LegenDARy Comedians: Dave Chappelle

Introduction By @TrueGodImmortal
-Dave Chappelle is an enigma. He's a legend. He's quite possibly the greatest comedian of all time based on his life and what he's accomplished and stands for as well. His rise to the top was a long one, yet it happened all so quickly, that it almost felt like it didn't happen. Chappelle started off as a kid in the comedy clubs, but his first real break to me came from his small role as a comedian in the Nutty Professor. I was in tears laughing at his role there and knew that he would be something big, but no one could ever guess how big. When I first saw his Killing Them Softly standup, I was captivated.

While not the biggest fan of the film Half Baked, that's what truly boosted his profile in some way. I think the idea of Chappelle as a weed loving, honestly raw comedian is what made him so appealing, and his mannerisms were flawless and his comedic timing impeccable. In standup, Chappelle is poised, never running the joke in the hole, never overdoing it, but just keeping it perfectly aligned to have the audience in stitches. From his bit about a baby left out on streets to his honest segment about women who "dress the part of whores", Chappelle engaged the audience in a way that flowed amazingly. His Showtime standup would also leave me in tears, from his bit about Grape Drink vs Grape Juice (nigga, what the fuck is juice.... I want some Apple Drink... it's green).

What sticks out when people think of Chappelle of course is his Comedy Central show, Chappelle's Show, and rightfully so. It was masterful. From every skit to the musical guests, Chappelle's Show is one of my top 5 favorite shows of all time. In two short seasons, Chappelle captivated America with his look at Clayton Bigsby, Tyrone Biggums, The MAD Real World, Fisticuffs, Trading Spouses, The Player Haters Ball, R. Kelly and his musical talents (ha), Samuel Jackson Beer, Wayne Brady, the late great Prince and Rick James, and the list goes on. Each episode was a classic moment happening and Chappelle's Show is truly a blessing to have witnessed and lived through. The sketches are the epitome of timeless and are still as funny as I remembered them being from the start. While the skits and the show itself lived in infamy, what also lived in infamy was Chappelle walking away from the show and a 50 million plus contract for various reasons. While we will never know the real reasons, Dave has speculated and spoke about why he left and chose to walk away, and it seemed it all boiled down to one big thing: integrity. Integrity was essentially what makes Chappelle so special, as a comedian, as a part of the Hollywood scene, and as a man period. Today, we talk one of the greatest comedians ever, and the most powerful comedian of the 2000s.

Dave Chappelle is one of the greatest stand-up comedians ever and one of the greatest comedians ever period. One of the most striking things about his comedy is his ability to see things before they happen and comment so accurately on them, that it was almost scary how on the nose he was. More than that, he touched on things that no one would ever think to do on TV, let alone even speak about. Starting the first episode of the first season of his show with the iconic Blind Black White Supremacist Clayton Bigsby sketch was a perfect example of what Chappelle had in the chamber and he wasn't done firing. From there we got skits like ''The Niggar Family'', ''Black Bush'', The underrated ''Real Movies'' skits, ''Getting Oprah Pregnant''...I could go on and on, but the most iconic of all these skits have to be his ''Charlie Murphy: True Hollywood Stories''. Dave Chappelle taps Eddie Murphy's brother Charlie to share his incredibly wild stories of hanging out with two icons in Rick James and Prince.

Starting with the Rick James story, we got Chappelle playing Rick James and acting out every moment of Charlie's completely ridiculous but somehow true story and with it, we got some of the greatest moments of the show's entire run. From finding out what the five fingers said to the face, to UNITY being imprinted in Charlie Murphy's black forehead for weeks to the now iconic line 'I'm Rick James BITCH', (a line that the actual Rick James dropped at the BET Awards shortly before his death, further adding to its legend.) Chappelle gave us one of the greatest skits in TV history. What makes it even better is that Chappelle had never met Rick James, and everyone that actually knew the man could attest to the accuracy of his portrayal, to the point where Chappelle was actually rumored to play him in a biopic.

So what do you do to top Rick James? You bring Charlie Murphy back the NEXT episode to tell a story about playing basketball with one of the greatest artists of all time...Prince. This to me is the better of the two skits, as Charlie weaves a tale of challenging Prince to a game of basketball and getting his ass handed to him. Despite this being the best of the two, I wouldn't have placed this above Rick James in terms of impact until recently. Prince actually used the picture of Chappelle playing him as a cover for his single, and since his death, the skit has been viewed over 600,000 times. On top of all that, a picture recently surfaced of Prince standing over Charlie Murphy having beaten him at basketball and anyone who saw it IMMEDIATELY knew what it was, years after the skit itself had been released.

In addition to tackling real life figures, Chappelle had a real talent for bringing completely original characters to life and making them iconic on their own. Two of my favorite characters in the entire show's run are Chappelle's player hater, Silky Johnson and the GAWD Leonard Washington (Where I'm from? A little town called Nunya Gotdamn Bidness..Let's play some dice bitches). Chappelle's ability to make these characters stand on their own is what truly gave this show life. A show can't live off of celebrity impersonations alone and Chappelle knew that.

From his classic stand-up specials to the iconic ''Chappelle's Show'', his mark has been made on pop culture and will stand the test of time.

“The Kid”, a nickname given to Dave Chappelle by legendary comedian/actress Whoopi Goldberg back in 1992 while he was still doing standup skits on amateur night at the Apollo in Harlem. I think it’s a sign of talent and potential when you can get noticed by legends within your field and Chappelle did just that. For several years afterwards, he would pick up minor roles in films and create several show pilots that would never come to fruition, until the early 2000s.

It was January 2003 when Chappelle was picked up by Comedy Central and aired his extremely hilarious and highly popular “Chappelle’s Show”, and it was an instant hit. I think the only complaint would be that it didn’t air for long enough. What made this so successful is simply the unapologetic humor. He addresses much of the same topics and uses a similar approach to comedians before him, but what makes Chappelle so different is, it came to him so naturally, he was instantaneous in his popularity and somehow connected to every demographic. In 3 seasons, Chappelle was able to do what Richard Pryor did in 10. He perfected impersonations, he targeted every race and even addressed corporate moguls and music icons...like I said, he was  “unapologetic”.

I don’t have a favorite when it comes to this guy because everything and anything Chappelle chooses to target is filled with hilarity. He’s also the king of signature punchlines. Things that Chappelle has referenced or said have caught on more than any comedian before him and are STILL as funny and relevant as they were years ago. I don’t think you can even hear the name Rick James without immediately wanting to say “I’m Rick James Bitch” (or having someone else chime in with it.) or “I’m Wayne Brady Bitch”. Other dope moments include having Lil Jon on the show while Chappelle is impersonating him, as that was the funniest back and forth ever.  And of course, the “Charlie Murphy’s True Hollywood Stories”, which would become historic. I also thoroughly appreciate his making fun of Puffy and “Making The Band”  Like I said, there’s no way you can pick a favorite or even rank them, all his skits are beyond hilarious.

Dave Chappelle’s humor is definitely not for everyone, it’s crude, can be offensive, and is the essence of unfiltered. He’s the only comedian/actor I’ve known of to say things or do things regardless of media backlash. It’s not often we get to experience someone’s perspective and opinions on social issues in such a humorous way. Chappelle is one of those people who no matter what, will always remain a comedy legend and it speaks volumes to his talent and abilities that he was able to achieve this reputability in a fraction of the time it would take comedians before him. He will forever be regarded as one of the best.

Throughout Dave Chappelle’s career, one thing remained a constant, he kept true to what he felt was right. Towards the height of Chappelle’s run with the critically acclaimed “Chappelle’s Show”, he felt himself reaching towards a level of celebrity to which he and his family would not be able to feel comfortable, and rightfully so. In his interview with James Lipton on “Inside the Actors Studio”, Chappelle describes how making millions of dollars messes with those celebrities in a position where their privacy is out in the open. Chappelle has always been a rather secluded individual, preferring a more rural area than city life, so the thought of being in the public eye 24/7 must have been intimidating. While the career of Dave Chappelle may not be fully over, at this point he has already reached the peak of his career, which is why most fans look at him like a legend and reminisce on the old sketches they know and love.

So, it's come to this. We're finally talking Dave Chappelle as a whole on this here website. That's cool. I'm ready for it. I first came across Dave Chappelle in his early moments,  unlike a lot of his fanbase. Instead of, like, in The Nutty Professor or his VERY VERY early standup moments, I saw him first in Robin Hood: Men in Tights. While the movie itself wasn't all that great (had its moments, but overall, it was kind of sloppy), I always remember Chappelle (mainly because he was "the Black guy," Ahchoo).

From there, we watched him have a few bit roles here and there and then crack into the mainstream with his role in The Nutty Professor, pretty much playing an exaggerated version of himself. We fell in love with (and wanted to slap the shit out of) him in this role, as he was hilarious, but you're kind of supposed to cheer for Professor Klump to, you know, not take the BS and just manhandle him (which he does as Buddy Love). After Nutty and an HBO special (go peep it, if you can find it), we got quite possibly one of the greatest stoner comedies ever made.

Half Baked.

Now, this flick showed us that Chappelle had comedic timing outside of just being Dave Chappelle. If you've never seen it, do so (if only to see Huck from Scandal do the "fuck you, fuck you, fuck you--you, you're cool--fuck you" scene). You'll thank me later, mainly because you don't need to be blitzed out of your mind to love this flick. It's crazy as hell, but it all makes sense within the realm of the story's world. You know what, fuck it. You could give me the panel to talk about Half Baked for hours. But, I won't do that to you. Just...go see it if you haven't.

Afterwards, we got Killing Them Softly. This comedy special is classic. It shows Chappelle at his best, just straight up going in on, well, everything. At one point, it was one of the few comedy specials I legitimately owned myself. However, looking back on Undercover Brother, I'm not as big of a fan of his "Conspiracy Brother" portrayal as I was when the movie came out. Perhaps it's because I now know he's so much better, even within a PG-13 setting, at racial commentary and satire.

...Thankfully, we got Chappelle's Show for our troubles. Key & Peele owe their success to this one. Sorry for possibly overstating its importance, but it's needed. It was a series that was smart while still being LMFAO funny. Plus, it helped make CHAAAALEEE MUHHHPHY into a household name. We got classic skits like Prince balling, Rick James, Clayton Bixby, The Race Draft, and so on. But, somewhere along the way, Chappelle realized that some people weren't laughing with him on these racially-charged commentaries...instead, they were laughing at him (and/or just being kind of dense to what he was doing). So, we got the sabbatical.

Recently, it seems that Chappelle's been kind of a victim of his own success. I mean, he still deals with people spouting off Chappelle's Show quotes when he's trying to put on shows. He's still hilarious, still doing things to benefit society, he even got The Fugees to reunite for a hot second during his Dave Chappelle's Block Party concert film. Overall, Chappelle is a genius. A great. A man who shouldn't just be regulated to being known for coming up with the quote "fuck yo' couch! Buy another one, ya rich mothafucka." So, if you're a fan of his, check out all his work. You'll thank me later (and I think that's becoming a wack-ass catchphrase of mine. Ah well, fuck it).

Outro By @TrueGodImmortal
-Some comedians stand the test of time. Chappelle is one of them. With his talent, ability, and his honesty in his comedy, he is a rare breed. He remains as hilarious as he was before, and seems ready for a comeback after many public appearances, a ton of standup shows, and an appearance in the Spike Lee film Chiraq. Could Chappelle be on the way back? If anything, his honest commentary and comedic timing are needed in such an overly sensitive society. Perhaps he doesn't want to make make a full fledged comeback, but Chappelle will always be welcomed back by fans with much adoration and appreciation. It's a perk of being one of the greatest.



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