The Boondocks’ relationship with Blackness has always been complicated.

Characters of The Boondocks animated sitcom
HBO Max/Warner Media
Hits Different
ByDylan Green

What “The Boondocks” didn't understand about Blackness in the 2000s

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A “Nigga Moment,” as described by character Huey Freeman during the first season of the Adult Swim series The Boondocks, is when “ignorance overwhelms the mind of an otherwise logical Negro male, causing him to act, well, like a nigga.” At face value, it was a simple and funny premise when first introduced in the 2005 episode “Granddad’s Fight,” as barbed commentary wrapped in wry observational humor.

Rewatching this episode nearly 15 years later, I became stuck on what Boondocks creator and head writer Aaron McGruder’s idea of a “nigga” is. Is the joke punching up at white (and non-Black) perceptions of Black Americans through satire? Or punching down at the perceived toxicity of “ignorant” Black people with backhanded humor? I found my answer when watching the third episode of the show’s third season, “Stinkmeaner 3: The Hateocracy,” which builds on the Nigga Moment lore by including some extra caveats. The episode introduces the idea of “nigga synthesis,” where Black people create bonds with each other over shared ignorance. The only thing that can end a Nigga Moment for good? Jail. A brief monologue from character George Pissedofferson near the episode’s end sums up the show’s, and McGruder’s, stance on what exactly a “nigga” is: “We don’t need a reason to fuck shit up. That’s why we drink Hennessy, that’s why we smoke menthols. ‘Cause we niggas. We likes to ruin shit.”

The revelation was funny in the moment because it’s coming from a character who’s a stand-in for archetypes of a previous generation of Black comedy. That kind of satirical lens being focused on Black entertainment felt edgy and fresh in 2010. But today it leaves a sour taste for a few reasons. Like most of the show’s jokes, it wraps a cultural dog whistle in a familiar sitcom plot. It’s a broad swipe at what people consider to be “ignorant” behavior, implying that simple pastimes like drinking cognac or smoking a specific brand of cigarette can somehow corrupt someone on a moral level. What started as a fairly edgy joke in its infancy evolved into an antiquated idea that doesn’t pass the smell test over a decade later. While a lot of the show is still genuinely funny and thought-provoking, The Boondocks has plenty of misfires. Its attempts at smuggling snarky commentary on Black culture that boomerang on themselves relies on the same stereotype-riddled images used to oppress Black people for centuries.

The Boondocks, based on the comic strip of the same name first published in 1996, follows the Freeman family as they move to the fictional suburbs of Woodcrest after years of living in Chicago: 10-year-old Black radical Huey, 8-year-old faux-gangsta Riley, and Granddad. The show is a fish-out-of-water concept that comments on contemporary Black culture in the 2000s, BET, the fallout of Hurricane Katrina, colorism, and the legacy of the 2004 film Soul Plane.

BET, which was founded in 1980, had come under fire for portraying negative stereotypes of Black people in the late ‘90s and early 2000s. This made the station and spiritually similar content like Soul Plane the perfect scapegoat for anyone looking to place the blame somewhere. McGruder was no exception, as both The Boondocks comic and TV show took several swipes at the network. It became a recurring theme throughout the series’ initial lifespan, even resulting in two season 2 episodes — “The Hunger Strike” and “The Uncle Ruckus Reality Show” — getting banned from the airwaves in fear of lawsuits.

The Boondocks skewers BET with edge and thoughtfulness in “The Hunger Strike,” which depicts the heads of BET corporate offices as conniving buffoons — particularly then-CEO Debra Lee, who’s retrofitted into a parody of Dr. Evil from Austin Powers. It’s arguably more ridiculous than King coming back to life, but it puts the onus of BET’s issues exactly where it belongs: With the corporate (and white-owned) overlords who really pull the strings.

Some of the characters are timeless icons of satire. There’s self-hating Uncle Ruckus, a Black man with a glass eye who insults Black people and reveres whiteness with hilarious intensity. And then there’s Ed Wuncler III and Gin Rummy, two white men so enamored with Black culture that they’re voiced by Charlie Murphy and Samuel L. Jackson. There are moments in the show that critique the culture around snitching, and McGruder imagined a historical action movie based around a freed slave years before Django Unchained. The show the notion of what Black television could look and sound like in the 21st century. But for every prescient character like the Django-adjacent Catcher Freeman, or the rapper and neighbor Thugnificent, there are a handful of messages that no longer translate — and, honestly, didn’t fully translate back then.

Consider “Return of the King,” the ninth episode of the show’s first season. The episode creates an alternate reality where Dr. Martin Luther King Jr. falls into a 32-year coma after being shot in 1968 instead of dying. He awakens in the year 2000, becomes a pop culture icon, and signs a deal to publish his autobiography. But after an appearance on a talk show where he suggests that Americans “turn the other cheek” in response to the terrorist attacks of September 11, King becomes a social pariah and briefly moves in with the Freeman family.

King and Huey share two pivotal moments in this episode. Having missed out on 32 years of cultural evolution, King watches BET and becomes depressed by the state of Black America. “What happened, Huey? What happened to our people?” he asks, exasperated. “Everyone was waiting for Martin Luther King to come back,” Huey says. Later, after the pair organize a meeting for King’s new political party, they can’t get into the event because, unknown to King, he hired a street promotion team that turned the planning meeting into a club event. As King looks out into the crowd, who are dancing and fighting and joking away, he finally snaps: “Will you ignorant niggas please shut the hell up?” He goes off on a tirade, chastising Black Americans for not living up to the standards he and other Civil Rights leaders fought for decades ago. Afterward, he thanks Huey for his help and declares he’s moving to Canada. Ouch.

The episode was ridiculed at the time (including by the Reverend Al Sharpton) for featuring an incarnation of Martin Luther King Jr. using the n-word. But the speech at the episode’s climax is problematic for many other reasons. It features King, a figure who understood the power of media and how it affected the masses, using respectability politics to bully a generation into protesting for equal rights. And it wasn’t a speech used for satirical purposes, dressed down to address why that thinking might be myopic or dangerous. Huey’s last line of dialogue in the episode is “It’s fun to dream,” revealing the whole thing to be imaginary. It also implies that this is a stance Huey, and by extension McGruder, endorses, something they wish could happen.

The idea of using one of the most important civil rights figures of all time to sound off about how you think BET and rap music is ruining the youth is shallow and offensive — it’s shock for shock’s sake.

“Return of the King” and the Nigga Moments saga aren’t the only instances of Boondocks satire that crumble under close inspection. Like most comedy in the early 2000s, the show is also rife with homophobia. This is unfortunate because the episodes involving Gangstalicious, a rapper who’s secretly gay, attempt to comment on how toxic masculinity manifests in a world where Frank Ocean had yet to come out publicly. In the third season episode “Pause,” Granddad joins a cult led by a character named Winston Jerome — a brutal takedown of Tyler Perry and his infamous Madea character. It does good work aping Perry’s aesthetic, but takes things too far when the episode’s other recurring joke involving Granddad learning the phrase “no homo” is used to berate Jerome. There’s an interesting idea about using religion to deny your own sexuality that’s hiding in the episode, but it never develops beyond point-and-laugh moments of Jerome cross-dressing and singing parodies of songs from The Rocky Horror Picture Show.

One aspect of the original comic that could’ve helped ground the show is the character of Caesar. In the comic, Caesar is Huey’s best friend who usually echoes his political and social worldview but also serves as a more positive foil to Huey’s sullen outlook on life. Their dynamic was a gravitational pull that kept the central idea of Huey’s character — a 10-year-old Black radical leftist in the vein of Huey P. Newton — from flying off into the atmosphere. After all, most of the main and supporting characters on The Boondocks, particularly the Freemans themselves, embody some sort of archetype. On the show, Huey is the binding agent and since he’s already an overblown archetype, he’s asked to hold the narrative down in a way he’s not always designed to. Caesar’s character was more neutral and brought a balance to the story that’s ultimately missing from the show.

It may feel unfair to judge The Boondocks, a show that premiered nearly 20 years ago, with modern eyes and sensibilities, but as its legacy grows on the heels of its upcoming HBO Max reboot, popping the hood on the series is healthy. The fact that McGruder was able to get an uncompromising Black show as this on TV at all is commendable, and many of its best episodes still hold up today. But even the most fearless satirists have blind spots; the edgiest of us can sometimes slip and tumble while staring into the abyss. The Boondocks’ relationship with Blackness has always been complicated, but it’s worth considering how it sometimes used its humor to point accusatory fingers in the wrong direction.