I recently saw Louis C.K. in concert for the first time, and I loved it. As he's grown into fatherhood and early middle age (he's now 45), he's continued to break ground by running away from the absurdist comedy he started with and toward the awkward, bracing confessional style he's perfected on specials like Chewed Up and Hilarious and his eponymous FX series. It's not that he never did observational stuff before, though (his bit about being broke remains a classic), nor has he totally given up on more fanciful lines of thought (his latest hour includes a discourse on what would happen if a tuna and shark were friends). He's just better than ever at living in the tension between the two, and mixing them perfectly.
He's defined by those kinds of seemingly contradictory but ultimately pleasing splits, too. His rant on "Late Night With Conan O'Brien" from 2008 went viral under the title "Everything's Amazing and Nobody's Happy." and it spoke directly to the fact that we live in the most technologically advanced period to date yet we're constantly annoyed with the things we've invented. This is the heart of Louis C.K.'s comedy, and one of the best examples of the way he reconciles seemingly discordant ideas into one complex worldview. It's not that he thinks technology is bad, or that everyone is awful. It's that the truth is somewhere in the middle.
He closed his set with an encore riffing on such contradictory ideas, introducing each joke with an "Of course ..." / "... but maybe" set-up. The goal was partly to see how far he could go, and to continue pushing the boundaries he loves to eradicate with his comedy. But it was also a great way to underscore how much he sees the world in shades of gray, and how sometimes the best answer to a multiple-choice question is "all of the above." For instance, one of the jokes (and I'm going to paraphrase pretty loosely here) talked about how of course it's bad that some people have nut allergies, but maybe if you have a nut allergy, you're too weak to live in the first place. Or: of course it's bad that U.S. troops come back from war wounded, but maybe they and we shouldn't be surprised because, after all, they were shooting, too. Louis C.K. is one of the best comics working today not just because he's funny, but because of how he's funny. He uses humor to glue together things that shouldn't fit, and he makes it work.