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Rewatching ‘The Chris Rock Show’ emphasizes the comic’s brilliance – and his continued problem with Black women

HBO Max is streaming the first two seasons of the show from the late ’90s

I was a preteen when The Chris Rock Show originally aired on HBO for five seasons from 1997 to 2000. I would sneak-watch any episode I could catch with the volume too low for my parents to hear the F-bombs or the skits I was too young to fully understand. But Rock’s ability to cut to the core of race in America, and bring out the most biting, funniest truth lured me into his brilliance and taught me so much about how to analyze and synthesize Blackness.

Other than a few DVD releases a few years after it aired, The Chris Rock Show has mostly lived on in short YouTube clips. So when HBO Max dropped the first two seasons of the show at the end of June, I was excited to revisit each segment, from Rock’s opening monologues to his man-on-the-street investigations and unfiltered celebrity interviews.

But I found myself pausing before hitting play and asking if I really wanted to revisit comedy I had loved decades ago when I was in middle school. Most of the things I deemed brilliant at 11 don’t quite hit the same anymore. Furthermore, we are in an era where debates over “cancel culture” and what is acceptable are being litigated daily, with comedy at the forefront of that tug-of-war.

From Kevin Hart declaring that “I’ve been canceled three or four times” to Dave Chappelle’s anti-transgender jokes for the sake of thumbing his nose at anyone offended to Katt Williams’ astute understanding of the benefits of adjusting, comedians are constantly in the news over how their art ages and the difference between growth and capitulation to the changes in audiences’ sensibilities.

Rock himself has taken aim at the entire debate, telling The Breakfast Club that cancel culture creates “boring” and “unfunny” comedians: “It’s weird when you’re a comedian because when you’re a comedian, when the audience doesn’t laugh, we get the message. You don’t really have to cancel us because we get the message. They’re not laughing.”

Watching The Chris Rock Show is a reminder of the blueprint that made Rock what he is now – brilliant, biting, preoccupied with the white gaze, incisive, classist, raw and antagonizing toward Black women. It’s all there in 17 30-minute episodes.

HBO Max took a calculated risk releasing the episodes and subjecting Rock, his writers and his guests to the scrutiny he and his peers seem so averse to confronting. I fully expected to see a show full of jokes indulging in anti-gay bias, anti-transgender bias, misogyny and more, along with a laundry list of reasons to chastise Rock and society for the way we treat the most vulnerable among us. And there’s plenty of that, for sure. But rewatching The Chris Rock Show in 2021 also provides a time capsule of what we were talking about, grappling with and willfully ignorant about at the turn of the century. A rewatch also provides yet another arena for us to figure out what to do with an artist’s past takes and how that impacts how we see that person years later.

There are plenty of aspects of the show that aged poorly and he and we have evolved beyond. But what fascinates me most is what has stuck with him through 2021, for better or for worse. The lack of growth being as telling as the places where his thinking has matured.

The show tackled the state of the world as it approached the 21st century and some of the biggest cultural stories of our lifetimes. Rock was like a tenacious defensive back, hawking every prominent news story like a wayward pass. He was there for the fallout of the O.J. Simpson trial, the beginnings of the Bill Clinton sex scandal, the Marv Albert scandal, the deaths of Biggie and Tupac, pre-9/11 ideals of patriotism, the start of Tiger Woods’ career and he even had a throwaway joke about the Pearl High School shooting, blissfully oblivious to the epidemic of school shootings on the horizon. Watching The Chris Rock Show is a reminder of the blueprint that made Rock what he is now – brilliant, biting, preoccupied with the white gaze, incisive, classist, raw and antagonizing toward Black women. It’s all there in 17 30-minute episodes.

The Chris Rock Show tackled the state of the world as it approached the 21st century and some of the biggest cultural stories of our lifetimes.

HBO Max

At the heart of Rock’s most famous and most divisive bits are jokes that reflect his preoccupation with the white gaze and, at times, what Black people need to do to gain white acceptance. His “N—as vs. Black People” bit from his 1998 stand-up special Roll With The New is about how “n—as” represent Black people who shirk responsibility, are lazy and commit crimes and how they’re different from the rest of Black people. “I love Black people, but I hate n—–s” is the refrain. The final punchline involves Rock relating that when he’s standing at the ATM he’s not scared of media narratives about Black people, he’s scared of “n—as.” It’s one of the most famous routines in all of comedy, and one of the most persistently troubling of Rock’s career. The same thinking that framed that joke runs all through The Chris Rock Show.

Take, for instance, his interview with civil rights leader Jesse Jackson in the second season. Rock asks Jackson why we are so focused on “the white man’s thinking” and why we can’t focus on “cleaning up the ghetto? … Of course, white people ain’t giving you a damn thing, why don’t you clean up your f—ing house?” Jackson brings up systemic racism and the fallacy of Rock’s point. They argue in a passive-aggressive, somewhat awkward few minutes.

It’s enthralling TV, for sure, but a reminder of where Rock stands and where his classist attitude leans into anti-Blackness. Another example is a skit where he asks people with GED diplomas what they do for a living and chastises them for not staying in school.

Respectability politics was a prominent feature of Black discourse in the late ’90s, with debates about “Black on Black crime” central to those conversations. So it’s easy to excuse Rock’s embrace of that ideology as a sign of the times. The problem, though, is that Rock has failed to evolve from that doctrine.

When he hosted the 2016 Oscars, for instance, in the midst of the #OscarsSoWhite controversy, he harped on the idea that the protests were only happening then instead of in the ’60s because “we had real things to protest at the time, you know? We had real things to protest; you know, we’re too busy being raped and lynched to care about who won best cinematographer.” Of course, in 2016, we were four years removed from the killing of Trayvon Martin and two years removed from Ferguson, Missouri.

This makes for a complicated legacy for Rock, especially because his show has so much poignant, precise commentary, especially when he goes off script and engages with guests, which are leaps and bounds the best parts of every episode. When he interviews Republican J.C. Watts, debating dog whistles (“They say welfare but they mean Black fare!” Rock yells) and school vouchers and reveals that Watts has no clue who musician George Clinton is, he creates legitimate laugh-out-loud moments on the strength of his timing and improvisational virtuosity. He spends much of his opening monologues lambasting the New York Police Department, highlighting now-forgotten brutality cases. And he roasts racism in Hollywood, making fun of Shaquille O’Neal’s Kazaam for turning the biggest NBA player around into a “slave” for a “white kid.”

Host Chris Rock speaks onstage during the 88th Annual Academy Awards at the Dolby Theatre on Feb. 28, 2016, in Hollywood, California.

Kevin Winter/Getty Images

The most hilariously timeless skit came in the pilot episode when Rock tried to rename a street on Howard Beach in New York to Tupac Shakur Boulevard. It’s the kind of stuff that makes Rock undeniable – revealing a racist pathology in America while making you laugh the whole time.

Rock is also great when he’s just hanging out with other funny people, talking shop in a way that’s rare for the formulaic late-night show interview. Like when he’s hanging out with George Carlin or talking to Chris Spencer about the controversy over the Vibe late-night show competing with the Keenen Ivory Wayans Show. (Remember that?) Rock seems genuinely at ease trading stories with Arsenio Hall in an interview that featured a break in the middle for a Bad Boy Remix of the interview that had me laughing louder than the audience.

Alas, his interviews with Black women are as uncomfortable to watch as they are informative about another issue Rock has had throughout his career: his antagonistic and belittling relationship with Black women. When Jada Pinkett Smith is on the show, their conversation revolves around the Million Woman March, an event Rock never quite seemed to understand, and is a butt of his jokes throughout the second season: “What was the Million Woman March about? Because Black women are all right!” Pinkett has to explain that, surprise, Black women experience oppression as well.

It’s illuminating and refreshing, then, when Jenifer Lewis is a guest in the second episode, revolving around Valentine’s Day. Lewis comes out with furry handcuffs, talks about a man she plans on sleeping with when she gets home and absolutely overwhelms Rock. He has no clue what to do with her when she’s gone on the offensive and he can’t talk down to her or quell her forthrightness.

Sure, we can look back at the way society regarded gender and the rampant misogyny of the times, but Rock’s relationship with Black women hasn’t changed much in the years since. In season two, Rock complains to Vivica A. Fox that she plays a stripper in Independence Day. His disdain for sex workers runs all through the show, including a skit that argues that strippers can’t claim sexual harassment.

The formula is still in Rock’s DNA. Much of his latest special, 2018’s Tamborine, was about his divorce, earning backlash for his portrayal of Black women in relationships. And, of course, there’s his 2009 documentary Good Hair that paternalistically ridiculed Black women for wearing weaves and wigs, an approach panned by many Black women.

The show is also home to numerous anti-gay and anti-transgender jokes across the first two seasons. Throughout the episodes, I watched jokes about Michael Jackson being gay or a skit that ends with a character played by Rock revealing to Lil Kim he’s transgender after they’ve been dating as a “gotcha” punchline.

Anyone who doesn’t want to engage with the old episodes or Rock himself after these jokes is well within their rights. I’ve always felt that there’s no such thing as an overreaction to aspects of our culture that harm the most vulnerable among us. One person’s belief about being “overly sensitive” is another’s righteous outrage over something that has pained far too many for far too long. 

Yes, Rock has moved beyond a lot of that content, and thankfully so. But it was as wrong in the late ’90s as it is now, regardless of who was laughing along with it or what was deemed socially acceptable. Rock, and others like him, are better off trying to reckon with that past and accept the criticism that comes their way.

Ironically, there’s a moment in the second season when Rock is interviewing broadcaster Bryant Gumbel and he begins with an apology about a joke he had made a decade earlier: “If someone told Bryant Gumbel he was Black, he’d have a heart attack.” Rock goes on to say, “It came from my ignorance of ‘this is where I grew up’ and everything. Like, any Black guy that spoke well was considered white. And I’m glad that people are, like, growing the f— up.” The two go on to have a pleasant conversation about Blackness and identity.

For many of us, that’s all it takes. Acknowledge the wrong, recognize where it came from and try to do better. It’s amazing that Rock understood this in 1998 and yet he and so many of his peers can’t grasp the concept in 2021.

Overall, The Chris Rock Show is an exploration of the mind of a superstar comedian and one of our foremost cultural commentators. In these episodes, we see what made him so revered, so maligned and so complicated. While comedians want to move on from the jokes they no longer make, the most revelatory information here is what persists because the artist doesn’t feel evolution is necessary. That’s where we learn what’s at the center of our most talked-about public figures.

David Dennis, Jr. is a senior writer at The Undefeated and an American Mosaic Journalism Prize recipient. His book, The Movement Made Us, will be released in 2022. David is a graduate of Davidson College.