One of the shows that I miss to this day that’s no longer on the air is, Chappelle’s Show. Even though it had a short run (2 seasons, if you include the “Lost Episodes season, than 2 1/4 seasons), it had a ripple effect on how comedy was done on TV, to the point where I’m not entirely sure that it has been matched to this day. Chappelle took what Keenan Ivory Wayans did with In Living Color, & not only updated it, but enhanced the content & pushed the boundaries further (a perk of working on Comedy Central instead of a major network like Fox). It was a classic, classic show that’s remembered fondly because it only lasted two seasons. It never got a chance to lose top writers, change actors, or get stale after a few years like Martin did after Season 3 or what The Real Husbands of Hollywood is going through since Season 3 started. Of course, it was a self-imposed walk off from Dave himself, that unfortunately ended its reign, however, because of the short time it was on the air, the legendary shine never had a chance to have its sheen rubbed off.  

Now, we all remember the classic skits that made the show what it was. From Black-White Supremecist Clayton Bigsby, to the R. Kelly “Piss On You” videos, to Tyrone Biggum and the Mad Real World, to Making the Band, to Rick James & Wayne Brady, the show was immortalized by those legendary skits. But much like a championship team, stars alone does not a team make. You have to have the right set of role players that know their roles & play calling that make everything work. It’s about attention to detail, paying attention to every drill, every word, all the little things that makes anything great. In the case of the Chappelle show, as special as the aforementioned skits were, it was some of the other underrated skits that enhanced the level of the show. Today, on #FlashbackFriday Videos, we’ll show you a scattered collage of the most underrated skits that helped make the Chappelle’s Show one of the most influential shows in TV History.

**** WARNING: Some of these videos contain swearing & course language. ****

“Knee High Park”

This sketch is so, so genius & so, so wrong at the same time. Especially after the 1st puppet takes a hit of heroin & ends his song with foam coming out of his mouth. I think part of why I love this skit so much is that it’s an extension of his bit that he did on his “Killing Them Softly” concert a few years before, when he breaks down the stereotypes of Sesame Street. Back when I first saw this sketch, I knew where the foundation of the idea originated from. If you watch that concert clip hyperlinked two sentences ago, you’ll understand this sketch entirely. Also features Snoop’s voice as “Dangle” and Q-Tip singing a song about STD’s. Favorite lines from that skit are: 

“You don’t understand / Is I make love to my hand / so I don’t need you honey / I beat my **** like it owes me money….” – The “F**k It Song 

“Well hello Dave Chappelle! Haven’t seen you in a while. What’s it been? Two months??” – The end of the Gonorrhea song after Gonorrhea turns around and sees Dave for the first time. 

“When Keeping It Real Goes Wrong”

It’s one thing for the content of this sketch to be a funny as it is, but it goes to another level when you use the narrative voice from the infamous NFL Films to actually narrate it. The ones with David getting his ass kicked in by his girlfriend and some random dude at the club, and the girl who goes nuts when someone calls her by mistake and hangs up are great…… but it’s something about this episode of Dave reacting poorly to his boss giving him a racially awkward high five. I think most black men have been in the position of being turned off when this happens to them at work, when their boss or co-worker wants to be “cool” with you by giving you an awkward handshake or using outdated or similarly awkward slang to try to relate with you (ie. “Hey Cal! How’s it hanging bro? Yeah, I can dig it!). Usually you just say “hello” back and you keep things moving. So it’s interesting to see the flip side of what someone would do in that kind of situation. Of course though, Dave takes it way too far. Bonus points for barking like DMX & throwing up the Ws for Wu-Tang. 

“The Niggar Family”

Part of what made Chappelle’s Show, was the lack of fear to push the racial boundaries & tackle those issues, discussions, and debates through Dave’s comedy. As we found out later, it was also something that he struggled with while doing the show at times. However, above all else, Chappelle, Neal Brennan & his writers would make up these crazy situations, scenarios, mixed in with racial aspects that were as well planned out as they were funny. I think having a sketch based on a white family that happens to be called Niggar is probably a highly qualified example. 

“2Pac is Still Alive?”

After Tupac died in Sept 1996 (damn, it’s almost 20 years already?!), he essentially became the Hip Hop version of Elvis. With all the albums & music that was released after he died, there were many people who thought his death was a hoax & that he was recording tracks either in a hood in Oakland or somewhere in Cuba close to the beach. Some of his lyrics were so ahead of his time that they sounded like he did them the night before (as some people felt anyway). So naturally, Dave touches on this early 2000’s pop culture topic. Based in the club, Dave and the rest of club goers are dancing when Questlove the DJ premieres a new Tupac song. Everyone is hype about that song at first, but then get confused as Tupac touches on topics so relevant, that he’s describing people in the club (which includes scolding Dave for dancing on a woman whose not his wife). 

It’s an underrated/lost sketch because it released after Chappelle left the show & Comedy Central still went on to air 3 episodes worth of new Chappelle material that people barely remember. Comedy Central then went on to package & sell those lost episodes on DVD making sure they squeezed every single last drop of potential Chappelle income they could collect on. Smh…… 

“Player Hater’s Ball”

Dave, Charlie Murphy, Donnell Rawlings, & others dressed up as pimps hating on anything & anyone at a Hater convention? I’m not sure what else needs to be said, but I know you started smiling already. Admittedly, I’m not entirely sure that this one falls under the underrated umbrella. In fact, I think it walks the line between being legendary & being underrated. I only rank this as underrated because it doesn’t get discussed as much as the other legendary ones, but it should absolutely fall alongside with them. It’s the equivalent to Cris Carter getting rejected for years and years from the Football Hall of Fame until finally getting selected. This sketch is knocking at the Legendary Level doors with its measurements in its hand to give to the committee, so that it can be fitted for their Hall of Fame yellow jacket. 

Underrated line of the sketch: 

“Why don’t you click your heels together three times……and go back to Africa?” – Silky Johnson 

“Dancing For Different Cultures”

Another thought-provoking sketch that breaks down each race and culture by which musical instruments make each of them lose control. Conducting the sketch like a social studies project, Dave & Jon Mayer go to different settings to see how influential his guitar riffs are over white people. Once he gets shot down by the Black & Hispanic customers at the local barbershop, he brings out Questlove on the drums and Sanchez on the keyboards to see if they fall under the influence of their instruments as well. Bonus points for Chappelle Harlem-Shaking while a cypher breaks out once Questlove starts drumming, as well as the repeated G-Unit shoutouts.  

Common “The Food” ft. Kanye West

“I walked in the crib / Got two kids / & my baby mamma late / uh oh! uh oh! uh oh!….” 

Based on the friendships Chappelle had with some of the hottest musicians at the time when he was putting his show together, ending the show with live musical performances was probably the most predictable thing to happen from that. With that said, he brought that format to a very unique level. Instead of having them perform in front of the live studio audience or at Club Natalie’s a la New York Undercover, he brought it to venues where the artists felt comfortable. They would shoot you singing or rapping on the street, at the library, in front of a urinal fresh off of using one, didn’t matter. We got a chance to see Mos Def freestyle in the shotgun seat with Dave driving, Wyclef singing “If I Was President” with his guitar at the studio, Kanye, Freeway, and Mos Def rapping “Two Words” on a triple decker bus, and countless other performances. My personal favorite however is Common performing “The Food” with Kanye simply because of where Common’s career was at the time. 

After crawling out of the Knitted Clothing & Crochet Bubble (in other words, dating Erykah Badu and fully embracing her essence), & putting out Electric Circus, his career was at a crossroads. Common needed a win. Badly. His credibility as a rapper was taking some shots, & people thought he was done because of the image changes he made. I never thought to question Common’s abilities as a rapper. In fact, you go back & listen to it, Lyrically, he didn’t really go anywhere. But the knitted hats/shrit combos though….yikes. Then fellow Chicagoan Kanye West fresh off his College Dropout album was starting up his G.O.O.D. record label & needed artists to sign. He convinced Common to hop aboard & gave him a lifeline by producing the majority of the classic comeback album “Be” (save for a couple of J. Dilla beats), which holds up beautifully even 10 years later. While the album was being made, there was a heavy buzz about the collaboration but no one really heard anything from it as yet, so for a lot a people, that performance on Chappelle’s Show was really the first time we got to see “Comeback Common.” It was an unexpected premiere-of-sorts, much like when a rapper nowadays unexpectedly debuts a new song at King of Diamonds, with a stripper twerking on your left shoulder, while you decide whether or not to have the mild or spicy chicken wings. Okay, maybe not so much.  

The Food performance remains so memorable because at the time, a) it was the hottest shit we heard from Common since “Like Water For Chocolate”; b) “College Dropout” era Kanye was joined at the hip regardless of the success of his own album; & c) they were rapping from a makeshift kitchen, with Kanye popping up from behind the counter to spit the chorus. It was the hottest musical performances from that show, & once they ended the song with their fists up, you knew Common was back. Not saying he wouldn’t have gotten there without performing on Chappelle’s Show of course, but it made for a very cool, authentic moment.   

“Law & Order”

Dave presents a bizarro-world scenario where the drug dealers get the fair treatment in court while the white corporate business gets the book thrown at him. It’s another thought-provoking social experiment flip on the idea of how blacks and whites are perceived in the court of law. It’s a hilarious perspective watching “Tron the Drug Dealer” get away with so many infractions of reckless behavior here. 

Underrated moments in order: 

3) When Tron explains why he was more than 6 hours late to his meeting with his lawyers, 

2) When Bill Burr’s character explains what went down during the arrest on the witness stand, 

1) When the judge reads the plaintiff the riot act which ends with him calling him a “Filthy, big lipped beast”, and telling him to go lift weights & convert to Islam.

Cal Cee // South Shore Ave

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