Every so often, Pepster and I get together to do big, irrelevant, time-consuming things that only make sense to a few people. A couple of months ago, a significant birthday and trip to Chicago provided the backdrop of one more of those important moments.
It was 10 years ago that we got together with the idea of determining which was the best of the ESPN 30 for 30 series. After some debate, we decided that we would rank the first 48 episodes of the series (including the 14 ESPN Films Presents) from best to "I didn't even care that happened." This was done as a snake draft, so the coin flip to determine who went first was as dramatic as any argument we had that day. And there were a lot of arguments!
Pepster won that draft and I now have to accept that The Two Escobars is the best of the early 30 for 30 episodes. If you were wondering what would have been first had the flip gone the other way, it was the obvious choice of Benji.
- The Two Escobars
- Benji
- You Don't Know Bo
- June 17th, 1994
- The U
- Once Brothers
- The Fab Five
- Ungarded
- No Crossover: The Trial of Allen Iverson
- Pony Excess
So, what thing would we do in 2023 to anger people close to us looking to spend meaningful time on vacation? There was only one answer. The best episode of Chappelle's Show!
The rules were simple. We would again flip a coin to determine the first pick with a snake draft following for the 28 available episodes. Yes, we included the questionable third season. The goal was to pick the best episode, not skit. So, we were evaluating the strength of the best skit in the episode, the quality of the remaining skits and the musical performance where applicable. Sinickal won the toss and the draft went as follows:
1. Season 2, Episode 4 - True Hollywood Stories: Rick James. There was no argument this year on Sinickal's pick as this was a consensus #1. Season 2 got off to a tremendous start and this was the best of the best! And as Pepster noted, we forget that Rashida Jones said no to anal in the love contract skit. Plausible?
2. Season 1, Episode 6 - Mad Real World. I mean, damn. Pepster's first pick produced some unbelievable jokes and quotable lines - "What's the square root of this apartment?" Pepster also commended the musical guest as an important part of the theme of the episode. Yes, that was David Broom from Real World New Orleans.
3. Season 1, Episode 1 - Clayton Bigsby. We all sat down to watch the premiere and we all came away thinking that Dave Chappelle had just broken television. A black, white supremacist?
4. Season 2, Episode 5 - True Hollywood Stories: Prince. Season 2 of Chappelle's Show was a television miracle. The week after Rick James, Charlie Murphy was telling stories about Prince. We also got some more of Negrodamus. Brilliant.
5. Season 2, Episode 12 - Wayne Brady. "I'm Wayne Brady, bitch!" This episode was beyond quotable.
6. Season 2, Episode 7 - World Series of Dice. This is the first episode in the list to have a stand out musical performance (Kanye West and Common) to go along with a great skit set in the Marcy Projects. Great episode top to bottom with Mooney on Movies.
7. Season 2, Episode 2 - The Niggar Family. I will simply say that I didn't think something like this could be put on television in 2004. Add in Negrodamus - "Everybody wanna be black, don't nobody wanna be black," Black Gallagher and DMX, and damn.
8. Season 2, Episode 1 - The Racial Draft. We still can't believe this was still on the board. Genius skit and a great R. Kelley joke.
9. Season 1, Episode 9 - Playa Haters Ball. The first real debate in the draft as Pepster thought this would go later in the draft. Sinickal felt that the primary skit was really strong. I mean, "She wears underwear with dickholes in them."
10. Season 1, Episode 2 - Tyrone Biggums at School. This pick recognizes the strength of the musical performance. This was Mos Def and it was spectacular.
11. Season 2, Episode 8 - Jury Duty. And Oprah Winfrey gets pregnant - "It's not what's gotten into me, it's what's gotten into Oprah. My seed, bitch!"
12 Season 1, Episode 12 - Trading Spouses. Sinickal had this much higher on the board than Pepster. Long debate went on with Pepster stating that this episode had Jalen Brown talent, but Jason Tatum closing ability. Sinickal loved the main skit.
13. Season 2, Episode 11 - Greatest Misses. Great musical performance by Kanye West, Freeway and Mos Def, and some unbelievable quotes including "You so dark that when you touch yourself it is black on black crime," and "She got one big tittie and one little tittie. They call that bitch Biggie Smalls."
14. Season 1, Episode 5 - Great Moments in Hook Up History. Pepster had this really high for Sinickal's liking. Pepster commented that this was for the Fat Joe musical performance and that "it came in higher than I thought, and I did my list."
15. Season 1, Episode 7 - Real Movies. Very different views on this episode. Liked much more by Pepster than Sinickal here.
16. Season 2, Episode 10 - Making the Band. Neither of us can believe this lasted this long. Great guests, and the Oscar the Grouch quote "I beat my dick like it owes me money."
17. Season 2, Episode 8 - I Know Black People. The quote from Sinickal on this lasting so long is that "we must have been drafting for need up until now."
18. Season 1, Episode 8 - Tyrone Bigum's Intervention. It is at this point of the draft that we both begin selecting for one aspect of the episode.
19. Season 2, Episode 6 - Internet as a Real Place. Also included what life would be like for Lil John which was hilarious.
20. Season 1, Episode 4 - Reparations. With Busta Rhymes as the musical guest, Pepster and Sinickal believe this episode was drafted exactly where it should have been at the end of the top 20.
The last seven episodes are:
21. Season 1, Episode 11 - Fisticuff: Turn My Headphones Up
22. Season 1, Episode 3 - Zapped
23. Season 3, Episode 3 - MTv Cribs
24. Season 1, Episode 10 - Piss on You Video
25. Season 2, Episode 12 - Black Bush
26. Season 2, Episode 3 - White People Dancing
27. Season 3, Episode 1 - Tupac is Still Alive
28. Season 3, Episode 2 - Black Howard Dean
I will close this post with this thought. Season 3 was awful, but this draft was a lot of fun. Can't wait to see what the next several hour waste of time produces.
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