DAR TV: Rating The Seasons Of Chappelle's Show

By @TrueGodImmortal

Dave Chappelle is one of the greatest comedians of our time. That much is a fact. Over the years, we've watched him showcase why he is one of the most gifted and genius comedians ever, but the biggest piece of his legacy remains his sketch comedy show. Comedy Central would give Dave a platform and he would take their network higher than expected with some of his iconic sketches and characters. With the 13th anniversary of the second season's DVD release coming up, I wanted to take a moment to revisit the two full seasons and one small season of lost episodes for Chappelle's Show. This isn't a ranking, but rather a review of each season, a look at the best overall episode and a rating of the entire season on a scale of 1 to 10. Which season is the best? What are the best overall episodes? Let's take a look.

Season 1
The first Chappelle's Show season was interesting for sure. I always believed that this season was in some ways better than the acclaimed and loved Season 2, but the more I revisit the show, perhaps I was wrong. The season begins with one of the most impressive sketches in the show's history, as the Frontline sketch showcases the black white supremacist Clayton Bigsby, but that's one sketch on an entire episode. For me, the rest of the sketches on episode 1 are decent, with Popcopy being a standout, but nothing special. Episode 1 was good, but outside of the Clayton Bigsby sketch, nothing really hit hard. Episode 2 was actually pretty subpar, as the episode starts off with a random white woman singing Dave's thoughts. Honestly, that could have been cut out of the show because it added nothing to it. The Real Sex HBO interview was pretty funny, though it was short, but it was solid nonetheless. The Wrap It Up sketch is infamous to many, but it doesn't hold up that well. Of course, episode 2 is well known and loved for the amazing introduction of Tyrone Biggums during his classroom visit to a group of small students. Episode 2 was subpar overall, but gave us a classic character and sketch, so it is very important to the show's lineage.

Episode 3 was another hit or miss episode, but you could see the show starting to get into form. While the QVC and Zapped sketches were mostly expendable, the Roots parody sketch and the slightly corny but funny It's A Wonderful Chest sketch are the highlights. Episode 3 doesn't improve much on what episodes 1 and 2 lack, but it does set the foundation for what would become the best episode thus far with Episode 4. This episode would have one minor dud, but everything else here was solid, especially two of the most hilarious skits with the Reparations 2003 being one of my favorites and the infamous New York Boobs sketch. Episode 4 benefits from having two back to back classic sketches, and the Reparations sketch still provides huge laughs even today. Episode 5 was another important episode in the continuing growth of the show, with the sketch featuring rappers endorsing their own products, as well as the underrated Greatest Moments in Hookup History. While there weren't any classic sketches on this particular episode, it had enough of a consistent flow that there were never any moments on this episode that felt like it dragged along.

The show would reach a new high with episode 6, as this would be one of the best episodes overall on the entire show. Featuring the classic sketch for Mad Real World, the show was mostly dominated by this skit. Along with the hilarious skit about Chappelle having his own biopic and the surprisingly funny segment Ask A Gay Guy, Episode 6 takes the reigns as the best episode of season one so far. The only sketch that didn't inspire a ton of laughs would be the Third World Girls Gone Wild sketch, but that was still decent enough to not drag on too long. Episode 7 is a mixed bag, with some quality sketches and a few misses, with the Real Movies sketches being the misses on this episode. Everything else here is solid and a joy to watch, including the Wu-Tang Financial sketch, which is one of my personal favorites. The Jedi Sex Scandal is actually underrated to me, as I find that Chappelle as Samuel L. Jackson is one of his funniest impressions. Episode 7 is a solid watch, and I think the same could be said for Episode 8 as well. While I was not the biggest fan of the Real Movies skits (the worst of the reoccurring sketches on the show), I did enjoy the return of Tyrone Biggums, even though this sketch with his return doesn't rival his initial one. I even think the Racist Hollywood Animals sketch was pretty funny, and I'm surprised James The Nigga Hating Dolphin isn't mentioned more when this show gets discussed. Episodes 6-8 present the most consistent flow of episodes thus far in the show, could Chappelle keep it up for the rest of the season?

The answer was yes. Episode 9 takes the title from Episode 6 as the best of the show so far, with one of the greatest sketches of all time featured on this one. While I enjoyed the GTA related sketch and even laughed at Blackzilla, the highlight here is the iconic Playa Hater's Ball, which might be my all time favorite sketch. Ice T is hilarious here, and Chappelle is at his best as Silky Johnson, the most diabolical hater of them all. Every character is classic, every piece of dialogue is special and every moment is hilarious here. Episode 9 is an amazing watch, and it leads right into my favorite episode of the season, Episode 10. With a hilarious turn from Mos Def here, along with some excellent comedic timing from Chappelle, the History's Greatest Wars sketch is a true gem. It is one of my favorites from this season and probably the most underrated sketch from Season 1. Ask A Black Dude and the Real Movies sketches are smaller and not as prominent, but still enjoyable, but this episode is made infamous by the R. Kelly parody "Piss On You". I remember my first time watching this and I think I might have shed a million tears of laughter just from the opening lines.

Everything about Episode 10 is perfect and after Episode 3, it seemed as if Chappelle had found a great rhythm for the show. That would continue into the 11th Episode of the show, which wasn't as good as the 10th, but still kept the consistent laughter coming. The Fisticuffs sketch was great, the Make A Wish sketch was hilarious, and even though I could have done without the Crazy Camera sketch, it had some good moments and great laughs. Episode 11 wasn't too special, but it was a good watch. Episode 12 however, might be the most underrated episode of the entire show. Minus the silly O'Dweeds sketch and the sophomoric Diarrhea skit, the show manages to bring two amazing classic sketches that sometimes go ignored by the masses. The And-1 sketch is a true gem, and of course, Trading Spouses is a classic sketch. Leonard Washington is a legend and this was the sketch that solidified his legend. The whole premise was hilarious of course, but Leonard Washington just stole the show here. There are so many quotes on this sketch that I could write a separate article on this single skit. Episode 12 closes out the first season of Chappelle's Show in a very strong way. While there are some critical misses early on in the season, for the most part, the first season shines with some of the greatest sketches in comedy history. While Season 1 didn't take off in the way that Season 2 did, it is still a great season overall and enjoyable from start to finish with only a few minor mishaps.

*Best Episode
Episode 10 is by far the best episode for this season. Ask A Black Dude was solid on this episode, and even the Real Movies sketch for Deep Impact was pretty funny. Of course, two classic sketches dominate this show, with the History's Greatest Wars sketch being an underrated favorite, and of course, the R. Kelly parody remains one of the all time greatest sketches in sketch comedy history. I considered Episode 9 and gave some thought to Episode 12, but Episode 10 takes the cake for sure.

Rating: 8/10

Season 2
The apex of the show by far. It felt like almost every sketch was a winner on this season and everything felt magnified in terms of quality. The season kicks off with a classic first episode, starting with Samuel L. Jackson beer and finishing off with the iconic Racial Draft. The Better In Slow Motion sketch is also a part of the first episode and it is pretty hilarious as well. Right out the gate, Chappelle delivered a classic episode. As if Episode 1 wasn't good enough, Episode 2 comes right back with more fire, starting with the supremely underrated WacArnold's sketch, which is a hilarious take on commercials of the past. While Negrodamus and Black Gallagher are pretty funny, nothing compares to the genius of the Niggar Family sketch. Chappelle executed this with poise and as a result, the sketch turned into an instant classic. It is one of my favorites and one of the most quoted sketches from this season. Episode 1 and 2 both come out the gate with greatness, placing Chappelle's show Season 2 on a better trajectory already than Season 1. Could they sustain the quality for Episode 3? Yes. Episode 3 is another quality episode, this time with two classic sketches and one sketch that was so ridiculous, it would work. The Ribs sleep aid sketch was stupid, but ended up being silly fun, however, White People Dancing and the 3 Daves sketches are top notch quality. Both of those sketches provide endless laughs and are some of my favorite for this season. Chappelle gets off to a running start with the first three episodes of the show.

Episode 4 takes the season to an even higher level. With only two true sketches, the show gets off to a funny and ironic start with The Love Contract before hitting the pinnacle with the classic and undeniable Rick James sketch through the iconic Charlie Murphy True's Hollywood Stories. This was a great episode and we all know the legacy of Chappelle as Rick James. Literally 4 episodes in and Chappelle didn't miss once on a sketch. That is amazing on so many levels. Episode 5 continues the vibe set by the first 4, with Negrodamus and Tyrone Biggums making appearances in hilarious scenarios, and the return of the hilarious Tron for a classic Law and Order sketch before arriving at what I feel might be the best sketch in Chappelle's Show history. Another Charlie Murphy's True Hollywood Stories arrives in the form of a sketch on Prince and it is beyond classic. Prince plays basketball, serves pancakes and provides more comedy than expected. Once again, this is yet another excellent episode with an all time great sketch, and Chappelle goes 5 for 5 with his episodes. Episode 6 isn't flawless, but it does introduce the classic moment with Chappelle playing Lil' Jon, which leads to a few comedic scenarios. The only sketch that disappoints a little bit is If The Internet was a real place, but the episode ends strong with a pretty funny sketch titled When Keeping It Real Goes Wrong. Episode 6 is the first episode to have a sketch that slightly misses, but overall, the episode is pretty damn good. Chappelle goes 6 for 6 to kick off Season 2, does he ever cool off or have a decline this season?

The answer is no. Episode 7 is solid, with no weak sketches, and one of my favorites here, with the World Series of Dice bringing in Eddie Griffin for a hilarious turn and the return of the legendary Leonard Washington, as well as the genesis of Ashy Larry. Another edition of When Keeping It Real Goes Wrong makes this a well rounded episode, with no misses to speak of. Episode 8 continues the vibe, but this one is a little different. It isn't a classic episode, but it is entertaining with two segments dominating the episode. The I Know Black People sketch is pretty funny, and of course, any edition of When Keeping It Real Goes Wrong makes an episode hilarious. In what might be an unprecedented achievement, Dave comes out swinging and connecting on all 8 episodes to start the season off. It is impossible to pinpoint an apex for the season because it keeps up the consistency throughout, and Episode 9 is just as good. Episode 9 starts off with an excellent sales pitch sketch that features a hilarious appearance from Arsenio Hall and it also has the iconic Oprah sketch. The episode finished off with the solid Jury Duty sketch, where Chappelle has quotes for days. Another solid episode, and there are no misses or weak sketches here. Chappelle really went 9 for 9 in his second season and guess what? The 10th episode held up that standard as well. The 10th episode features one of the greatest sketches ever in comedy, as Chappelle plays the role of Puff Daddy in a Making The Band sketch. The Making The Band sketch is definitely one of the best from this season, and it starts off the episode and dominates most of it. Another great sketch on this episode is of course the Kneehigh Park skit, which is essentially just a parody of Sesame Street. Snoop Dogg makes an appearance and so does Q-Tip, and even Tyrone Biggums shows up at one point. 10 episodes in and Chappelle hasn't had a regular or ordinary episode thus far. How do you celebrate such a success?

You celebrate by showing an episode that is essentially your worst sketches that made the cutting room floor. Episode 11 is a throwaway, but it doesn't suck. It isn't a bad episode at all and has some solid sketches surprisingly. I laughed at the Gay World sketch because it is pretty funny yet also slightly where the world seems to be heading in certain sectors. Friday Night Sissy Fights is one of the most hilarious terms ever and the guy with the lawnmower will always be funny. The Playa Haters return with a time machine, and as bad as the sketch should be, it has some funny moments. Episode 11 was meant to be a bad episode and it wasn't. That's how good Chappelle was. Episode 12 is the most interesting twist. A majority of this episode features Wayne Brady. Wayne Brady takes over the show and we get nothing but hilarious moments in every scene he has. An underrated sketch comes from this episode as Tyrone Biggums returns to take part in Fear Factor. However, this episode is all about Wayne Brady. If you watched the show, you know all too well about this episode so all I need to say is that Wayne Brady left the world with many quotes. Episode 13 was the final episode of the season and it delivered. Aside from a solid Lil' Jon sketch and a pretty funny sketch about the first black man to use a white toilet, this episode features another classic with Black Bush. Black Bush was just ridiculously funny from start to finish and is a top 5 sketch from this season without question. As Season 2 came to an end, Chappelle had done the unthinkable. He made a flawless season of television. In sketch comedy. That has never been done before, nor will it be done again. For that alone, Season 2 of Chappelle's Show is one of the greatest TV seasons ever.

*Best Episode
I really couldn't decide. I lean towards Episode 5 just due to Negrodamus, Tron on Law and Order, and the Prince sketch, but The Love Contract and Rick James sketches are tough to beat. If I had to make one choice, I lean towards Episode 5, but Episode 4 is right there. Those two are the best, but the entire season is classic. That's not a bad predicament for any show to be in.

Rating: 10/10

The Lost Episodes
The glorified third season of the Chappelle's Show needs no discussion really, but I'll include it here just for the necessary purposes of talking every episode on the show. Hosted by Donnell Rawlings and Charlie Murphy, this brief season of episodes would only highlight the leftover sketches from the show's unfinished third season, with Dave not really giving Comedy Central their blessing. Still, despite this, there were some gems and decent sketches. The first lost episode showcases Dave getting 55 million and the fallout from it, a segment on the news if it was only shown through hip hop lyrics, Dave and his need for revenge now that he has newfound fame and money, and the highlight of the show, a new Tupac song that plays in the club. The Tupac sketch is hilarious and one could imagine that the lead in to it from Dave during an actual third season would have made this sketch just as popular as a Prince or Rick James sketch. Still, the first episode was solid and might be my favorite overall in this season of lost episodes.

Episode 2 however is actually pretty bad. The Black Howard Dean sketch is mildly funny, but the Gary Coleman sketch is just brutal. It feels generic and just doesn't seem to really get going like it should. The Pixies sketch is funny, but the controversy around it makes it not nearly as funny as it could have been. Something was missing in this episode and it really just didn't work. Perhaps this would have been better if Comedy Central only aired two episodes instead of three. The third episode and the final one of this lost season is decent, and that's only because of one sketch. The other sketches really don't matter here, as only Dave Meets Show Business provides immense laughs. It almost feels like a sketch that shows you exactly how phony Hollywood is and how the system works, which wouldn't be shocking. Dave is hilarious as Lil' Jon, and even funnier when he does MTV Cribs. The MTV Cribs sketch is one of the funniest things I've ever seen on Chappelle's Show and it genuinely leaves you wishing Chappelle came back and finished what he started. All in all, the lost episodes season is subpar, with about 60% of the sketches being enjoyable, but that other 40% is nearly unbearable, a sign perhaps of these sketches not being presented how Chappelle really wanted them to be.

*Best Episode
Episode 1. Of the episodes here, the most consistent is the first one. The Tupac sketch, the 55 million dollar sketch, and Dave Gets Revenge are all top notch sketches with hilarity from start to finish. Episode 3 is the only other choice and it falls flat in some areas, like most of this season did. There is slightly more good than bad, but this "lost" season just doesn't feel right in general. If only Chappelle was there to deliver this how he envisioned from the start.

Rating: 6/10

Chappelle's Show is a legendary show that gave us so many classic moments, and this rating of the seasons showcases that. Season 1 was really good, but the early struggles showed that Chappelle was finding his footing in the TV world. Once he got comfortable with his show, the quality continued to go higher and higher. Season 2 is the rare perfect TV season and it features so many iconic sketches. While the last short season isn't that good, it does at least give us a few great sketches. Simply put, Chappelle's Show is one of the greatest shows in TV history and a lot of that is due to having one of the greatest seasons ever in television and enough consistency throughout. Long live Chappelle.



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