DAR TV: Top 5 Sketches From Each Season Of Chappelle's Show

By @TrueGodImmortal

So, the Chappelle's Show is legendary television. Over the years, Dave Chappelle has become a legend in his own right for several reasons, and today, we wanted to look back on where his legendary run truly hit the pinnacle. Sure, Chappelle had appeared in multiple movies and had a classic standup under his belt, but it wasn't until he officially hit the big time utilizing his sketch comedy show that he really crossed over in a major way. Today, we look at the three seasons and list our choices for the five best sketches of each season. Which sketches do we select? Let's take a look.

Season 1
The first season of Chappelle's Show is amazing. We rated the season 8/10 on an older article, but today, I wanted to list my choice for the 5 top sketches of the season. Which sketches make the list? It is really tough to list them because there are so many legendary ones, so a few of them like the R. Kelly and Gang Wars sketches, among others, will miss my list but they are classics for sure. So which sketches did we choose? Let's take a brief look.

*The Mad Real World
-If I were to rank these from the season, I have no idea where this would end up honestly. I love this sketch so much and it is one of my personal favorites. Everything from Chappelle as Tron in this to Charlie Murphy and his hilarious moments to the infamous "I had sex with Katie" debacle made this an all time classic. If you don't appreciate the Mad Real World sketch, then shame on you.

*Clayton Bigsby
-So, I begrudingly put this on the list for a few reasons. It was the first sketch that caught the mainstream eye and attention, as Dave played a black white supremacist who happened to be blind and was unaware he was black. The genius behind the sketch is more important than the sketch itself, and the legacy of said sketch has it high up on any Chappelle sketch list. Clayton Bigsby is a classic sketch.

*Player Hater's Ball
-This is a legendary sketch for so many reasons. It is my favorite sketch from the first season and it might be my favorite of all time. Chappelle, Patrice O'Neal, Donnell Rawlings, and Ice T carry this sketch, with nothing but quotes and comedy throughout the sketch. I quote this sketch personally often and think it might be the greatest work that Chappelle put together for the show. I'm sure many feel different, but if I were to rank the sketches in the order of quality, this would be no. 1. There is no moment greater than the Player Hater's Ball on the first season of Chappelle's Show, in my humble opinion of course.

*Trading Spouses
-Leonard Washington. Nuff said. Really, that's all I need to say. Leonard Washington is a legend. His legend starts from this sketch. Chappelle plays both Leonard and a white man who swap wives for a while and the hilarity that ensues is laugh out loud funny. For me, Leonard Washington is quote after quote hilarious, and watching the way he navigates this character is classic Chappelle. Trading Spouses is one of the funnisst sketches in the show's history so naturally it has to make the top 5 of Season 1.

*Tyrone Biggums Classroom Visit
-So, I thought about it. I really did. I almost put another sketch here. However, I found it really tough to place any other skits above this one and I still can't imagine anyone denying the legend that is Tyrone Biggums. The ridiculousness of this entire sketch, made funnier by the kids in the classroom earns this one a spot in the top 5 of season 1. If I were ranking these, I would probably have this one at 3 or 4, maybe even 5. Regardless, Tyrone Biggums, Mad Real World, Player Hater's Ball, Trading Spouses, and Clayton Bigsby are the top 5 sketches of Season 1.

Season 2
This season is the pinnacle of Chappelle's Show. Every episode felt classic and the show became a nationwide sensation. There are so many sketches to choose from that personally, I know many of you will have a different top 5. There will be classic sketches missing from my top 5 choices like the Samuel Jackson beer sketch, The Niggar Family sketch (I know, I know), The Racial Draft (I know man.... I know), the Lil' Jon sketches, and more. What sketches do we choose? Let's take a look.

*Black Bush
-So, I know many people might have picked a different choice, but I think Black Bush is the most underrated classic sketch in the show's history. Chappelle is hilarious as the Black Bush, with Jamie Foxx playing Black Tony Blair, and even Mos Def getting in on the fun. All in all, this was a great sketch that should get more love, as it might be a top 3 sketch for the season.

*Charlie Murphy's True Hollywood Stories: Rick James
-Of course, the GOAT sketch in comedy might be this one. It was the sketch that broke everything through for the show, as the world took more and more notice to Chappelle and his brand of comedy due to this sketch. Rick James, Charlie Murphy, and Chappelle all saw a surge (or resurgence if you will for Rick) in popularity and this is probably still the most quoted thing in Chappelle's Show history and perhaps Chappelle's entire career. The legend of Rick James with his Unity ring, punching Charlie, and everything else in between is epic and iconic. RIP to Rick James and Charlie Murphy.

*Charlie Murphy's True Hollywood Stories: Prince
-Perhaps the spacing of these two Hollywood stories were too close together, but I sometimes wish we got more than those two sketches. There has to be more stories that we never witnessed and to be honest, I just wish we had Charlie here to tell them. I mean, who could deny the legend of Prince playing basketball, winning the game, then making pancakes. Everything about this sketch is comedy and it is easily top 5 on the season, maybe even top 3. It's that good! RIP to Prince and Charlie once again.

*Wayne Brady's Show
-So, I was never a Wayne Brady fan. I still am not. However, when I watched this skit, I gained a bit more respect for him. He went from the extremely corny token black guy character to a ridiculous funny comedian who could do a multitude of things with one sketch. He played the aggressive role on this sketch and it worked to my surprise. Wayne would scare the hell out of Chappelle, dominate his screen time, and dispel the notion that he made Bryant Gumbel look like Malcolm X. All in one sketch. This is beyond a classic.

*Making The Band
-So, of course. Chappelle as Dylan and Puffy. I mean, is there anything funnier than this? You add in the Wyclef appearance along with the actual group Da Band appearing in the sketch and the hilarity is magnified that much more. Sure, there are other sketches that could have made the list over the 5 I selected, but that is the beauty of the second season of Chappelle. Every single sketch could have made this list because there were no misses. These are just my 5 personal choices (I'm resisting the urge to make a Dylan and spit hot fire reference).

Season 3/Lost Episodes
These lost episodes were considered the third and final season so it is hard to pick 5 sketches out, but if I had to make a list, I have my 5 picked out. Here are the 5 sketches from the lost episodes that resonated better than the rest.

*Dave Has 55 Million
-So, this sketch was simple but pretty funny. Dave would earn a huge contract from Comedy Central for Season 3 and it would make the news and be a huge deal for the amount he would receive. Unfortunately, that would bring about a lot of watching eyes and people bothering him. This sketch is actually one of the rare hilarious ones featured on this shortened uneven season.

*2Pac Is Still Alive 
-I loved this sketch because of how authentic and honest it was. Many of us have heard things in Pac songs that make you think he is still alive, and this sketch sums up our feelings, from Pac talking about the women in the club currently to even mentioning Grand Theft Auto: San Andreas and calling out Chappelle while he's dancing at the club, this definitely sounds eerily like a real Pac record just slightly exaggerated from the beat to the flow to the lyrics. This sketch was a winner and a classic IMO.

*Dave On MTV Cribs
-So, this was a part of the Show Business sketch, but it was important to separate it as its own entity honestly because it is a classic and one of Dave's shining moments on the show. Dave takes us through his "home" showcasing the luxury he lives in and even has a sweatshop in his home, which is another laugh out loud moment. He has dinosaur eggs, sprinkles diamonds on his food, and does everything baller. This is a classic sketch.

*Dave Meets Show Business 
-While this sketch was sort of combined with the MTV Cribs one, I separated them on purpose. The Susan Sarandon bit was slightly funny with the Lil Jon mix, and the cereal bit was funny too, but it was between this one and the Howard Dean sketch and the Howard Dean sketch lacked the layers of this one. Not a classic sketch by any stretch, but it was solid for this season at least.

*Dave Gets Revenge
-So, I always go back to this sketch for some laughs because it is the essential "I'm petty" sketch in reality. Dave strikes it rich, moves on with his life, then decides to repay some of the people who wronged him in life. In reality, this would be some loser shit to even think of, but in a sketch form, it is beyond hilarious. The best part of the sketch is Dave getting revenge on an ex that left him, and he has quotes throughout that part of the sketch. Is this a classic sketch? Not necessarily, but it is a top 3 choice for this short season.



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