* CrossesTheLineTwice: 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..."
* GrowingTheBeard: Literally and figuratively. His [[https://www.youtube.com/watch?v=0O2fNO2AZyU&feature=related early stand-up]] when he was young and cleanshaven was mostly absurdist and less personal. In a podcast interview with fellow comedian Creator/MarcMaron, he says his stand-up began to change after he got married and had kids, and his material began reflecting his real life.
* HarsherInHindsight:
** His previous routines included shockingly frank discussions of the various dislikes he has of his marriage. Most listeners just filed this under "RuleOfFunny", 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. [[WhatWereYouThinking Wonder why]]?
** After the news came out that Louis has masturbated in front of numerous unwilling women in the industry, many of his jokes relating to perversion and his habits seem less harmless than they once did. For instance:
--->"One time I was at school, and I was volunteering at recess. It's something that you do if you're a good parent, about once a month you go to school, and you just stand there, and you watch recess, masturbate, whatever you wanna do."
* HilariousInHindsight: Potentially it's both this trope and [[HarsherInHindsight the inverse]], but he had a bit describing the KarmaHoudiniWarranty for white men.
-->'''Louis''': We're gonna pay hard for this shit, you gotta know that. We're not gonna just fall from #1 to 2, they're gonna hold us down and fuck us in the ass forever, and we totally deserve it. But, for now, WHEEEEEEE!
* OvershadowedByControversy: The above mentioned sexual harassment allegations in November 2017 did a significant amount of damage to his reputation, but leaked audio from a stand-up set in December 2018, featuring him making jokes at the expense of transgender people and the 2018 Parkland shooting victims, pretty much destroyed it altogether.
** His career seems to have slowly recovered after his 2020 special ''Sincerely Louis C.K.'' was released to mostly positive reviews and won a Grammy for Best Comedy Album in 2022. Time will tell if the public will be ready to give him a chance at [[CareerResurrection a full career comeback]].
* TearJerker: Louis C.K. was invited to deliver the final speech at a star-studded tribute to Creator/GeorgeCarlin in March 2010. In it, he describes the impact Carlin has had on his career and life, and even though it starts off rather funny, his own emotional distress becomes more and more obvious towards the end. What drives it home, however, is when he apologizes to the audience for [[SadClown not being able to close funny even though he is supposed to]] before bidding farewell.
----