In Short: F*ck Yo Couch

In the same way that classic rock fans will debate the greatest guitarists in history (it’s Jimi Hendrix), or hip hop fans will debate the greatest rapper alive (it’s Jay-Z), comedy connoisseurs love to debate who’s the GOAT – the Greatest Of All Time – in comedy.

Secular atheists will tell you George Carlin. Faux-intellectuals will tell you Charlie Chaplin and his physical brand of humor. Fans of classic comedy will tell you either Richard Pryor or Eddie Murphy. Your edgy uncle will tell you Bill Burr, because he, and I quote, “Tells it like it is.”

But really, the answer to this query is quite simple. Who is the only comedian to have a career spanning four decades, among movies, television, stand-up, award shows, and whatever the hell 8:46 was earlier this year?

If you guessed Dave Chappelle, congratulations, you’re correct.

Yes, from his cult classic films in the late 1990s – as poorly as they may have aged – to the smash sensation that was Chappelle’s Show in the 2000s to the past few years of biting stand-up specials filmed for Netflix, Dave Chappelle is the undisputed GOAT of comedy.

Let’s break down why.

Longtime fans of the man himself will call back to his comedic career beginnings in the 1990s. Between stoner comedy films like Half Baked and his classic presence as a legendary stand-up staple in shows on both coasts.

Perhaps the highest success of this early era, the HBO-aired Killin’ Them Softly, showed a national audience early on why this man was a legend in the making. He excoriated gender roles, lampooned drug use in black culture, and even noted how his race was moving up on the social totem pole due to white Americans being so afraid of Arabs.

Chappelle followed up this masterpiece four years later with For What It’s Worth, solidifying himself in the stand-up lane as an icon. However, he had higher aspirations than just doing stand-ups, and those aspirations helped inform his cultural status today.

The obvious culprit is Chappelle’s Show, which ran on Comedy Central from 2003 to 2006. By the time of its second season, the show, co-created by Dave and comedic partner Neal Brennan, was the highest-rated show on the network.

It introduced the world to comedic rising stars such as Bill Burr and Joe Rogan, as well as revitalized the career of past legends such as Arsenio Hall and Charlie Murphy. Musical game-changers like Jamie Foxx, Kanye West, and Mos Def all played roles on the show, as did jazz rap visionaries like Q-Tip and the Roots.

Chappelle’s Show was at once a once-in-a-lifetime cultural phenomenon, a forum where the best of humor and music intersected, and a raucously cutting sketch comedy series. In just under thirty episodes, the series single-handedly crippled the sketch comedy sphere, as every poor imitation (Key & Peele, Inside Amy Schumer, etc.) fell so far short of the original.

Antagonistic comedy sketches dealing with gender, sexuality, fame, and especially race formed the backbone of Chappelle’s Show, leading to mass popularity and critical acclaim. Today it’s widely considered as one of the best TV shows of the twenty-first century, and one of the best comedy shows of all time.

Comedy Central understood the ratings cash cow that the show was, leading them to infamously offer Dave $50 million for a third and fourth season, which he declined. Citing creative exhaustion and comedic fatigue, as well as disillusionment with the show’s process and success, Dave fled to South Africa, quitting the show and leaving television for more or less forever.

The next decade was pretty quiet for Chappelle, who would pop up once or twice in a surprise venue for a show – or as part of a Kendrick Lamar routine at the Grammy’s. When he did eventually return, however, he came to burn down the house.

In the back half of the 2010s, Netflix announced that it had signed an exclusive streaming deal for new Dave Chappelle stand-up specials, at twenty million dollars per special. Yes, that’s right. Twenty million – per special.

Unsurprisingly under terms like those, Chappelle has been a busy, busy man these past few years, releasing five specials since 2017. However, if you’d think that his quality level would go down because he’s going from being a ghost to being one of the most prolific comedians of the late 2010s, you’d be mistaken.

Dave Chappelle is on fire. In fact, he’s arguably more on fire now than ever before.

Don’t get me wrong, I adore watching Chappelle’s Show reruns and putting in my DVD of Killin’ Them Softly (when I can find a DVD player). But if young Dave was a misanthropic, absurd satirist, ready to set fire to the world that has consistently screwed over his loved ones, older Dave is something else altogether.

In 2019’s Sticks & Stones, arguably his most notorious stand-up special in years, Dave spends nearly an hour lampooning cancel culture. He roasts Jussie Smollett, he compares the LGBT+ movement to a car where three out of the four people feel like they’d get a lot farther without the final person, and he tears into Michael Jackson, R. Kelly…and their accusers.

In Los Angeles, he chides the #MeToo activists (with whom he agrees) for taking things so far that the blowback has fallen on women everywhere, while in Texas he discusses the parallels he sees between the current opioid epidemic and the crack crisis of the 1980s – and as he says, he understands now why white people didn’t care back then.

This modern era of Dave Chappelle is lean, mean, and cynical. He’ll just as easily do a twenty-minute monologue with no jokes about police brutality, like he did earlier this year following the George Floyd killing, as he will make jokes about Lil Wayne lyrics he can’t relate to.

He’s an older, bitterer man, but still a comedian who we can all rally around for saying the things we never dare. He’s still the best storyteller in comedy, and this current era has proven once and for all that Dave Chappelle is the GOAT of comedy.