Chappelle’s Show Power Rankings: Season 2

John Mosley ranks each and every episode of Chappelle's Show season two.

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Back with my rankings for season two’s episodes. If you missed season one be sure to head over here (Stoney does his magic) to see how the inaugural season of Chappelle’s Show shaped up. 

Chappelle’s Show Power Rankings: Season 2

1. Episode 4 – The Charlie Murphy True Hollywood Story of Rick James. The absolute number one episode in Chappelle’s Show history for me. There’s no way to tell how many times “I’m Rick James, bitch” was said after. The number is just so high. But not on cocaine. That’s a hell of a drug. 

2. Episode 12 – The Wayne Brady show took over for a week until Dave showed just how crazy Wayne was. Second only to the Rick James line we have to take a moment to appreciate “is Wayne Brady gonna have to choke a bitch?” as a line of pure comedy. I had to explain Wayne Brady to Haley for her to remember him so this episode may get lost on audiences that missed it. This week also brought Tyrone Biggums on Fear Factor which is pure gold. Fun fact: this skit is why I always refer to Joe Rogan by his full name at all times. 

3. Episode 5 – The meat, potatoes and dessert of this episode is Charlie Murphy back and telling a true hollywood story about Prince. Like the previous two episodes, I can vividly remember where I was when I saw Prince playing basketball. I’m laughing just thinking about it again. The skit is so good, we forget that this episode has other solid bits like the excellent Law and Order spoof as well as Tyrone Biggums in a “Red Balls” commercial. Such a stacked episodes. 

4. Episode 1 – So how do you follow up the classic season one opener? Well with the ‘Racial Draft,’ that’s how! Another all timer from Dave that would not find its way on television in 2020. The season opens with ‘Sam Jackson Beer’ and Dave showing us how cool every day life would be if it were in slow motion. Solid stuff all around. 

5. Episode 10 – ‘Making the Band’ and ‘Kneehigh Park’ are ribs-hurting-from-laughter good. Dave as Diddy wanting “the finest of breast milk” may be an underrated moment in comedy history. We also get Dave’s Sesame Street spoof ‘Kneehigh Park,’ which doesn’t get enough love. Charlie Murphy as the grouch will forever make me giggle. Snoop Dogg also performs with Tyrone Biggums dancing. What more do you need?

6. Episode 7 – Highlighted by ‘The World Series of Dice,’ this episode packs more smaller skits rather than a big one or two. ‘WSOD’ stands out with Dave back as ‘Leonard Washington’ and Bill Burr on commentary. It’s supplemented with a ‘Moment in the life of Lil Jon’ and another classic ‘When Keeping it Real Goes Wrong,’ which are both very good. We also get Paul Mooney back with ‘Mooney on Movies,’ which is obviously fucking hilarious. A performance from Kanye and Common caps off this gem. 

7. Episode 8 – The first and last edition of “I Know Black People” was played with hilarious results. Dave just asking questions and having fun with the ‘contestants’ is an absolute blast. Another “When Keeping It Real Goes Wrong” and a performance by Erykah Badu wrap up the show. No real big “moments” from this week, but still a lot of laughs here. 

8. Episode 3 – Most people will probably remember this episode for Dave/John Mayer/Questlove going around and playing music for various ethnicities. This is gold, but my favorite sketch from the episode is ‘The Three Daves.’ In it, Dave shows how he would handle issues at the age of 18, 24, and 30. There is so much to love in this sketch including Dave yelling “FUCK NICK CANNON,” which will always make me laugh. Super underrated stuff here. 

9. Episode 9 – The ‘Jury Selection’ skit is one of my least talked about favorites from the season. Dave goes through the process of being a juror for various celebrities including OJ, R. Kelly, and Robert Blake. If none of this is ringing a bell, go watch this episode ring now. Along with that great piece of business, we get a “Oprah as Dave’s Baby Mama,” which is as crazy as it sounds. A very slept on episode right here. 

10. Episode 2 – If Comedy Central thought “hey episode one this season wasn’t thaaaaat crazy. maybe Dave is calming down,” episode two ends that thought real quick. Paul Mooney debuts ‘Negrodamus’ while Dave portrays ‘Black Gallagher’ in one of the wildest episodes ever. All of this is light compared to a 60s sitcom spoof about a white family with a racial slur as their last name which ends the episode. 

11. Episode 13 – A historic look at “The First Black Man to use a White Toilet” opens before getting into another “Moment in the life of Lil Jon.” Both are solid, but Dave as George Bush aka ‘Black Bush’ is one of the best bits of the season. I can’t be around yellow cake without quoting this episode. Think about that. 

12. Episode 6 – ‘The Internet as a Real Place’ hits harder now more than it did back then. The grossness can’t be described but Dave does a good job trying. Two ‘Moments in the Life of Lil Jon’ and a new edition of “When Keeping It Real Goes Wrong” round out the week, which also includes one of my favorite performances of the year with Anthony Hamilton doing the damn thing. 

13. Episode 11 – Basically a clip show with sketches that didn’t make any of the shows. It’s ok, but outside of a Nelson Mandela scaring kids straight spoof and the time traveling player haters, there’s nothing here really worth seeking out. 

John Mosley is the independent wrestling and TV aficionado of the SoBros Network. He graduated from ETSU with a degree in Radio, TV and Film along with a minor in Film Studies. Since graduating he’s done pretty much nothing but watch, film, edit or commentate for local wrestling promotions and is the current color commentator for Resolute Wrestling. #Preds #Titans #DefendOrVacateConor. Follow on Twitter: @SoBroMose

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