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In no particular order, this is my favs from 2010 - 2020.
Anthony Jeselnik - a master of not apologizing and leaning as hard as possible into the shock niche better than anyone else while not being a weeny about like most other “shock jocks”
Tig Notaro - particularly her album about her breast cancer, she masterfully guides your own empathy working against how utterly hilarious her jokes are about almost dying
Hannibal Burress - a completely different take on dry humor which is largely dominated by the Brits, he is monotone, seemingly sarcastic, and the wit is endless. I almost wonder if he is a pioneer in a new version of American dry humor that you can start to see popping up elsewhere like with Sam Morril