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  • Awesome Music:
    • Dave being a huge hip-hop aficionado had the best of the best on his show. Of note is Mos Def's interpretation of "Close" while riding shotgun with Dave, Wyclef Jean's acoustic version of "President", and Snoop Dogg riffing with Tyrone Biggums with the puppets of Kneehigh Park.
    • In lieu of a musical guest at the end of the episode that featured the "White People Can't Dance" sketch, Dave showed an outtake of a jam session he had with John Mayer, Questlove, and keyboardist John Sanchez, where they performed the theme songs to Diff'rent Strokes, The Facts of Life, and, during the credits, The Jeffersons.
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  • Crazy Awesome: Rick James as played by Dave Chappelle.
  • Crosses the Line Twice: Dave's own son abandoning him, and adopting Nick Cannon as his "new daddy."
    • Even though the "Time Haters" sketch didn't air, 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.
      • Even the part where Silky shoots the master has a darkly humorous line:
        Silky Johnson: (after delivering a "The Reason You Suck" Speech to the slave master) —But the point is, is that in the future, all black people are gonna be free!!
        Slave: When's we gonna be free?
        Silky Johnson: That is a good question, my man! (thinks for a beat) How about now-ish? *BANG!!*
  • 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.
    • Before that outburst, Dave was taking it a little easier, to the point of putting a hilarious bit about it into one of his stand-up specials.
      Chappelle: I went to Disneyland... and even Mickey Mouse did it! [Mickey voice] "I'm Rick James bitch! Ha-HA!"
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  • "Funny Aneurysm" Moment:
    • In the aftermath of Chappelle's fallout with the show, a lot of humorous but still envelope-pushing moments take on this tone.
      • 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 really was killing him inside.
      • 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.
    • The "Real Movies" sketch of Deep Impact had the black president played by Chappelle hold up a newspaper with the headline "Asteroid Coming... Black President's Fault". In 2013, after an asteroid passed over Russia, Fox News supposedly speculated that President Obama, the first black president, made it happen as a plot to prove that global warming is real, though it turned out to be a hoax.
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    • One sketch includes Dave buying a camera that sees into the future, one scene show Carson Daly still hosting Total Request Live on MTV in 2013. In real life, TRL ended in 2007, four years after the episode aired.
    • In the same scene, Dave, in 2013, gives a shout-out to Justin Timberlake, reminiscing about Star Search 1992 and remembering Ed McMahon, who actually died in June 2009.
    • The "Playa Haters' Ball" sketch introduces Pit Bull with the tag "Most likely to gain weight and die." The man who played him, Patrice O'Neal, died several years later from a stroke caused by his obesity.
  • 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.
  • 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.
    Dave: "Tough break, nigga. There's always FUBU!"
    • The DJs behind this prank call must not have watched the "Zapped" sketch's second segment. Otherwise, this little mishap might have been avoided.
    • The "Love Contract" sketch involves Dave getting a sexual partner to sign a consent form to show that they're a willing participant. Some time later, California and New York introduced the controversial "yes means yes" policies for universities, where people having sex are instructed to confirm that they have a partner's "enthusiastic consent"note . Many critics snarked that the only real way to prove this was to have both people sign a consent form.
    • The R. Kelly parody, after his pee tape was later revealed to be very, very far from being his worst offense.
  • 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.
    • The skit featuring Clayton Bigsby, black white-supremacist (who was blind his whole life and was never told he was black by anyone). Cue some whack-job trying to create an all-white enclave somewhere in North Dakota discovering the truth about his own ancestry...
    • One of Chappelle's skits involved his character shooting a white slave owner, and when everybody subsequently groaned at the joke, Chappelle quipped "Apparently shooting a slave master is only funny to me and Neal." Turns out, it was also funny to a man named Quentin Tarantino, whose Django Unchained took the whole concept of "black man guns down white slave owners" (albeit a former slave on a Roaring Rampage of Revenge instead of a time-travelling playa-hater like Silky Johnson), and, even though it got its OWN share of controversy after coming out, it became a commercial and critical success, for not only being absolutely hysterical, but also being awesomely cathartic.
    • What Men Want is now a real movie that released in 2019.
    • In 2003, audiences laughed at a skit that had the History Channel covering street gang wars. In 2007, along came Gangland.
  • Memetic Mutation:
    • Rick James, Sam Jackson beer, Wayne Brady's bitch-choking, "cocaine is a hell of a drug", "game... blouses", etc., etc.
    • "Modern problems requires modern solutions."
  • 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 way too excited by hearing the n-word a lot.
  • Retroactive Recognition: Numerous examples; the two most notable are probably Bill Burr and Rashida Jones.

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