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The Two Daves

Dave Chappelle is more conflicted than ever

Critics and comedy fans laud Dave Chappelle for his analysis of American race and social relations, yet his finest skill might be the way he manipulates time on the stand-up stage. You see it first in obvious ways—as, for example, in the contrast between his deliberate joke set up and his spontaneity. When Chappelle is shifting gears in this mode, he ad-libs zingers during downtime in a longer monologue and improvises crowd burns. (He asks a black guy who shouts out “Santa Monica,” if he’s wearing Vans sneakers, the ultimate suburban fashion statement.) The other trademark Chappelle intervention is more subtle; he can start a joke in a way that suggests his political take is progressive, only to deliver a punchline that undoes his audience’s high-minded expectations. 

This is a common deflationary tactic in his first new stand-up specials in more than a dozen years, Netflix’s The Age of Spin (2016) and Deep in the Heart of Texas (2015). In both, Chappelle plays with the idea of progress. For example, in Spin, he offers advice to the LGBT community:

I understand why gay people are mad, and I empathize. I’m just telling you this as a black dude. I support your movement, but if you want to take some advice from a Negro, pace yourself . . . these things take awhile. Just cause they passed the law doesn’t mean they’re gonna like you. Brown v. the Board of Education was in 1955 [sic]; somebody called me a ‘nigger’ in traffic last Wednesday. It takes a minute.

Soon after, he jokes about the meaning of the letters in the LGBTQ acronym: “Of all those letters, the ‘T’ has the toughest road ahead. In fact I think the ‘T’ should stand for ‘Tough Road Ahead.’” This could come off at first as an empathetic view of the difficulties transgender people face in society. But, wait for it . . .  “They’ve got the longest mental gap to bridge, that’s all I’m saying. Cause, you know, whenever I see one of them ‘T’s’ on the street I don’t mind them, but I be like: ‘Man, I miss Bruce.’” Seconds later, he offers a fairly liberal take on Caitlyn Jenner’s transition, when he kids about seeing Kanye West saddened by the realization that he now has two mothers-in-law. Right after that, he makes a dumb joke about a trans businesswoman throwing a penis in a boardroom. Then he suggests that trans women trick men into having sex with them. This cluster of jokes sums his conflicted sensibilities as a performer: smart social comedy and dick jokes. 

A couple of unexpected cackles can unnerve and confuse anyone pondering the state of our country in the same way that exit-polls can.

Chappelle’s sharp comedic timing is on fresh display in these sets, where he builds bridges over his own mental divides, only to demolish them seconds later. His material, which also includes meditations on his home life, fame, Bill Cosby, sex-tape extortion, disgraced former LA Clippers owner Donald Sterling, police brutality, and other hot-button topics mimics Chappelle’s stuttered approach to comic timing. The jokes are simultaneously topical and a little stale. These specials are a bit like sputtering time machines moving across the country’s zeitgeist—and in the process, indicting the progress of our comedic narrator and the oft-deranged nation he describes. The jagged movement here recalls a 2004 Chappelle’s Show sketch called “The Three Daves,” a triptych of vignettes that chart the comic’s emotional growth (or lack thereof) at ages eighteen, twenty-four, and thirty. In these Netflix sets, he’s Dave at forty-one and forty-two, and he can make thirteen years seem like no time at all. Sometimes you marvel at how ahead of his time he is, and at others you realize how a dozen years out of the spotlight can diminish a comic’s persona.

So much has happened since Chappelle’s last special, For What It’s Worth, premiered in 2004, and Chappelle’s Show both skewered and dominated American pop culture in the early aughts. In 2005, Chappelle famously walked away from a $50 million deal with Comedy Central to extend the run of Chappelle’s Show, citing his own mounting discomfort with the effect his comedy had on black America and his own self-esteem. In the interim, his appearances were limited: he would have one-off moments in the spotlight, on Oprah, Dave Letterman’s Late Show and Sundance’s Iconoclasts with the late Maya Angelou, together with a few episodes of Inside the Actor’s Studio. Chappelle’s long sabbatical only added to his legend, with his fan base alternately wondering whether he was a reclusive genius or simply crazy. (Which side of the debate you came down on usually had to do with your race.)

Then, all of a sudden after years of playing festivals and trying out materials in clubs, he returned to the mass media with one of the most daunting gigs imaginable: hosting Saturday Night Live the weekend after the 2016 election—and for the first time, no less. The political landscape isn’t the only thing that’s changed since his departure. Chappelle, who was once rail-thin, now has a buff physique that strains against his clothing. His voice, too, is decidedly bulked up—his smoking habit has added gravel to his accent. 

After more than ten years out of the spotlight, the two hour-long specials seem to have abruptly streamed their way on to Netflix to make up for lost time. At the same time, though, they have the effect of bisecting Chappelle’s material, between the personal and the pop-political. Since they represent disparate halves of Chappelle’s outlook, they’re best enjoyed together. The Austin-set show Deep in the Heart of Texas (2015) is more personal and laid-back, while Spin gleefully goes for the jugular in matters of race, sex, and celebrity culture. The latter is a tightly crafted, Hollywood-focused hour that’s organized around the four times he met O.J. Simpson. The show is so heavily about the surreal nature of showbiz life that it could be exposure therapy. 

Chappelle’s new Netflix star turn is subtly focused on how evolution occurs within a conflicted mind.

In Texas, he mostly moseys through material, chain-smoking and riffing loosely. Along with the transgender jokes, there are stupid ones about rape that counteract his brilliance. Though, when he’s setting up a joke about Ray Rice, a few audience members cheer when they learn Rice will play football again. Plenty of people laugh at Chappelle pitching a movie about a raping superhero. And that’s what I mean about progress and its halting nature: as with the results of the presidential election, a couple of unexpected cackles can unnerve and confuse anyone pondering the state of our country in much the same way that exit-polls can. He’s perfect when he’s both profane and profound, as with an observation that the sheer number of accusers makes Bill Cosby the “the Steph Curry of rape.” It’s a crass statement, and it’s easy to think that Chappelle’s just scoring an easy laugh via the glib comparison of sexual assault by to an NBA star’s statistical genius. But by pairing the Cosby allegations with Curry, a wholesome black hero of our time, he points to the outsized innocence that defined Cosby at one time, too.

Despite the looming presence of Cosby and contemporary black comics like Kevin Hart, it’s Dick Gregory’s spirit that runs through these two hours. In the sixties, Gregory made a series of albums that highlighted comedic double consciousness. East & West (1962), was composed of two sets pitched at different coastal audiences in San Francisco and New York. The Two Sides of Dick Gregory (1963) showcased Gregory’s own divided brand of early sixties showbiz activism, while The Light Side: The Dark Side (1969) did similar work later in the decade. Chappelle’s Netflix double feature is like Gregory’s sixties output in that it’s politically engaged and irreverent. And like those Gregory albums, Chappelle’s new Netflix star turn is also subtly focused on how evolution occurs within a conflicted mind, and what the passing of time can do to change or cement certain impulses. When his third Netflix special premieres later this year, it’ll be fascinating to see how he handles the Trump era—though with Chappelle, it almost doesn’t matter how current the events he’s mined for his material may be.

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