10 Best Dave Chappelle Stand-Up Performances, Ranked

Summary Dave Chappelle's stand-up specials cover a wide range of tones, tackling absurd topics, topical issues, and serious matters with ease.

His fearless performances like 8:46 and The Closer address racism and LGBTQ+ topics controversially, showcasing his commanding presence on stage.

Chappelle's earlier specials like Killin' Them Softly and Equanimity highlight his masterful storytelling and ability to push comedic boundaries.

Content Warning: The following article contains misogynistic language and discussions of transphobia, racism, and gun violence.

Taking a look at all of the Dave Chappelle stand-up specials, it is easy to see how he has become one of the most popular stand-up comedians of his time as well as one of the most controversial. Chappelle has a unique ability in his stand-up specials to tackle any tone he feels is necessary for his performances. He can joke about the most absurd topics, offer his unfiltered opinion of topical issues, and even forego jokes altogether to speak from the heart about serious issues.

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, Chappelle has established himself as a voice without equal in the world of stand-up comedians. With his specials ranging from the silly pre-Chappelle's Show era to the more controversial recent specials, taking a look at his work on stage highlights his amazing career.

Related 20 Best Stand Up Comedy Specials From Bo Burnham to Richard Pryor, these stand up specials stand the test of time.

10 Deep In The Heart Of Texas (2017)

Runtime: 1h 6m

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Also known as Dave Chappelle: Live at Austin City Limits. This Netflix stand-up 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 is another fearless stand-up performance from Chappelle as he unapologetically tackles serious topics like racially motivated police shootings and the threat of ISIS in a thought-provoking and hilarious way. Interestingly, the special was filmed years before it was released, leading to a number of bits that felt oddly dated. However, along with his other special from 2017 titled The Age of Spin, Chappelle won a Grammy for the special.

9 The Age Of Spin (2017)

Runtime: 1h 7m

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. It was a more polished and energetic performance that continued to signal his comeback. 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. Given that audiences have been watching Chappelle perform as the beloved comedian for years, it is interesting to see him acknowledging that he is feeling out of touch but turning it into more funny material. However, the highlight of the special is Chappelle's description of his various run-ins with O.J. Simpson.

8 8:46 (2020)

Runtime: 27m

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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 the 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. Though Chappelle's opinions can often cause controversy, this is a perfect example of how commanding, intelligent, and powerful he can be while on stage, regardless of how many laughs he is getting.

7 The Closer (2021)

Runtime: 1h 12m

The Closer marked the final installment in a string of stand-up specials for Netflix that helped reintroduce Chappelle as a comedy juggernaut while also courting plenty of controversy. 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 the perceived 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. The special is a mix of the complicated aspects of Chappelle's most recent specials, hilarious and clever bits mixed with ugly observations that feel as though the comedian is espousing personal opinions against others. Overall, it makes The Closer an intriguing yet uncomfortable experience.

6 What's In A Name (2022)

Runtime: 39m

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 while going on to explain what he thinks those ideals mean.

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. What makes the special so fascinating is how complicated it is and how much Chappelle comes off as a flawed person. He is not doing bits but rather sharing his own views. Some will find a lot of truth in what he says while others will see him as stubborn and closeminded, but it is compelling to see him perform in any case.

5 Equanimity (2017)

Runtime: 1h 3m

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Equanimity was Chappelle's final 2017 Netflix special. It was just as hilarious as the others and also a bit lighter while being less controversial. Echoing Chappelle's classic, outrageous stand-up style from the Chappelle's Show 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 total control of the audience, he takes them through his childhood and his experiences with "fake news" and backlash from the transgender community. Equanimity is a gut-busting performance that emphasizes the comedian's wits and talent, as well as his bold take on subjects that will not sit well with all audiences. The special won Chappelle an Emmy for Outstanding Variety Special (Pre-Recorded) as well as the Grammy for Best Comedy Album.

4 Sticks And Stones (2019)

Runtime: 1h 5m

Sticks and Stones was Chappelle's return to Netflix following a short break following his special Equanimity. However, the time away from the stage did not dampen Chappelle's ability to be controversial in any way as this proved to be his most divisive special to date. Sticks and Stones appears to be courting such a reaction as Chappelle tackles such subjects as celebrity abuse scandals and the LGBTQ+ community which Chappelle controversially referred to as "alphabet people".

This is one of the hardest specials to reconcile for fans of the comedian as it displays his brilliant and fearless comedy style while also seeing him making some tone-deaf comments that are, at best edgy, for the sake of being edgy and, at worst, are hateful speech on a massive platform. However, Chappelle also makes himself a willing target by refusing to cater to any audience with his comedy.

3 For What It's Worth (2004)

Runtime: 1h

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 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, but Chappelle still came to this special like a man with something to prove.

It is interesting to look back at his older sets how, seeing the difference between the confident and perhaps arrogant comedian he is today, and the hungry and scrappy comedian he was then. It is hard not to enjoy the older version more as Chappelle has a terrific energy and wackiness that was replaced with self-seriousness later on. It is also a more intimate set with a crowd of little more than 100 people, yet Chappelle commands the room nonetheless.

2 Chappelle's Show (2003 - 2006)

Runtime: 22m episodes

There's a reason why Chappelle's Show is popular and 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. It was also fun seeing Chappelle comment on the sketches before and after they aired, giving some insight into how his stand-up comedy joke writing gave way to sketch comedy writing.

1 Killin' Them Softly (2000)

Runtime: 57m

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 powerhouse 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, Chappelle had 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.