If money is indeed the key to happiness, Dave Chappelle has certainly experienced a range of emotions since he famously turned down $50 million USD to continue doing his critically acclaimed series, Chappelle’s Show – which resulted in an abridged third season –  and his fading into the background as a newer breed of comedians/sketch artists like Kevin Hart, Amy Schumer and Key & Peele began carrying the torch.

At the time of his departure from the limelight, people lost their collective minds at the prospect of someone leaving that amount of money on the table.

Whenever he gave a rare interview, all the headlines beckoned, “Chappelle Comes Clean” as if he had to drop some type of truth bomb on why money alone couldn’t sway him to keep making us laugh.

Despite his continued absence between 2006-2010, the enthusiasm for a return from his fans never wained – even after news broke that Chappelle’s inevitable return to the stage in 2011 resulted in the comedian “sighing”his way through a 45-minute set – where he was showered in boos and cries that he had officially lost his mojo, mind and millions of dollars.

Personally, I viewed this period for Chappelle as similar to when Michael Jordan decided to play baseball. Nothing about basketball excited Jordan anymore; not the championships, not the praise and certainly not the money.

We understood it. But nothing about watching the greatest basketball player of all time become a mediocre baseball player felt right.

Similarly, watching Chappelle struggle to find his voice when we knew what he had with Neal Brennan on Chappelle’s Show was equally discouraging.

13 years after his last comedy special – 2004’s For What It’s Worth – Chappelle is back in an official, stand-up capacity on Netflix which carries the weight of a $60 million price tag spread out over three specials.

When Jimmy Kimmel asked him what prompted him to release two specials at a time, Chappelle cracked, “money,” much to the delight of both Kimmel and the audience who seemed to understand that the joke could play into any number of factors relating to his absence from the media.

Personally, I’d like to believe that the money never mattered to Chappelle.

Rather it was the only absence of comedy, crowd and critique from his life which brought about his two specials.

I have to admit, there was a little bit of trepidation when pressing play. I didn’t want to see .225-batting Michael Jordan leg out an infield single. I wanted the tongue-wagging, gravity defying Air Jordan who seemed to float.

Thankfully, that’s exactly the Chappelle we got.

The Age of Spin: Live at the Hollywood Palladium

As crazy as it seems, Dave Chappelle tells the audience at the packed house at the Hollywood Palladium that it has been 10 years since he played a show in Los Angeles – which in relationship terms – means that his breakup with standup comedy was so severe he couldn’t even come back to a major metropolitan city that he and his muse had once inhabited together.

It’s with that spirit of failure that Chappelle begins his show, talking about the pitfalls of comedy itself, and his long road back to prominence which included a fateful stop in Detroit.

“Dave Chappelle Drunk on Stage in Detroit, Booed off Stage” he cracks, mimicking TMZ’s headline of a show from 2015 where he was working out the rust – and fans weren’t open to him using the stage more how surgeons of yesteryear experimented on patients in hopes of advancing the discipline – instead of the laser-like precision of procedures today.

As he lets the hurt of that encounter sink in, the punchline hits with ferocity.

“I was booed…I did not leave.”

From even that earliest moment in the show, Chappelle had the crowd. His thesis statement in a nutshell: it’s not always going to be easy or comfortable when I have this microphone, but you’re going to leave knowing what’s on my mind.

Chappelle may have his insecurities and trepidations as it relates to how his special will be received, but you would never know it in this moment.

“Because not only did I bomb,” he continued. “I had to go back to the very same room the next night and do it all over again. That would be like if you were having sex with a woman and — for some reason, this would never happen, but for some reason — she had a mousetrap in her pussy. And you get caught in the trap. And then you got to fuck her again tomorrow night. I’d still do it, but I’d be careful the next time.”

He even suggests that in this turbulent world that we live in – where race and political leanings continue to divide us – his comedy shows and their faults can actually unite people from all walks of life.

One of Chappelle’s greatest strengths is that he is equal parts storyteller as he is an accomplished comedian. In turn, viewers can’t help but sit on the edge of their seat in anticipation for a punchline that maybe be the next word, sentence, or even five minutes from when he started.

There is no greater evidence of this attribute than when he begins an impassioned observation about how greatly the world has changed since World War II ended. The crowd murmurs – not out of frustration or angst – but because Chappelle’s assessment of the plight of African-American men who fought in the War and all the women who entered the workforce and picked up the slack was so spot on.

And then the punchline comes out of nowhere and hits with impact as it relates to the allegations of Bill Cosby’s alleged sexual assault of over 60 women during this same period.

The way Chappelle handles Bill Cosby isn’t necessarily how you would expect. That isn’t to say that Chappelle ever even attempts to condone what he has been accused of, but rather the feeling that people might have had upon learning that the man who reportedly – albeit unconfirmed – bought the PA system for Martin Luther King Jr. to deliver to “I Have a Dream” speech and who’s sitcom drew Super Bowl-esque viewership numbers, was actually a monster.

“I’m a 42-year-old black comedian. Obviously, Bill Cosby was a hero to me,” he says. “I didn’t wanna believe the allegations. It would be like if you heard chocolate ice cream, itself, raped 54 people.”

It’s with this same lens that Chappelle also gets to the issue of OJ Simpson – with whom he recounts four different instances of running into the infamous Hall of Fame running back at various stages of his own comedy career.

“Man the fuck up or you’re not gonna make it to the end of the show,” he says after a bold assertion about Simpson’s ex-wife, Nicole Brown Simpson.

Chappelle goes on to describe one particular encounter, saying, ““I’m just telling you what I saw, with my own eyes, you can believe me, or not believe me, but, in my experience, O.J. Simpson … one of the nicest men I have ever met. He was nice to me. He was nice to my friends. The conversation was filled with warmth and levity and humor and wisdom. We talked for 90 minutes and then suddenly the Juice said, ‘You know what? I got to be going, but it’s good to see you again and I’m glad things went so well.’ I said, ‘Thanks, Juice.’ And my friend said, ‘Good-bye, Mr. Juice.’ They’re new to the game. He said, ‘No, thank you for your hospitality. Good night, guys.’ And we said, ‘Good night.’ And he just walked out of the room. And as soon as the door closed, we all looked at each other like, That nigga did that shit.”

If there were one main element to gleam from this first hour, it’s that Dave Chappelle is fearless. He could have delivered a safe set and people would have eaten it up because when it comes to greats of their disciplines like Dave Chappelle, we take what we can get.

Deep in the Heart of Texas: Live at Austin City Limits

Although it is technically the second special in Chappelle’s arsenal, Deep in the Heart of Texas: Live at Austin City Limits was filmed in April 2015 – a good year before the aforementioned set in Los Angeles. Thus, you can see the comedian still working out some of the kinks – yet blindly unafraid to touch on various sociopolitical topics like racism in America.

Much in the same way that his special in Los Angeles deals with being heckled in Detroit, Chappelle starts his set in Austin by recalling a similar incident in Sante Fe, NM where someone threw a banana peel at him while on stage.

Like with many autobiographical elements in Chappelle’s life, this experience transitions to an equally disturbing encounter he had in the city where he resides – Yellow Springs, OH – when a car full of white teenagers hurled a snowball and a racial epithet at him and his sister.

After the police get involved, Chappelle muses, “I’ve never been in the position to determine the fate of white children before.”

You can tell the audience is waiting for the punchline, but Chappelle either isn’t angling to tell a joke, or he’s milking this sprawling tale for all it’s worth and it’s merely an indication that his life as a black man in America – even as a famous person – is horrifying.

He continues to tug on people’s heartstrings as he recalls meeting with one of the teenager’s mothers who doesn’t want her son’s life marred by this one incident. And then Chappelle gets a little twinkle in his eye.

“Maybe you could just suck my dick a little bit,” he cracks, microphone bouncing off his knee as he can’t help but laugh at his own joke.

Chappelle is even self-referential as it relates to the material he is delivering. One particular bit about “pussy juice” finds him darting around, testing the waters for what gets the biggest laugh and even admitting he has fifty different jokes stored up on that topic alone.

His mannerisms and attitude even suggest this is an informal affair; opting to pull up a stool, place his feet on the speakers and call for a cigarette from someone in the crowd.

Overall, it feels like a lecture on what Chappelle finds funny more than anything else, and that’s definitely not a bad thing.

As a complete body of work, the Netflix specials reveal an older, wiser and perhaps more cynical Dave Chappelle who is not immune to flurries of inappropriateness. He is after all, a comedian and not a politician.

If there is a main criticism to be had, it’s that some of the subject matter feels particularly dated as it relates to scandals involving Ray Rice, Paula Deen and Donald Sterling.

On a personal level, I was left with two things that indicate Dave Chappelle’s brilliance. He states of young people today, “How can you care about anything when you know about everything?” as it relates to our over connectedness.

This isn’t Dave Chappelle setting up a joke, this is him telling it like it is.

Secondly, he is masterful at packing criticism on race, gender and LGBTQ issues in just a short sentence, saying, “I know black dudes in Brooklyn, hard, street motherfuckers, who wear high heels just to feel safe” – referencing how the only refuge from police violence for a black man is becoming a black woman.

As he wobbles around on stage pretending to shuffle in high-heels, it’s a reminder that jokes shouldn’t be taken so literally and Dave Chappelle ultimately doesn’t care if he offends you.

Whether he’s donning “45” or “23,” Dave Chappelle is definitely back.

Words by Alec Banks
Features Editor

Alec Banks is a Los Angeles-based long-form writer with over a decade of experience covering fashion, music, sports, and culture.

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