DAR Comedy: Rating Dave Chappelle's Stand-Ups

By @TrueGodImmortal

For many, Dave Chappelle is one of the most hilarious comedians of all time. For me, he is the greatest of our era and my personal favorite period. The way he constructs his jokes, the verbiage he uses, and his comedic style makes him beyond every other comedian of our time. With a knack for social awareness, honesty, and being as raw as possible, Chappelle came to even bigger prominence through his own Chappelle's Show before taking an industry induced hiatus. While the hiatus might have broken any lesser comedian, it seems as if Chappelle's hiatus gave him newfound life and perspective. After years away, Chappelle returned officially in 2017, dropping four specials through a mega deal with Netflix. With four new specials in 2017 to go along with the other three existing specials that he has, I wanted to take a look at them all and rate them one by one. Does Chappelle have a perfect standup? Does he have any misses? Let's take a look.

*HBO Comedy Half Hour: Dave Chappelle (1998)

-This is essentially not as important as the rest of his standup specials but it is noteworthy. Two years before his big standup comedic special breakthrough, Chappelle would discuss a number of situations that brought the audience laughter, but the most infamous piece of the special to me was his discussion on doing shrooms. Through the roughly 30 minute special, Chappelle shows he was still trying to find his footing as a comedian, but he had enough here to delight the audience, but it doesn't warrant many rewatches. Still, if you've never watched this one, take 30 minutes out of your day and give it a watch (I advise binge watching all of the Chappelle specials).
Rating: 6.5/10

*Dave Chappelle: Killin Them Softly (2000)

-This was the special that made me a full blown Chappelle fan. I had seen Chappelle in Half Baked, and while that was funny enough, when I heard about this special, I decided to give it a watch and I wasn't disappointed at all. This might be my favorite Chappelle special in general, or at least top 3, but the fact remains that Chappelle is in rare form here. One thing that will always be great about Chappelle is his ability to navigate through the audience and their tastes and determine what they enjoy laughing at the most. It's a rare trait that most comedians don't possess, but watching him tell the stories he tells in front of the audience showcases his genius. Whether he's discussing police brutality and how they used to sprinkle crack to plant evidence (among other issues) or even discussing how taking some responsibility for how you carry yourself can work wonders ("just because I am dressed this way..."), Chappelle controls the crowd and engages every viewer with his comedic prowess. There's not a single dry moment through this special, and honestly, up until recently, this was by far my favorite Chappelle special, but as you'll learn later in this article, Dave has given himself some more competition for his no. 1 standup. All in all, this is essentially the true making of Chappelle into the all time genius and legend that he was destined to become. If anything, this special is important for what it would begin, which is essentially the coming of age of Dave Chappelle.
Rating: 9/10

*Dave Chappelle: For What It's Worth (2004)

-At the height of his popularity, Chappelle would give Showtime quite possibly the biggest standup they would ever have. With a huge deal behind it, the funniest man in America at the time would set up a show in San Francisco at the Fillmore and deliver some of the more iconic jokes of our time. Honestly, I find this one to be a bit boring in spurts, which is in no way dismissing how hilarious it is, but there are a few dry moments here, which can be expected, but when the special is funny, it is laugh out loud, hold your side funny. Whether he talks about the amazement of learning what Grape Juice meant and how vital Grape Drink is (sugar, water, purple), or even detailing how the media overvalued the opinion of celebrities on matters that they don't really affect (where is Ja?), Chappelle coasts through the standup and that might be the only knock against it. He coasts so much here that some of the jokes hit hard and some don't hit as hard as they could have if delivered in the classic Chappelle way. Blame the drama surrounding Comedy Central, or even the fatigue of having to write his show at the time, but this special is just really good... instead of being truly great. The fact that a special being really good and not truly great is a slight knock against Chappelle further shows how amazing his career has been and how deep his genius is.
Rating: 7.5/10

*Dave Chappelle: Deep In The Heart Of Texas (2015)

-Taped at Austin City Limits, part 2 of his two special Netflix collection is actually older than part 1. Released in March 2017, this was taped back in 2015 and somehow.... it still felt fresh two years later. Often times, we see a comedy special that has aged a few years and the jokes are only topical for the time. That is not the case here. Chappelle details a number of experiences as only he can, and even manages to throw out a joke that is somehow related to the term "pussy juice", which shouldn't be as funny as it is, but his timing and delivery sell it like always. He discusses his moments as a parent and a husband in hilarious fashion, and even makes time to throw some random Lil Wayne references and jokes in to drive it home. Considering when this was shot one has to appreciate the way Chappelle commands the crowd, addresses the tougher topics, and most of all, delivers an outstanding show. Chappelle might be the greatest standup comedian ever, and the Netflix series of specials definitely will crown him as such, and get this, this is probably the weakest of all four, and it's great! 

Rating: 8/10

*Dave Chappelle- The Age Of Spin (2016)

-While many attempted to discredit this special, it is the more hilarious of the two released earlier in 2017. Taped out in California in 2016, this special is the funnier of the two that dropped in March, and I debated this personally for a while. I loved both, but I couldn't figure out which I preferred at the time. Honestly, the reason why this takes the cake to me is because Chappelle seems more comfortable than ever in this special, owning the stage and controlling the crowd. The special has a hilarious reoccurring joke about the four times that Dave has met O.J. Simpson, and the way he times each reference is perfect. Along with that, he also talks about the Bill Cosby situation at the time and of course, with the transgender community such a hot topic at the time, he touches on that whole issue with an honesty and realness that most comedians would be scared to do. Everything about this special is vintage Chappelle, and it was a sign that not only was he back, he might be better than ever. We would have to wait and see if that would be the case with his final two Netflix specials, but this was a great start for sure.
Rating: 8.5/10

*Dave Chappelle: Equanimity (2017)

-Yes, this special is only a day old at this point, but I've watched it twice and will do so a third time later. Shot in Washington D.C. during his epic run in September 2017, this special is Dave at his best once again, perhaps the funniest he has ever been. It starts off strong with Dave championing himself ("I'm dope nigga!"), and he goes through an hour of stories about his experience at a white friend's house for the first time while being poor to his experience seeing the faces of poor Trump voters and their ideologies, as well as looking at this sensitive world and calling it out for what it is. He makes jokes about everyone, as comedians have always, and delivers what might be the most hilarious take on Bruce Jenner and his "change" over. Along with a hilarious and random Draymond Green reference among other moments, Chappelle really owns the stage as only he can. He hints at taking a break from comedy and leaving it all behind again due to the sensitive climate, but one would hope he doesn't. If anything, in this era, a voice like Chappelle is needed and that becomes more evident as the days go by. He can offend many, he can be socially aware, he can discuss politics, he can do it all as a comedian and that's exactly what he does with Equanimity. This is almost like Dave getting a practice shootaround in before going into the game to drop 50 points, as this is just about as flawless of a standup special as they come. You could watch this and think "there is no way Dave would be able to top this ever", and as I watched this for the first time, I thought this as well. Little did I know.....
Rating: 9/10

*Dave Chappelle: The Bird Revelation (2017)

-Between the two new specials, I find this one to be the smarter and more raw of the two. Taped in front of a more intimate audience in LA just a month or so ago, Chappelle weaves between the current sexual assault cases with comedy that doesn't disrespect any victims, but also speaks to the "buyer's remorse" aspect of some of these allegations. The truth be told, this might be the most brilliant standup of all time, as Chappelle speaks to the Kaepernick kneeling situation, referencing Michael Jackson and R. Kelly again, while ending with one of the most genius stories in all of comedy. He ends the set with a reference of the Iceberg Slim book "Pimp", and he ties in a story in that book with his own story of why he left for Africa, and it closes out the special stronger than any other on the list. If this is the last special from Chappelle for a long time, he went out with a bang. This is quite possibly his absolute best work, and he manages to never hit a dry spot and mixes enough bold comedy in with true wisdom and amazing analogies. The Bird Revelation might be the greatest moment in Chappelle's comedic career and his perfect show. Give it a watch ASAP, you won't be disappointed.
Rating: 10/10

-True