- Crosses the Line Twice: Many sketches, such as the "Nigga Please" cereal commercial.
- "Funny Aneurysm" Moment: The spoof PSA "How to Not Get Your Ass Beat 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.
- Hilarious in Hindsight: 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.
- Either this or "Funny Aneurysm" Moment, 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, Bill Cosby was finally sent to prison, at the age of 81.
YMMV / The Chris Rock Show