DAR TV: The 10 Greatest Chappelle's Show Characters

By @TrueGodImmortal

Chappelle's Show is a national treasure in television history. In 2003, the inception of the show brought about a huge wave that turned Dave Chappelle from a top stand up comedian to a worldwide star. After season 1, Chappelle came back with a vengeance and took his show to an entirely different level with season 2. After the season 2 success, Chappelle decided to walk away from it all. Citing that the show was ruining his standup  due to hecklers and drunk patrons (and life in a way), it seemed as if Chappelle was searching for some form of peace of mind. While the show brought a gift and a curse to Chappelle, the audience was always enamored with sketch after sketch that he brought us. With Dave returning to the spotlight in 2017 due to his Netflix specials and his huge 1 month run at Radio City Music Hall, I thought what better way to pay homage to the genius of Chappelle than to look at the 10 greatest characters to come from his own brain. Let's get into it.

10. Tron
(Played By Chappelle)

-I thought about a number of things when I made this decision. Then, I went back and watched the Reparations skit, the Law and Order skit, and of course, Mad Real World, and I realized instantly that Tron was a classic Chappelle's Show character. I wanted to put Charlie Murphy's portrayal of Tariq in Mad Real World or even his portrayal as Buck Nasty on the list, but I just couldn't put them over Tron. I almost placed his Chappelle's portrayal of Puff Daddy on this list, because it's iconic, but much like the Wayne Brady skit, it was a one off classic sketch that carried over, but not as much as Prince or Rick James. This list is far from easy, but if you doubt Tron being included over the other possible choices, go back and watch the sketches he was in. Every time you see Tron, there's a quote (Katie has some big ass tit-tays) or a scene that will make you laugh (him pleading the FIF is still hilarious). Tron deserves more credit for his role.

9. Ashy Larry (Portrayed By Donnell Rawlings)

-Now, don't get me wrong. Ashy Larry is far from my personal favorite character. However, it became a cult favorite for many and Donnell Rawlings is still known to so many as Ashy Larry. That's a once in a lifetime character and if I asked you to name characters from the show, more than likely, after Tyrone Biggums, Rick James, Prince, and maybe another one or two on this list, Ashy Larry would come to mind. The rise of Ashy Larry came on the World Series of Dice sketch, and that sketch led to a career renaissance of sorts for Donnell, who utilized Ashy Larry to get to a higher position or at least more notoriety.

8. Black Bush
(Played By Chappelle)

-This is one spot that I debated over time and time again. When making these decisions, I thought of my personal preference for characters, the memes and gifs I see utilized the most from the show, but most of all, I look at the sketch and how hilarious it is and what it means to the show. In my opinion, the Black Bush sketch is a top 5 sketch in Chappelle's Show history, and it's full of quotable moments and even has some hilarious outtakes on the DVD. The beauty of the character is that Black Bush did literally whatever he wanted or saw fit, which was akin to the real George Bush in perception at least. If you doubt that Black Bush is one of the greatest characters from the show, I suggest going back and revisiting the sketch and checking for all the hilarity that the character presents (also, Mos Def was hilarious in the sketch as well).

7. Lil Jon
(Played by Chappelle)

-I wasn't as fond of this character but in terms of importance, it helped take Chappelle even more mainstream while giving him a bigger platform in essence. It wasn't even a great impression of Lil Jon, which makes it even funnier. It's a terrible dread wig under an oversized fitted hat and the standard shades that Lil Jon wore at the time, coupled with the catchphrases he belted out often to the world. Whether it was "Yeah", "Okay", or "What", Chappelle made Lil Jon seem more hilarious by design and when he went into his routine of talking regularly as Jon, it was even funnier because of Lil Jon's real voice. The fact remains, although Lil Jon was not one of my favorites, he was easily one of the greatest Chappelle's Show characters.

6. Leonard Washington
(Played By Chappelle)

-Hands down, the most underrated character in Chappelle's Show history. Every other character on this list I see people discuss very often, but there is no character quite like Leonard Washington. Period. Aggressive, loud, but always ridiculously hilarious, Leonard makes his debut on the season finale of season 1 on the Trading Spouses sketch, and that honestly might be one of the funniest sketches of the show's history. The way Leonard talks makes for a hilarious back and forth with his "new" spouse (a white woman) and his "new" son (a white kid who listens to G-Unit and wants to be street), and when he talks to the camera, he gives us quotes for days. My favorite Leonard Washington moment? Aside from mistaking a sexual object for a lightsaber, it would have to be his appearance in the World Series of Dice sketch. That whole sketch is hilarious, but Leonard Washington is the highlight of it. He really is an unsung hero of the show.

5. Silky Johnson
(Played by Chappelle)

-This is strictly a personal choice. Sure, many know Silky Johnson and the Playas Hater Ball, but they don't understand how vital this dialogue from the sketches he was a part of are. For instance, the outtakes on the DVD show Chappelle hilariously roasting as Silky and just saying the most outlandish shit you could think of, which is why I love Silky Johnson. From the way Chappelle uses the voice, the mannerisms, and most of all, the quotes to make you laugh, you knew you were watching something special. From his joke about Rosie O'Donnell wearing underwear with dick holes in them (classic) to his hilarious duty to go home and put some water in Buck Nasty's mother's dish to his roasting of the jheri curl sporting Beautiful, Silky was on fire and he wouldn't let up. Honestly, he might be my personal favorite character on the show next to Leonard Washington. Silky Johnson is Playa Hater Of The Year and one of the greatest characters in the history of the show.

4. Prince
(Played by Chappelle)

-There are many people and comedians who have played the role of Prince throughout their careers on sketch comedy shows, but there could be no one who did it as great as Chappelle. It wasn't that he looked exactly like Prince. Or that he talked similar. It was the storytelling and the narrative behind it. Prince playing basketball wearing a blouse. Prince cooking pancakes. Everything about this sketch was hilarious and I think it's probably the 2nd or 3rd greatest sketch of all time on the show. It's honestly just as important as the Rick James character because every time I saw Prince, there was a part of me that thought to the sketch. That's the mark of a truly classic character and sketch.

3. Clayton Bigsby
(Played by Chappelle)

-I remember watching this on the first episode of the show and laughing my ass off. I was surprised that Chappelle pulled this off and made it classic, and this is honestly one of those characters that was a risky hit or miss when executing. Luckily, Clayton Bigsby, the black white supremacist didn't disappoint and was sincerely laugh out loud funny. From his description of Jewish people, Arabs, and of course black people to the moment it's revealed he's black (to himself), it is absolutely a hilarious trip. It's the sketch that put Chappelle on the map, and it's the one that showed that he could tackle heavy topics and still make everyone laugh at unconventional comedy.

2. Tyrone Biggums
(Played By Chappelle)

-Never in my life would I have imagined that a crackhead character would become this iconic. I still can't process it. In terms of television history, Tyrone Biggums is a legend. The name itself is hilarious. The way he talks is hilarious and every single appearance on the show from the time he went to speak to a local school to the attempted intervention all the way to his hilarious appearance on Fear Factor with Joe Rogan was completely hilarious. Tyrone Biggums is silly comedy at its finest and the character is iconic for so many reasons that there's no way this character doesn't make the top 3 of any Chappelle's list. To be honest, it could very well have a case for no. 1 because it's an original character. Looking for more reasons to acknowledge the greatness of Chappelle and his genius? Look no further than this character.

1. Rick James
(Played By Chappelle)

-Now, this isn't a character necessarily, but the portrayal of Rick James by Dave is hilarious and honestly the greatest thing about the show. It remains the biggest piece of the show's legacy surprisingly, and for good reason. Much credit has to be given to Charlie Murphy who tells the True Hollywood Story to perfection, and if he wasn't playing himself, he would be a top 3 character for this. Still, Chappelle took the role and made it something special, with the over the top mannerisms, the multiple quotes, and much more. There is no character in the history of the Chappelle's Show more important than the portrayal of Rick James by Dave. There was no way I could put anything above his portrayal of Rick James. At all. Darkness, feet on your couch, I'm Rick James bitch, what did the five fingers say to the face, and so much more.... this is the greatest character in the show's history. Bar none.

-True