with the right level of caution, but I don't think that this is his year for the Emmy. Even so, as "Viking Quest" era Drama would say -- VICTORY!

Chance of winning: Low

Three more nominees to go so read more

Neil Patrick Harris ("How I Met Your Mother") — Although it took me pretty much all of Season 1 of "How I Met Your Mother" to stop thinking of Neil Patrick Harris as Doogie, I am now completely over that and all I see is Barney, the epitomy of awesomeness who is fighting with all his might to hold on to the swinging single life while his two best friends are spiraling towards full on adulthood. NPH as Barney carries the show and I think after "How I Met Your Mother" was looked over for all of the other major Emmy categories, he deserves this award. Regardless of the outcome, you can be sure that Barney will...wait for it...Suit Up for Emmy night.

Chance of winning: Moderate

Jeremy Piven ("Entourage") — As the reigning king of the Supporting Actor in a Comedy Emmy and with Ari Gold nowhere close to slowing down, it would be a breeze to hand this one to Piven again. Jeremy hasn't lost his impeccable timing, either. It would be easy to give him the Emmy and easy to imagine him back up on that stage, but as someone who is growing tired of Ari's schtick, I'm sort of hoping that he won't walk away with another one.

Chance of winning: High

Rainn Wilson ("The Office") — In his time on "The Office," Rain Wilson has created a unique, hilarious and refreshing character in Dwight Schrute, providing the inspiration for dozens of "Dwightisms" and even a bobble-head doll. Part of what makes Dwight so funny is that Wilson takes him so utterly seriously — as seriously as Dwight himself takes everything in life, from his boss to his job title to his secret affair with Angela. It's not that Dwight is just a wacky character and Wilson should be recognized for that, but rather that it seems like Wilson works incredibly hard to make Dwight a real, 3-dimensional person who's simply misunderstood by his peers. Wilson would be my pick for this category, and I have a feeling I won't be alone. Chance of winning: High

Cryer and Harris photos courtesy of CBS
Wilson photo Source