Jon Cryer, "Two and a Half Men"

Nomination Status: Supporting Actor favorite makes the leap. The love should carry over.

In His Favor: Cryer has been nominated six straight years for Supporting Actor in a Comedy and correctly decided this was the right year to jump to Lead. In the successful transitional season for his hit CBS comedy, Cryer's Alan got to mourn the death of his brother and have a heart attack and the "Pretty in Pink" star committed gamely to those moments of semi-drama in a way that voters are likely to respect.

Working Against Him: If he were still in Supporting, Cryer would have been a lock, so it's a risky move to shift categories and it's a move that only occasionally works out. Is it completely possible that Cryer could slip right through the cracks this year? Yup. I just think there's enough affection for him that he'll stick around.