I don’t want to speak ill of the recently TV departed so I’ll let the boss do it for me. As Dustin says in his incredibly touching piece about the origins of this site, “David Letterman was an asshole.” But he was a lovable asshole. He was an asshole that you wanted to hang out with even if sometimes he turned his assholery against you. Because everyone seemed to know it was just part of the joke. And now that he’s gone, who will take up that mantle?
Let’s look at the Big Five currently on air (Sorry, Colbert. But let’s get real, you were never going to win this. You aren’t actually an asshole, you just play one on TV.): Jimmy Fallon, Jimmy Kimmel, James Corden, Seth Meyers, and Conan O’Brien.
Corden and Fallon are gone right away. Meyers has a certain asshole-iness to him, but never mistake playfully smug for asshole. “Smug” acts like he wants you to like him, “asshole” knows you’ll like him more if he pretends he doesn’t care about it.
So that leaves Kimmel and Conan. Both make strong cases, but only one goes above and beyond. Kimmel’s ongoing prank wars seems like it should put him ahead, but it actually proves he’s not that big of an asshole. No one intentionally engages in asshole behavior with actual assholes. Sorry, Kimmel, but it seems your bromance with Krasinski is your undoing.
But don’t think for a second that Conan wins by default. Underneath the self- deprecation, Conan is the best kind of lovable asshole. The kind that you want to be around even when they’re clearly being an asshole. The kind that makes you laugh even when you’re the butt of the joke. The kind that would do this:
Conan’s the kind of asshole who might jump on an employee in the hallway and choke him, but he wants to know how that employee feels about being choked. He’ll also imply that the choking is a sexual release thereby sexually harassing an employee during a performance review. He’ll ask his employees which one of their co-workers should be fired, and then tell the chose employee that his co-workers all want him fired. But he’ll make everyone laugh while he’s doing it. And that’s why he’s the King of the Late Night Assholes.