Entourage should simply be happy someone even still watches it. What was once a great and inventive show is now boring and unintelligent, and I don't think it has a shot in hell of winning this category.
Flight of the Conchords is quirky and weird, which may give it a nice minority of voters who enjoy shows like that. However I feel that most of the voters will look right over it for the more popular offerings.
Weeds finally made it into the final cut, and I am very happy about it. However, it took them so long to get into the category, that I feel it may not be as popular as we think.
How I Met Your Mother is a great show, and one of the few sitcoms remaining on TV. Despite the ratings, and the NPH love within the Academy, I don't think it will be enough for this first time nominee, but don't count it out.
Even when it's not acutally on TV, Family Guy tends to stir up controversy wherever it goes. Being the first animated series in over 50 years to get nominated for the top prize is a huge deal, and despite the Bill O'Reillys of the world who hate this show (personally I think he should shove it), it does have a broad popular base, and its campaign strategy has been unusual and effective. History might happen come Emmy night, just wait and see.
The Office is now considered the bridesmaid in this race. While I thought it submitted well, I still think that the power of another particular NBC show is too much for this one to handle.
This brings me to the Juggernaut of them all: 30 Rock. Despite a tough category this year, I think the popularity and favoritism for this show means the streak isn't over yet.