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1* CrossesTheLineTwice: Many sketches, such as the [[http://youtu.be/sXDFbFbNXOs "Nigga Please" cereal commercial]], which at one point shows a black customer almost beating up a white cook for mentioning the cereal's name and ends with the mention of another product called Cracker Ass Crackers.
2* HarsherInHindsight: The spoof PSA "How to Not Get Your Ass Kicked by the Police" became extremely winceworthy in 2014, when unarmed black man Eric Garner was killed by police officers. And when the officer wasn't indicted, it sparked protests nationwide. It got worse in 2020, with the murders of George Floyd and Breonna Taylor by the police.
3* HilariousInHindsight:
4** In the first episode, Chris is touring the studio as though it were years later, and one of the things he shows is a self-help video by O.J. Simpson titled ''I Didn't Kill My Wife! But If I Did, Here's How I'd Do It''. Years later, O.J. actually would publish a book entitled ''If I Did It'' about how he would've done the deed.
5** Either this or HarsherInHindsight, depending on one's sense of humor: The sketch, "True Stories of the Justice Squad", where the titular squad take forever to bust a drug-dealer, while he gets richer and richer, finally making their move on his 93d birthday, ensuring that, "He would spend the last thirteen seconds of his life in a federal penitentiary". Became one or the other when, after over forty years of drugging and raping women, Creator/BillCosby was finally sent to prison, at the age of 81.
6** Chris' phony political ad in which he plays an aspiring political candidate named Roger Sykes "who will get you all the pornography you need". Rock has admitted to a terrible pornography addiction that, in his words, utterly ruined his marriage.
7** A cold open kicking off season four with a fake news report about a growing "smacking-upside-the-head rampage" across the nation seems, after "Slapgate", almost prescient.

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