%% "The Dreamer" was released 31 Dec 2023 and No Recent Examples rules may apply to some tropes for that special. Please check before adding them to this page.

* AwesomeEgo: His ''Equanimity'' special has a bit about this, PlayedForLaughs. Dave boasts that he’s so good at standup that he can write jokes in reverse, to the point where he can pick a random punchline out of a jar and make it hysterically funny. He pulls it off twice in the night. The punchline? [[spoiler:"So I kicked her in the pussy."]]
* CriticalDissonance: On Website/RottenTomatoes, two of his Creator/{{Netflix}} specials, ''Sticks and Stones'' and ''The Closer'', were polarizing among critics for their PoliticalCorrectnessIsEvil stance (most notably gender identity politics), but had plenty of fans among audiences.
* HilariousInHindsight:
** Dave's bit on [[Series/SesameStreet Oscar the Grouch]] being profiled/discriminated against, decades later, would be thematically revisited in a ''Film/{{Joker|2019}}''-[[https://www.youtube.com/watch?v=kqpak5lFxvs inspired parody]] by ''Series/SaturdayNightLive''.
** Dave accurately predicted that Creator/TheHistoryChannel would cover [[Series/GangLand gang wars]].
* MisaimedFandom: Candace Owens, a conservative black reporter, expressed admiration for Chappelle's opposition to political correctness in anticipation of his first 2020 special ''8:46''. However, this special was explicitly left-leaning (Chappelle has supported Democrat nominees in the past) and supportive of the UsefulNotes/BlackLivesMatter movement, thus proving Owens' and Chappelle's politics do not align too much. Like Creator/BillMaher, he has since picked up a PeripheryDemographic of right-leaning fans who are well aware that Dave is not explicitly conservative himself, but nevertheless respect him for standing up on issues like cancel culture and being willing to call out what they both see as extremist behavior on his own side.
* OvershadowedByControversy: Discussions about his 2021 special ''The Closer'' are likely to center around its inclusion of jokes about the LGBTQ+ community (in particular transgender people) and Chappelle expressing support for Creator/JKRowling amid accusations of transphobia, which led to strong criticism from LGBTQ+ people and allies.
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