Louis CK/YMMV

Acceptable Targets: Averted. All targets are acceptable to him. Louis C.K. doesn't just throw political correctness to the wind - he holds it down and fucks it right in the face.
Crosses the Line Twice: Frequently, he'll make an offensive joke, back away from it a bit, and then make an even more offensive joke on the same topic.

"...I'm not condoning rape, obviously. You should never rape anyone. [pause] Unless you have a reason, like you want to fuck somebody and they won't let you..."

Funny Aneurysm Moment: His previous routines included shockingly frank discussions of the various dislikes he has of his marriage. Most listeners just filed this under "Rule of Funny", assuming that his wife was okay with this because maybe it was all fake, or she understood that it's just for the joke and not serious. Then we find out on his next special that his wife divorced him. Wonder why?
Growing the Beard: Literally and figuratively. His early stand up when he was young and cleanshaven was mostly absurdist and less personal. In a podcast interview with fellow Marc Maron, he says his stand up began to change after he got married and had kids, and his material began reflecting his real life.
Some Anvils Need to Be Dropped: During Hilarious, he brings how everyone wants us to Think of the Children and yet many parents put minimal effort into how they raise their kids. Also a Crowning Moment of Awesome.