Content Warning: The following article contains misogynistic language and discussions of transphobia, racism, and gun violence.
It is a fact that many of the best Dave Chappelle stand-up performances are also the most controversial. What separates Chappelle from other legendary stand-up comics at his level – such as Bill Burr or Chris Rock – is that Chappelle’s life itself is the crux of his style of stand-up. As sure as Chappelle has questionable views about sexual orientation and gender identity and expression, Chappelle himself is also undoubtedly an icon in the comedy industry.
After infamously walking away from Chappelle’s Show(and millions of dollars), living in South Africa for years, and returning to lambast tabloids that claimed he suffered from drug addiction and mental problems, Dave Chappelle has established himself as a voice without equal in the stand-up comedy world. Known for writing and performing Chappelle’s Show’s iconic sketches and the highly controversial 2021 Netflix stand-up special The Closer, pinning down Chappelle’s best stand-up sets is no easy task. However, based mostly on mainstream comedic potential alone, there are a few that stand out as Dave Chapelle stand-up comedy performances of all time.
10. Deep In The Heart Of Texas (2017)
Also known as Dave Chappelle: Live at Austin City Limits. This Netflix special aired in March 2017 and served as much-needed therapy as the world started to spin out of control. The performance addressed the rise of racism with a series of anecdotes concerning awkward interracial encounters, before moving on to parents of today and the growing list of celebrity scandals. Deep In The Heart Of Texas deserves a spot among the best Dave Chappelle stand-up performances and since he unapologetically tackles serious topics like racially motivated police shootings and the threat of ISIS in a thought-provoking and hilarious way, it’s a show that highlights how Chappelle is one of the funniest Black comedians of his generation.
9. The Age Of Spin (2017)
The Age Of Spin – a.k.a Dave Chappelle: Live At The Hollywood Palladium – was released alongside Deep In The Heart Of Texas and featured a more focused take on similar grounds. After addressing the mounting problems caused by his own generation, he holds a mirror up to the next, lest they end up crafting a similar hell for themselves. The performance featured meditations on the rapid evolution of humanity and technology and his struggle to keep up, as well as his go-to icebreaker O.J. Simpson.
8. 8:46 (2020)
Fans can’t be blamed for not knowing what to expect when Chappelle announced he would be doing a private outdoor show in June 2020. Just a few weeks after George Floyd’s tragic death and several months after the start of the pandemic, it was an uncertain and scary time. Chappelle acknowledges how strange the situation is during the slow start of his performance but quickly reminds everyone why Dave Chappelle’s Netflix special is called 8:46 – a reference to Floyd’s manner of death because of police brutality. It’s an unconventional stand-up performance, with more moments of jarring seriousness interspersed with jokes to punctuate the absurdity, fear, and anger around racism and gun violence.
7. The Closer (2021)
Dave Chappelle’s critique of the LGBTQ+ community and the way that social media reacts to his shows likely only added fuel to the growing fire about his brand of comedy. He doubles down and points out hypocrisy surrounding the “Me Too” movement, before defining himself as a proud feminist. Despite all of these audacious segments, the most powerful part of the special is undoubtedly his tear-jerking story about his friend and fellow comedian, Daphne Dorman. Inarguably one of the best Dave Chappelle stand-up performances, The Closer is also among Dave Chappelle’s most controversial specials.
6. What’s In A Name (2022)
Perhaps the most revealing recent work by Dave Chappelle, Netflix’s What’s In A Name is actually Chappelle giving a speech at his alma mater, the Duke Ellington School of the Arts, who decided to name their theater after the stand-up comic. Instead, citing the political outrage caused by his antics, Chappelle declined and instead opted to name the building the Theater for Artistic Freedom and Expression, saying that the school and community would decide if and when they’re comfortable naming the theater after Dave Chappelle. Apart from being a masterclass in storytelling, What’s In A Name’s arguably still problematic takes nonetheless seem to be genuinely driven by Chappelle’s intent to reconcile his views with audiences.
5. Equanimity (2017)
Equanimity was Chappelle’s final 2017 Netflix special. It was just as hilarious as the others and also a bit lighter and less controversial. Echoing Chappelle’s classic, outrageous stand-up style from the Chappelle’s Show series era, he begins by shamelessly bragging that he’s simply too good at comedy writing and performing, before masterfully demonstrating these skills with the flawless “kicked” routine. With the audience under his spell, he takes them through his childhood and his experiences with fake news and pissing off the transgender community. Equanimity counts among the best Dave Chappelle stand-up performances for its gut-busting performance that emphasizes the comedian’s wits and talent, leaving viewers crying from laughter all the way to its hilarious conclusion.
4. Sticks And Stones (2019)
After Equanimity, Chappelle took a short break after joking about being suspicious of his growing success. He returned with a bang in 2019 with one of the best Dave Chappelle stand-up performances in recent history. Ticking off every subject of controversy available, Chappelle took no prisoners. He even had a go at audiences, stating he’d perform more often if he wasn’t worried about getting ruined. While this special contains the infamously tone-deaf Dave Chappelle alphabet people rant, it is also modern Chappelle at his slickest.
3. For What It’s Worth (2004)
2004’s For What It’s Worth was Chappelle’s second official stand-up special, the long-awaited follow-up to his 2000 special with HBO. This full-length special aired on Showtime and was performed in front of a huge crowd at The Fillmore in San Francisco, during his TV show’s run. He had already mastered the art of stand-up and cemented his winning style by 2004, and as flawless as his modern routines are, his older routines where he actually had to try are among his greatest, and he works the auditorium as well as he works a crowd of 100 people as he goes into the intricacies of monkey-seduction.
2. Chappelle’s Show (2003 – 2006)
There’s a reason why Chappelle’s Show is streaming on Netflix two decades after it first aired. Even with the recent burst of Netflix specials, the greatest wealth of the best Dave Chappelle stand-up performances come from Chappelle’s Show, which ran for three seasons from 2003-2006. Along with many iconic sketches and parodies, Chappelle would open the show to a live audience at Austin’s Moody Theatre every week as America tuned in to get his unique perspective on things. Each one of Chappelle’s Show‘s hilarious stand-up comedy episodes brought something new and unexpected, pushing the boundaries of the genre and redefining it for years to come.
1. Killin’ Them Softly (2000)
After nailing his half-hour spot with HBO in 1998, they gave Dave Chappelle a full-length special in 2000. Killin’ Them Softly was a heroic comic performance for the time, with Chappelle working a multi-racial crowd before thoroughly exploring the more unspoken race divide without rubbing anyone’s nose in it. Even before Chappelle’s Show‘s Prince and Clayton Bigsby sketches catapulted him into mainstream stardom, Dave Chappelle already created one of the greatest stand-up specials at the turn of the century.
Despite being gone for years, Chappelle obviously hasn’t lost his quick wits and incredible ability to make taboo topics laughable. It would be easy to say it’s Chappelle at his best, but he continues to outdo himself. It’s only a matter of time before a new special dethrones Killin’ Them Softly as the best Dave Chappelle stand-up performance.
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