What are the best controversial on-stage discussions about cultural norms and shifts, along with enlightening commentaries about his perception of the world around him.
In pop culture, Chappelle is perhaps best known for his Comedy Central series Saturday Night Live in November 2016, and subsequently signed a lucrative stand-up deal with Netflix just days later.
Chappelle fully understands that provocation leads to truth onstage. The comic's jokes may feel inappropriate or offensive to some, but they usually thematically connect to his life experiences as a Black man living in America. As a result, perspective and context always matters when breaking down Chappelle's routines. In recent years, he's become even more comedically aggressive with his material, presumably because sociopolitical topics from his early acts remain painfully relevant in the present. Here are the four stand-up specials that every Chappelle fan should watch.
Killin' Them Softly (2000)
In 2000, the Half Baked, but was more of a recognizable face than a well-known actor. With Killin' Them Softly, Chappelle takes the stage in his native Washington D.C. and focuses heavily on the differences between Black and white people. The classic set includes a story about his white friend Chip getting high and politely conversing with New York City police, with the punchlines often linking to observational humor. The comic also breaks down inner city culture with a bit that thematically connects to previous jokes about questionable investigative techniques by police officers.
Whereas the first half of Killin' Them Softly includes the best jokes, the second half foreshadows the future of American politics. Chappelle muses about the first Black U.S. president being elected — approximately eight years before Barack Obama reached the Oval Office — and later jokes about about how white people don't like discussing who they voted for: a concept that took on a new meaning when Obama's tenure ended and Donald Trump's presidency began. Overall, Killin' Them Softly remains such a classic because of Chappelle's comedic structure. He incorporates side characters throughout the act, and repeatedly returns to certain one-liners from earlier in the show. The special reveals that Chappelle has plenty to say about American culture, but also suggests that he's more interested in entertaining the audience than provoking them, at least at this point in his career.
The Age Of Spin (2017)
The Age of Spin marks Chappelle's first Los Angeles show in a decade, and benefits from his old school approach. For example, the comic doesn't show the ego that's prevalent in another 2017 special, Equanamity, and he doesn't include any didactic commentaries about the art of stand-up comedy — a trend that would become a centerpiece for several 2020 Netflix specials (see those by Chris D'Elia, Jim Jeffries, and Kevin Hart, to name a few). Structurally, Chappelle disperses four stories about meeting O.J. Simpson, and also drops several pop culture references, from Making a Murderer to Key & Peele, from Bill Cosby to Kevin Hart. In the special, Chappelle engages with the audience by referencing familiar names, but then challenges them through various bits about gender and sexual assault.
In retrospect, The Age of Spin serves a reminder that Chappelle is always consistent with his comedic approach. The special's title applies to both modern politics and social media, which creates an interesting dynamic as Chappelle discusses the concept of "comparative suffering." He's clearly annoyed by cancel culture, but also seems to recognize an opportunity for shared reflection about the not-so-distant past. When Chappelle recalls the Care Bears from the '80s and states that "We were trained to care," he seems to genuinely believe that maybe the world will slow down a bit. And it's that sense of uncertainty about the future that drives the act as a whole, even if Chappelle knows exactly who he is as a person, and as a performer.
Equanimity (2017)
With Equanimity, Chappelle delivers another classic routine but seems more self-aware than ever. Just as he wore "Chappelle" clothing the year prior on Saturday Night Live, he does so again in the Netflix special and boasts about being a "dope" comic who is so good that he writes jokes backwards. Chappelle's bravado carries over into a commentary about cancel culture, with the comic stating "As a policy, I never feel bad about anything I say up here.”
This time around, Chappelle's routine is more predictable with provocative jokes about gender and cultural taboos, but his comedic timing is exceptional as always. In Equanimity, the comedian speaks unfavorably about "poor whites," a bit that carries over to his 2020 Saturday Night Live monologue after Joe Biden defeated Trump in the U.S. presidential election. By the end of the special, Chappelle jokes about "standing too close to the elephant," and how people can miss out on the bigger picture if they're too focused on one particular talking point. In that sense, Equanimity shouldn't be reduced to Chappelle's self-serving jokes or transgender-themed humor, but should rather be viewed as a larger message about identity, online culture, and self-reflection.
Sticks & Stones (2019)
In cancel culture topics head-on, the comic establishes a specific vibe for the show and subsequently cites examples about having his words misrepresented. There's a brilliant bit about Chappelle's Show and the power of language, along with a light-hearted commentary about the bizarre Jussie Smollett saga. From Chappelle's perspective, he only jokes about certain people or groups because he identifies with them in some form.
Chappelle breaks free from a formulaic structure in Sticks & Stones and takes aim at everybody, but not in a mean-spirited way. In the present, there's always the danger of comics investing too much time in cancel culture commentaries, but a polished and progressive comic like Chappelle knows how to make his point while linking together various themes. In this case, he provides personal anecdotes about celebrity culture, show business culture, and also Black culture to remind the audience about his unique perspective and how it relates to his material. Sticks & Stones on Netflix spotlights the decades-long evolution of Dave Chappelle, a comedian who seems genuinely invested in educating audiences about cultural truths that go overlooked.