Ian Thomas Malone

dave chappelle Archive



December 2023



The Dreamer is a pathetic mess from a man who simply doesn’t care anymore

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The worst kinds of people to watch sports with are the ones who blame the officiating every single time their team gets blown out. The discourse surrounding the past few Dave Chappelle specials has essentially shifted from the comedic value of his work into a broader cultural discussion into the boundaries of the genre itself. Plenty of far-right publications took the non-sequitur route in their praise of Chappelle’s broadsides against the transgender community, lauding the bravery of his so-called “free speech” while casting aside any exploration of the merit of his humor.

The Dreamer is a lazy victory lap from a man with nothing else of value to offer the world beyond self-congratulatory musings on his own legacy, a lethargic effort aimed solely at fueling the far-right grievance industrial complex for another week. The Closer was a mostly humorless treatise centered around the backlash to his prior special Sticks and Stones. While Chappelle claims early on in The Dreamer that the controversy wasn’t worth the trouble, it’s kind of clear that it was, if only for one fairly sad reason. Trans jokes are pretty much all he’s got left.

After an opening bit where he compares trans people to Jim Carrey’s much-lampooned method acting work as Andy Kaufman in Man on the Moon, Chappelle mostly stays away from the trans community, though not without a clunk segue via some cheap jokes aimed at disabled people. There are some tasteless jokes aimed at the broader LGBTQ community, and a joke about identifying as a woman if he was sent to prison that falls in line with his previous special’s fascination with early 2000s style edgelord humor, but you can tell that Chappelle knows that his audience is growing tired of his obsession with gay people. A recurring theme throughout the special is Chappelle’s apparent level of self-awareness toward his reputation as a “lazy comedian.”

The most telling point of The Dreamer occurs halfway through when Chappelle starts on a bit about the Titan submersible. Chappelle admits that this joke never plays well on venues on his tour, but does it anyway, a joke that falls flat yet again at the Lincoln Theater in Washington DC. Longtime Chappelle director Stan Lathan does his subject no favors with constant cutaways to an audience that perpetually looks apathetic as joke after joke fails to land. It would be ridiculous to say that Chappelle doesn’t care what people think. His last two specials were entirely consumed with the reception of his work, at great expense to the comedic value of the material itself.

The DC location was ostensibly selected to draw parallels to Chappelle’s first special Killing Them Softly, also filmed at the Lincoln Theater, that propelled him to international stardom. The two decades that have passed since his debut have been kind to him in many ways, but an uncomfortable reality surfaces time and time again. He’s lost his edge.

Predictably, Chappelle spends a lot of time on the Will Smith slap endured by his friend Chris Rock at the Oscars, and on the spectator who attacked him at the Hollywood Bowl back in May. Chappelle squanders his unique perspective on the situation in favor of lazy jokes that lack the sharp timing that once defined his work. More and more, Chappelle just looks like a bored old rich guy out of touch with the industry he so radically helped define.

Comedy is not as kind to its aging stars as performers in other trades. The Rolling Stones can take the stage for two hours playing material that’s fifty years old. Chappelle can’t spend the night repeating bits from Killing Them Softly, even as his disengaged audience might wish that he would. There’s something fundamentally sad about watching Chappelle reflect on how hungry he used to be, while he tries to fill time in a special that often forgets that it’s supposed to be funny.

At times, Chappelle returns to his favorite punching bag, sprinkling a few trans jokes here and there, even as he pretends to claim that he gives people respect no matter what. He’s certainly resentful of the idea that people think he needs trans jokes to stay relevant, but not enough to do anything about it. There are enough shots at the trans community to ensure that the media will cover his new special, but the pickings are pretty thin otherwise.

The discourse that surrounded his last few specials will undoubtedly continue. People will spend the next few weeks playing armchair referee over the perceived boundaries of comedy. None of that matters.

The simple reality that Dave Chappelle’s newfound champions of the political right so conveniently ignore amidst the hornets’ nests that he loves to kick up is that the man has lost a step. The Dreamer isn’t particularly edgy. Instead, the special is something much sadder for a man who once sat at the top of the world. The Dreamer is boring.



October 2021



Preoccupied With Chappelle’s LGBTQ Grievances, The Closer Sacrifices Humor at the Altar of Cancel Culture

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The world has changed quite a lot since Dave Chappelle released his first Netflix special in 2017, further solidifying his status as one of the greatest comedians of all time. The concept known as “cancel culture” rode the wave of Trump’s perpetual victimhood, an attempt to preserve the communal status quo from efforts toward a more inclusive society. The free market, the same system that rewarded Chappelle’s ample talent with a $20 million-per-special price tag, now takes a more critical approach toward actions and language increasingly belonging to a bygone generation.

Dave Chappelle is the most successful comedian alive. That notion might be lost on a viewer of his latest special The Closer, an hour that largely abandons the pretext of comedy in favor of a litany of grievances, many toward the LGBTQ community more broadly, with a special emphasis on his seemingly favorite punching bag, the transgender community, or “transgenders” as he puts it.

Much of The Closer focuses on Chappelle grappling with the concept of empathy. He has plenty for disgruntled rapper DaBaby, widely condemned for homophobic remarks on stage in August 2021, which led to booking cancellations. Chappelle makes an interesting point that DaBaby’s career faced no hurdles after the rapper shot a man in Walmart, implying that homophobic jokes are a bigger offense than murder. The media’s selective sense of outrage isn’t really his target though.

Instead, Chappelle spends much of The Closer building an outlandish case that LGBTQ people possess a set of special privileges that people like DaBaby, J.K. Rowling, Kevin Hart, and himself do not. He suggests a kind of cozy relationship between the police and white gays, putting aside the well-documented history of homophobia within law enforcement. He laughs as he says he’s jealous of the gay community, reinforcing bits from Sticks & Stones, spending an entire special complaining that he can’t make jokes about gays as he makes jokes about gays.

Chappelle presents a similar case against Hollywood’s role in the #MeToo movement, highlighting events of performative allyship such as the all-black attire for the 2018 Golden Globes. He’s not wrong to suggest that the women who donned black dresses could have made bigger impacts by dismantling the industry’s power structure, but his conclusions bend over backward to toss the baby out with the bathwater. It’s a convenient manufactured either/or scenario, one beneath a man of Chappelle’s ample wit.

It’s hard to look past the intellectual dishonesty of Chappelle repeatedly insisting he’s not transphobic, even as he compares trans women to blackface, defends TERFs, and misrepresents Rowling’s long history of anti-trans sentiments. He puts the entirety of the blame for his perceived transphobia on an article from a gay publication from fifteen years ago, claiming that every criticism leveled against him stems from secondhand accounts of his work. Not, you know, the constant transphobia found in Sticks and Stones, or the current special he’s on stage performing.

There’s a certain benign quality in Chappelle’s regurgitation of old trans jokes, often too dated to truly offend, but The Closer takes a truly disgusting turn when he talks about a transgender friend of his who took her own life in 2019, days after the release of Sticks & Stones. Chappelle essentially blames the trans community for Daphne Dorman’s death, suggesting that she was bullied into suicide for defending him. The extended bit is a jaw-droppingly oblivious accusation to level against a community that faces grossly disproportionate levels of online abuse. His own jokes have supplied ample fodder for rampant online abuse of LGBTQ people.

A trust fund Chappelle started for Dorman’s daughter is flaunted as evidence of his allyship, using charity as a shield as he continues making transphobic jokes. He’s seemingly incapable of processing criticism through anything other than the prism of “us vs. them,” using that false binary to paint a portrait of people simply becoming trans to win the oppression Olympics, a tired trope completely detached from the realities of the trans experience.

Chappelle’s rampant transphobia doesn’t need to be a problem as long as the jokes land, but his obsession with grievances supersedes any pretense of crafting actual humor. He doesn’t look like he’s having any fun on stage, an audience that seems to pick up on this reality halfway through the special. He’s weirdly paranoid for a man being paid twenty million dollars for an hour of his time, afraid of a community with no foothold in the world he dominates.

There are fragments of a conciliatory message echoed in The Closer, often at odds with the rest of the special. Chappelle suggests he’d like a world where LGBTQ people felt included in his comedy rather than as the butt of the joke. That’s a hard proposition to consider when so much of his work these days isn’t really about comedy, but “cancel culture” and the perceived censorship by some of the world’s loudest voices. If Chappelle is sincere in his desire to make inroads with the trans community, he might want to start by crafting some more original material. Chappelle’s Netflix tenure started with a bang. With The Closer, the world’s greatest living comedian ends this chapter of his career with a resounding whimper.



September 2019



Sticks & Stones Isn’t Very Funny

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Five Netflix specials into his career resurgence, Dave Chappelle has a lot of problems with the way his jokes are being received in the #MeToo era. In the old days, comedians could punch down and tell tired jokes about the LGBTQ community, “alphabet people,” and nobody cared. Similarly, if you were a successful older man, there was a time when you could get away with making a younger woman watch you pleasure yourself.

Hearing Chappelle lament the dawning of the #MeToo era, you might get the impression that life is pretty hard for him. Sticks & Stones is largely centered around the reasons why he feels this way. Trouble is, the whole foundation of his routine is centered around faulty logic.

Chappelle is upset that people can’t make gay jokes anymore, seeming to forget that he can in fact, make those jokes. Sticks & Stones is full of humor directed at the LGBTQ community. He’s afraid of being “cancelled” while ignoring the fact that he’s currently being paid tens of millions of dollars to perform for one of the biggest outlets in show business. Paranoia aside, Dave Chappelle is far from canceled.

There is a fair amount of revisionist history about gay jokes present in Chappelle’s routine. He’s still upset about a time when Comedy Central objected to the use of a well-known anti-gay slur, wondering why he as a straight man wasn’t allowed to use it on television. Chappelle goes on to suggest that you can’t offend the “alphabet people” at all, putting aside the decades where it was considered taboo on television to portray an LGBTQ individual in a positive light. It’s kind of odd to see a comedian who’s been around as long as Chappelle try and act like gay jokes weren’t mainstream for a very long time.

Chappelle does seem to understand that there’s a reason why the transgender community isn’t collectively a huge fan of his. He’s also right that there is a fair degree in humor in the basic plight of the transgender identity. As a transgender woman, I laugh about the various ironies of transition all the time.

There are plenty of funny jokes to be told about the transgender community. Dave Chappelle just isn’t very good at that kind of humor. It’s not particularly original to compare transgender people to figures like Rachel Dolezal. The joke is certainly not all that funny in the year 2019.

Chappelle is hardly alone as a cisgender man in not really understanding the transgender identity. He takes that a step further in deciding that things he can’t understand must not be real, or the same as a person wanting to go around shouting racist Asian stereotypes. The theme of Sticks & Stones seems to be that Dave Chappelle doesn’t care about things that don’t directly affect him.

Lacking empathy can certainly be amusing, but Sticks & Stones is a tired routine by a man who forgot to layer jokes into his act, too often sounding like a pundit on Fox News. Chappelle used to be a master at making people laugh at inherently uncomfortable topics. He’s still willing to wade into controversial territory like pedophilia, but his bits just aren’t that funny. Chappelle allows the very notion that he shouldn’t be saying things to serve as the humor instead of actual jokes.

There are bits and pieces that prove Chappelle is still capable of understanding nuance. He uses a fairly amusing allegory about LGBTQ people riding in a car to describe the differences among the various groups within our community. Listening to him describe the ways that gay white men live have better opportunities transgender people sends a very different message than the special’s broader out of touch opinions of this changing world.

Dave Chappelle hasn’t lost anything because women now feel more comfortable speaking out against sexual harassment. Gay jokes aren’t as mainstream as they used to be, but Chappelle isn’t going to have his career ruined because he still thinks certain slurs are funny to say out loud. Dave Chappelle is doing fine.

The only potential hindrance to Dave Chappelle’s career is the fact that his edgy humor isn’t as funny as it used to be. The jokes in Sticks & Stones lack the complexity of his earlier work, sounding less contrarian than simply out of touch. Dave Chappelle shouldn’t worry about being “cancelled.” The far bigger threat to his career is the fact that he’s becoming quite a bore.