The Best Episodes of 'The Boondocks'

A look back at 'The Boondocks,' one of the most important television shows on the black experience in America.

Riley, 'The Boondocks'

Image via adult swim

Riley, 'The Boondocks'

Aaron McGruder's The Boondocks deserves to sit in the pantheon of Black entertainment. Not many series—animated or live-action—nailed its subject as perfect as The Boondocks did, and as the years go by, we continue to see how impactful (and important) this series was.

As many know, The Boondocks started out in 1996 as a comic strip written and drawn by McGruder (and a small team of like-minded individuals). The show spent the next ten years gaining popularity, newspaper syndication, and causing controversy for McGruder's satirical voice, all filtered through three characters: Granddad, an older black man who saw the civil rights movement and is just trying to live in the suburbs with his two grandsons, Riley (the hip-hop-obsessed wannabe thug) and Huey (essentially, Boots Riley from The Coup)—although it further expanded its universe to include "Uncle Tom" (who was actually named Tom), a black guy who hates black people, a biracial girl who was confused af, and so many believable portrayals of the everyday black people we meet. Never afraid to skewer everything from social issues to the state of hip-hop, when word got out that McGruder selling the rights to The Boondocks for an animated show on adult swim, it was wildly known that it was going to be "that show." We'd lost Chappelle's Show in 2005, and were missing the informed voice on all of the fuckery facing black lives in America.

See, The Boondocks as a cartoon could do what shows like In Living Color couldn't: it was able to say things about current events and long-known struggles and situations in black America that some shows couldn't (although Dave Chappelle definitely got the closest). It covered issues like soul food, the war in Iraq, homophobia, "nigga moments," slavery, and so much more in ways that were as witty as they were real, in an anime style that allowed for some truly memorable sequences.

While it's a goddamn shame that a) McGruder left after three seasons of the show and b) the fourth season left a meh taste in the mouths of many, The Boondocks goes down in history as one of the realest shows about the black experience in America, even if its just a bunch anime(-influenced) characters spitting foul language and getting into fuckery. Complex's Boondocks consortium put their collective heads together and paired down the show's history into the 15 best episodes of The Boondocks, which you can stream on HBO Max (well all of the episodes except for "The Story of Jimmy Rebel", which was recently removed from the service).

15. Return of the King (Season 1, Episode 9)

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Air date: January 15, 2006

Have you ever wondered what would happen if Dr. Martin Luther King, Jr. had survived the assasination attempt on his life? It'd probably be a lot like this episode of The Boondocks, to be honest. Imagine the media frenzy and misplaced joy that many of today's confused leaders—and most importantly, the youth.

If you want to just skip to the trillest shit ever on an episode of The Boondocks, just peep that King speech up above.—khal

14. A Huey Freeman Christmas (Season 1, Episode 7)

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Air date: December 28, 2005

You have to applaud Aaron McGruder for birthing a proper spin on A Charlie Brown Christmas with this tale of making Santa pay what he owes, mashed up with the confusing state of "WTF are we even celebrating during the holiday season" with a white teacher's determined need to be down with black folk by chanting "Harambee" and letting Huey run the school's Christmas play. Obviously, Riley's reasoning for stalking Santa Claus (above) is the exact thing a thugged out little boy would do if they never got what they wanted for Christmas. It pairs everything you love and hate about the holiday season and wraps it up in a nice, red bow.—khal

13. A Date With The Health Inspector (Season 1, Episode 5)

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Air date: December 4, 2005

As if casting Charlie Murphy to voice a white, rich and entitled wannabe thug wasn't enough, now Samuel L. Jackson is his equally Caucasian parter-in-crime?! The adventures of Ed Wuncler III and his pal Gin Rummy take center stage in an episode centered around Tom DuBois' very understandable prison phobia. Because, you know, prison leads to anal rape. But it's not all fake Superthugs and rape jokes. Peep the way super rich white dudes Ed and Gin use the mission to exonerate Tom as an excuse to rob, terrorize and intimidate. White privilege at work, no matter who's ass is on the line. (Always remember, though: the absence of evidence is not the evidence of absence.)—Frazier Tharpe

12. Thank You for Not Snitching (Season 2, Episode 3)

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Air date: October 22, 2007

You come to The Boondocks for smart, hilarious takes on issues within black culture, both current events (R. Kelly's trial) and evergreen shit like "the itis," or in this case, snitching. With the cast of characters that comprise this world, from the straight-laced black guy to a devout practitioner of the hood code like Riley, it is quite simply the perfect issue to see this show take on and oh boy does it deliver.

Ed and Gin Rummy buffoonery, an amped up neighborhood watch and Riley's street ethics coming back to bite him in the ass? The fact that this isn't a top episode of the series is just further proof of how great this show really is.—Frazier Tharpe

11. Guess Hoe's Coming to Dinner (Season 1, Episode 3)

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Air date: November 20, 2005

Essentially, this is the song "Gold Digger" rendered as an episode of The Boondocks, and you even hear a brief snippet of Kanye's song once Granddad has fallen in love with Cristal, spelled and pronounced just "like the champagne." After a ride home from the grocery store where the couple met, Riley asks, "You do realize that light-skinned ho was a ho—right, Granddad?," and then Huey delivers his iconic "game recognize game" rebuttal of Granddad's charisma and impoverished rant about Red Lobster's acclaimed Cheddar Bay Biscuits. It's crazy how quotable ("fake-ass Mariah Carey!") this episode is before A Pimp Named Slickback, voiced by Katt Williams, arrives in the final minutes to collect his girl and her due. "Lord, please pray for the soul of this bitch. Guide my pimp hand, and make it strong!"—Justin Charity

10. A Date With The Booty Warrior (Season 3, Episode 9)

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Air date: June 27, 2010

The Boondocks was at its best when it peeled away layers of black American life. The show tirelessly worked to lay bare everything black Americans thought or feared, no matter how embarrassing or ungainly. Enter the Booty Warrior. Pulled from an episode of Lockup, the Booty Warrior was an inmate named Fleece Johnson who made national news by proclaiming that “booty is more important than water.” It was funny then, but when used as a device to discuss the prison industrial complex as well as the school-to-prison pipeline, as well as continue Tom’s fear of going to prison, it turns to gold.

When Aaron McGruder announced he was no longer going to produce the show, he said of The Boondocks that “it was important to offend, but equally important to offend for the right reasons. For three seasons I have personally navigated this show through the minefields of controversy. It was not perfect. And it definitely was no quick. But it was always done with a keen sense of duty, history, culture, love.” Episodes like this, that touch on so much potentially offense topics while trying to educate, are testaments to that vision.—Damien Scott

9. The Fundraiser (Season 3, Episode 7)

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Air date: June 13, 2010

The episode begins with a ghastly synth pulse that invocates Giorgio Moroder's film score for Scarface. This is one of the strongest Riley-centric episodes, in which Riley launches a Young Reezy's Fun-Raiser as a candy-shilling monopoly and money laundering front. It culminates with a famously vulgar, anti-Brit diatribe that's perhaps the single most gratifying minute of The Boondocks: after losing Grandad to a car bomb planted by a rival chocolate operation, Riley confronts Mr. "Willy Fucking Wonka" with a burst of articulate disrespect of Guy Ritchie, Queen Elizabeth, and the NHS.—Justin Charity

8. The Itis (Season 1, Episode 10)

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Air date: January 22, 2006

Huey: "This food is destructive!"

Granddad: "This food is your culture!"

Huey: "Then the culture is destructive!" 

Riley calling Mrs. Dubois' peach cobbler "throw up with peas in it," Tom Dubois lounge-singing Biz Markie at Granddad's restaurant, and Huey breaking down the irony of the movie Soul Food ("They get together for a Sunday dinner and eat the same food that just killed Big Mama!") are the highlight jokes, but the essence and message of this episode can be found in that exchange between Huey and Granddad. Having pride in your culture is a great thing... as long as it isn't slowly poisoning you.

Interesting too is Mr. Wuncler clarifying that "the health food thing attracts the wrong crowd," and saying he needs to be thinking "urban, negro, the black thing" before he opens Granddad's soul food restaurant. Ed Wuncler understands that people who eat healthy tend to make smarter choices overall and are disproportionately politically aware—two things that are bad for business. Wuncler knows Granddad's Itis-inducing meals are the quickest route to cash, and couldn't care less as the food destroys the entire community. 

As usual Huey tries to talk some sense into everyone, but is called a white boy for being "too good" to eat stuff like "sausage and waffle and fried chicken breakfast lasagna" and "bacon-wrapped chitlin-stuffed catfish." Huey bringing Elijah Muhammad's How To Eat To Live to Granddad's restaurant proves he couldn't be farther from a "white boy" and that eating healthy isn't an exclusively Caucasian phenomenon. "The Itis" overall is one of the preachier Boondocks episodes and at times feels like an 18-minute version of Dead Prez' "Be Healthy," but still. A lounge version of "Make The Music With Your Mouth, Biz"? That shit's funny.—Maurice Peebles

7. The Hunger Strike (Season 2, Unaired)

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Air date: n/a

This is my absolute favorite episode because I hate what happened to BET with a passion. I was done with them when they deaded BET Nightly News, Rap City the Basement, and other enjoyable programs for more ignorant heavy programming like Hell Date and bootleg MTV reality shows. Aaron McGruder felt the same way and decided to make a satirical episode taking aim at the once influential channel. BET’s CEO Debra Lee is depicted as the head of an evil organization out to destroy black people and Huey goes on a hunger strike to thwart their plans. On his journey, he links up with Reverend Rollo Goodlove, an Al Sharpton type that knows a good PR opportunity when he sees one. As Huey’s protest gains national attention Debra Leevil decides to offer Rollo a show and hired Uncle Ruckus after her white master asks her to handle the boycott.

The underlying messages? As long as whitey owns BET it won’t change, niggas just gonna be niggas, and don’t make an episode dissing a channel under the same Viacom umbrella as your show.—Angel Diaz

6. The Story of Thugnificent (Season 2, Episode 5)

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Air date: November 5, 2007

Season two is when every black actor, comedian, rapper, and brand co-signed The Boondocks and made several cameos as voice actors. "The Story of Thugnificent" assembles Snoop Dogg and Busta, Fat Man Scoop, Sway, Nate Dogg, and Xzibit for a spoof of Atlanta rap and the DVD beef culture of the mid-00s. (These themes recur in the Gangstalicious arc.) When Thugnificent and his Lethal Interjection Crew move to Woodcrest, Granddad complains to the local news and thus sparks a generational rivalry and, inevitably, a noise complaint. Thugnificent, Snoop, Busta, and Nate Dogg drop as posse diss titled "Eff Grandad," with a music video crafted to evoke the effigy comedy of Eazy-E's "Real Muthafuckin G's."Justin Charity

5. The Garden Party (Season 1, Episode 1)

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Air date: November 6, 2005

A militant black kid, his thug-fetishizing younger brother and their eager-to-max-and-relax grandfather move to the suburbs...of COURSE the pilot has to send the nouveau-riche brothas to a lily white garden party and unleash the hilarity. But while the way Huey tries and fails at scaring Yuppies is low-key brilliant, the episode is far from showcasing the best of what The Boondocks would go on to offer. That is, until Uncle Ruckus, resentful at the Freemans for living up to their surname while he toils like an indentured servant, drunkenly sings an impromptu diss track titled "Don't Trust Those New Niggas." The self-hate is so palpable its hilarious, better yet is when the white audience claps because "I think that word's ok when 'they' say it." Welcome to The Boondocks, dissecting one contemporary race interaction at a time.—Frazier Tharpe

4. Tom, Sarah and Usher (Season 2, Episode 2)

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Air date: October 15, 2007

It’s the little things that made The Boondocks such an alluring show. When you weren’t falling into the beautifully intricate backdrops put in motion by MOI Animation, you were picking up on little ad-libs, references, and nods that seemed sprinkled all throughout Aaron McGruder’s, Rodney Barnes' and Angela Nissel’s scripts. It’s those little things that made the second episode of the second season one of the most memorable.

"Tom, Sarah, and Usher" takes a break from assessing pervasive racial imbalances and instead focuses male ego. After running into Usher at a restaurant, Tom accuses Sarah of being wild thirsty. Sarah balks and the two go on a break. Tom moves in with the Freemans, who then enlist the help of A Pimp Named Slickback. Hilarity ensues. But, back to the little things. The highlight of the episode comes when Tom, alone at the Freeman’s house, decides to sing a rendition of Usher’s "Burn," taking to the streets to dance with some neighbors. In the care of any other animated series, this would have been a clean cut performance, but McGruder and Barnes managed to infuse the scene with humanity: Tom sings a little off-beat, a little too stiff, and really off-key. He adds words that aren’t there, stumbles and mumbles over others. He takes the streets to perform with neighbors in the rain and pause when a car drives through playing a Thugnificent song. When Sarah calls and he tries to play it cool, she asks, “Are you doing the music video thing again?”

They’re all little things, but they’re hilarious, and they make up the show.—Damien Scott

3. The Trial of Robert Kelly (Season 1, Episode 2)

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Air date: November 13, 2005

This is a very important episode. Personal responsibility and obsession with celebrity are issues that plague America. On the show’s second episode the creators decided to tackle both.

By all accounts, R. Kelly is the pied piper of R&B, a man whose musical genius buries his alleged fetishization of minors in the darkest corner of the biggest walk-in closet. He’s the black community’s Woody Allen, if you will. Riley takes the side of personal responsibility when it comes to being old enough to realize whether or not a person is old enough to willingly be peed on. He argues that a 14-year-old is old enough to make that kind of choice. Dave Chappelle touched on this very topic a few years before this episode aired during his standup special For What It’s Worth. On the flip side, Huey feels like Kelz’s celebrity shouldn’t save him from paying the piper. At the end, Riley won and Huey came to grips with the fact that you have to support your people even if they can be a little ignorant.—Angel Diaz

2. The Story of Gangstalicious (Season 1, Episode 6)

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Air date: December 11, 2005

Riley: "Gangstalicious got shot!"

Granddad: "Again?"

Riley: "We got to do something!"

Huey: "I got an idea! Let's go to we don't end up like Gangstalicious."

If there's nothing else you remember from this episode, this is it. Shit, in my opinion, this brief section of conversation could be used as a microcosm for the entire show. Riley is caught up in the moment-to-moment absurdity of hip-hop culture that sometimes takes up too much mental real estate for black folks, and Huey, as usual, is the less popular voice of reason and perspective. "Gangstalicious got shot!" could just as easily be subbed for any present-day rap beef, reality TV star drama, or internet-generated athlete scandal. Example:

Riley: "50 said he ain't backing down from calling 'Empire' gay!" 

Huey: "I got an idea! Let's go to we don't end up caring what 50 Cent thinks about a fictitious hip-hop family."

Gangstalicious, we learn, is a complete phony. He is not a gangsta. He is not a heterosexual. He is nothing like the hyper-thug masculine persona he presents publicly. And—because of these things—he is hip-hop. Which is part of the larger truth the show's creator Aaron McGruder presents in this episode. Rappers—as well as many celebrities in general—are fake as hell. And until we all wise up (in Huey's example by going to college), dumb, insecure, trend-hopping niggas like Riley will always easily separated from their money by paying them attention. THAT'S why this is one of the all-time best episodes. Well, that and Mos Def's Gangstalicious voice.—Maurice Peebles

1. Granddad's Fight (Season 1, Episode 4)

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Air date: November 27, 2005

When The Boondocks is on, it's REALLY on, and it hits on a number of different levels. We're talking socially conscious topics mixed with the show's lore that are hilarious as hell and speak to the honesty of black culture. Nothing is more representative of all of those traits than "Granddad's Fight."

The beginning of the episode breaks down "nigga moments," a.k.a. those times where normally rational black males get agitated and wild out. It's a situation that many black men will identify with, but didn't have a proper name for. How does the "nigga moment" manifest itself in the show? Granddad getting into a wild fight with one of the most insanely memorable characters in the Boondocks universe, Stinkmeaner—over some sneakers, no less. It's not often that an ornery, blind old man gets the kind of shine Stinkmeaner, becoming a recurring character throughout multiple seasons. He also beats the shit out of Granddad, who gets some tragic revenge.

The best part? The term "nigga moment" is now in the pop culture lexicon with a hilariously vulgar tale, tying in everything that makes The Boondocks such a great and impactful slice of television history.—khal

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