Will Win - The Colbert Report
Could Win - The Daily Show with Jon Stewart or The Late Show with David Letterman, or Last Week Tonight with John Oliver
Should Win - Late Show with David Letterman
Commentary - The Colbert Report has won this two years in a row, and history as of late in this category favors the old favorite. But there are three shows that could make a splash here. The first is, of course, The Daily Show. As this show is ending, there is a lot of love out there for the type of commentary that really Stewart pioneered, and they did reward it like 46 years in a row up until the last two years. There is Last Week Tonight with John Oliver, the upstart program that feels like the natural Emmy successor to the likes of The Daily Show and The Colbert Report. Then there is the legend himself David Letterman. I wasn't even sure he could get back into this race, as he had been absent for so long. But now that he is back in, I hope that voters give him one last shot at Emmy glory, one last chance to take the stage. I know the same could technically be said of Jon Stewart, but he has plenty of Emmys. Dave hasn't won an Emmy in 21 years. It is time they get him back on that stage. And honestly, while I'm not predicting it, I could definitely see it happening.