These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Even though the "Time Haters" sketch didn't air (see Dude, Not Funny! for why), most of the buildup before hand was pretty damn hysterical: First, the Time Haters deliver a No-Holds-Barred Beatdown to Adolf Hitler, and even the parts on the slave ranch before Silky shoots the slave master (up to calling the master a 'cracker' and 'honky', and then holding him at gunpoint) were pretty funny too.
Discredited Meme: Dave actually chewed out fans at a concert for endlessly repeating the Rick James line.
Chappelle: "You know why my show is good? Because the network officials say you're not smart enough to get what I'm doing, and every day I fight for you. I tell them how smart you are. Turns out, I was wrong. You people are stupid."
Dude, Not Funny!: At the end of the Time Haters sketch, one of the sketches featured in an episode on sketches that weren't fit to air, Dave's hater persona, Silky Johnson, goes back in time to slavery times and shoots a slave master. Dave warned that the moment brought the skit to a screeching halt and predicted it would bring the episode to a screeching halt. The audience did indeed groan, but they laughed when Dave said, "Apparently shooting a slave master is only funny to me and Neil. If I could, I would do it every episode."
This was also one of the things that led to his Creator Breakdown by way of the "racial pixie" skit, which involved characters of various races being egged on by said pixies to act out the stereotypes of their races. In this case, the black pixie was an unbelievably offensive Stepin Fetchit-style darky archetype; Chappelle was already on the fence about the skit to begin with, but when a crew member laughed in a way that he felt was aimed at him rather than with him, he was downright disturbed by it and began to seriously question whether he was turning into what he had originally been lampooning.
Ear Worm: Haters wanna hate/Lovers wanna love/I don't even want/None of the above/I want to piss on you!
"Funny Aneurysm" Moment: During the "Niggar Family" skit, Chappelle's character follows up a collection of n-word puns by saying in a humorous tone, "This racism is killing me inside." After his existential-angst-fueled trip to Africa brought on by the racism of his show, it's hard to laugh at that line, because that racism was killing him inside.
In the aftermath of Chappelle's fallout with the show, a lot of humorous but still envelope-pushing moments take on this tone.
The Wayne Brady episode gives us an intro of Dave quitting over negotiations for the third season, this line especially stands out following the "Lost Episodes" run:
Network Official: Suit yourself Dave, you've already shot all your sketches. At this point in the season you're replaceable.
Growing the Beard: The first season was largely ignored until around episode eight, when two sketches aired that basically caught the public's attention: The first was an R. Kelly parody, which had Dave as R. Kelly singing a song making fun of the singer's sexual fetish of urinating on women. The second was a Real World parody, where Dave made fun of the white people to black people ratio of the show by imagining what would happen if MTV would cast an edition of the show where there was one white guy (comic Christian Finnegan) and the rest of the cast were crazy black people, who mercilessly torment the sole white guy.
Guilty Pleasures: Of a sort. The show is intelligently written and well-acted, but it can be very uncomfortable for white fans to realize what they're laughing at.
Harsher in Hindsight: During the "Racial Draft" sketch, Tiger Woods becomes fully black. After clamoring about how he'll be going from eating fried rice to eating fried chicken and getting the chance to say "Fo'shizzle", the commentators receive word that he's lost all of his endorsements. After his later stint as a man who's cheated on his wife with an astronomical number of women and his falling out with the media and some of the people who admired him, Tiger Woods has lost most of his endorsements, to the point that his appearance at the Masters had him with his own logo. Your sympathies towards the man are subjective, of course.
Hilarious in Hindsight: The point of the Lost Episodes' "New 2Pac Song" sketch, which pokes fun at "2Pac Lives!" conspiracy theorists.
Also the unaired Daddy Day Care sketch became a lot funnier when Daddy Day Camp came out the following year.
People watching the show now may not even realize that the actual show Trading Spouses did not yet exist when the sketch with that name was created. It was actually a spoof of the show's less uncomfortable forerunner Trading Spaces.
Misaimed Fandom: One of the factors in Dave Chappelle's Creator Backlash was the realization that a significant chunk of his audience was racist white people taking the racial stereotyping at face value and/or just being titillated by hearing the word "nigger" a lot.