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Maybe it was the memes, or the clips, or because our homie was having his students watch the MLK, Jr. episode at the college where he teaches, but we really found ourselves missing The Boondocks this week. This isn’t necessarily a love letter to the Boondocks going away or what it could’ve been in its waning years. We’ve done that before. Let’s get down to the straight bars about why this show was such a landmark achievement in not only Black entertainment, but animation and social commentary as a whole. Also, you’ll notice that no Season 4 episodes made the list. That shit ain’t by accident. Not only do we do everything in our power to forget that shit happened, but truthfully, nothing from season 4 would even make a top 25 Boondocks episodes, let alone a top 10. So…don’t ask.

Secondly, Boondocks is the kind of show where you can ask 10 people what their favorite episode was and you might get 10 different answers. So if your favorite don’t make our list, tell us what your favorite is in the comments…with more Tom Dubois sentiment than Uncle Ruckus. I mean, fam, no matter the questions you face in life, the answer will always be: Don’t be Uncle Ruckus. Let’s get into it.

10. Let’s Nab Oprah (February 5, 2006)

Season: 1, Episode: 11

“Not so bad? That’s a whole episode of Seinfeld.
It takes us a whole episode of Sein-fucking-feld to rob a bank”- Gin Rummy

This episode had white privilege on fleek. We see Ed Wuncler (Charlie Murphy) and Gin Rummy (Samuel L. Jackson) on an average day, discussing how texting with your thumbs isn’t real technology and robbing banks… horrendously. Riley shines this episode as he displays how quick on his feet he is in persuasion, planning, and adapting to situations as they arise. Those situations being Wuncler and Rummy’s fuck up after continuous fuck up. Wuncler and Rummy getting development was hilarious. The introduction of Bushido Brown damn near steals the show as he faces off against Huey.

This episode holds so much weight in gold due to the quotables. One of the funniest scenes is Huey mocking Riley’s comeback of “Not if I take you down first” as it is the inverse of what Huey just said to Riley. Then you realize that it’s Regina King doing both voices of the Freeman brothers, so she in Huey’s voice is mocking her own voice as Riley. WHAT?! THERE’S FUCKING PHYSICS TO THE VOICE ACTING SHIT BABY! – Omar

9. The S-Word (January 22nd, 2008)

Season: 2, Episode: 11

“Hey after a lifetime of being treated like a n***a, if I catch a break off the word, good for me. Shoot, all the years on this Earth, you know how many times I’ve been called a n***a for free. Back in the day, when I white man called you a n***a, all you could do was run around a corner and cry.” – Grandad

Let’s talk about this genius off the muthafuckin’ top. This episode centers around Riley being called a n***a by his teacher at school, which is a parody (but not THAT much of a parody) of a real situation when a teacher dropped N-bombs on a kid like a World War II pilot. God Bless Da Gawd Fred Willard, who I’m sure was asked to say n***a about 700 times in this episode, then had to go home and kiss his wife and kids afterwards. The most epic shit might be him reading the songs of rap titles all using the word while everyone stares at him in stunned disbelief.

“Outraged” by being the victim of a slur he uses like water, him and Grandad try to capitalize, aka Cut the Check, off of the teachers stupidity. Of course this shit turns on its head when Rev. Rollo Goodlove (CeeLo Green) and Ann Coulter (Jill Talley) collaborate to stir outrage on every major network. This episode puts a lot of shit on its hit list. The debate over who can say it, White outrage, talking heads on TV as opportunists, and the facade of outrage and how it can be profitable. Except for the Freemans’. – William

8. Attack of the Crazy Killer Kung-Fu Wolf Bitch (November 19th, 2007)

Season: 2, Episode: 6

You think I knew she was a killer kung-fu wolf b***h? She ain’t say nothin about no damn Kupate, Kumatoo, Kumite, coon, black coon. Now, just hush. I’m trying to figure out what we’re gonna do… Huey, what are we gonna do?”- Granddad

We’ve been privy to Granddad trying to find someone for the longest. This episode we get all up in his nudes and online dating profile which attracts someone he thinks he can finally make a connection with. Enter Luna, voiced by the uncanny Aisha Tyler. Oh my god where do we even start with this? The fact that Luna spills the whole beans of details that should be reserved for the 5th or 8th date right off the bat. She got 15 wolves and competed literally in the kumite *Kung-Fu Sfx: Waa-Yahh* and killed mad facts cause I mean aye, we all gotta go. I actually think things woulda worked out with Luna had she not whooped Huey’s ass with a demonstration of her White Lotus technique.

How she goin offer a “friendly sparring” match then beat down Huey with no chill, he still 10, yo. That’s not a good look Luna! The rest of the episode dealt with her going to the EXTREMES of finding out why Granddad was lying to her and trying to subtly break it off all the while being egged on by her friend Nicole (Tichina Arnold) to get answers. Don’t even get me started on Huey’s email to Tom telling him to come over and check the place out. Aisha Tyler was straight comedic flames to make not only this episode but Luna stand out in memory as well. – Omar

7. Stinkmeaner 3: The Hateocracy (May 30th, 2010)

Season: 3, Episode: 4

“I lived, you died. I lived, and you diiiiiiiieeeeed.” – Grandad

Fam, you knew we were gonna have at least one Stinkmeaner episode on this shit as the trilogy finally concludes in season 3. You know the tone is set when the episode opens with Grandad (in what we eventually learn is a nightmare), as Stinkmeaner, run up in the spot like Agent Smith and shit. Grandad tells Tom Dubois to run, but Tom is hesitant because the Stinkmeaners have grabbed Sarah. To which Grandad tells Tom, “Come on, you can find another White woman!” Just fucking savage. Stinkmeaner still dead. No resurrected spirit this time, but his crew, the Hateocracy, which is basically if Sanford & Son was a show about an evil troupe traveling the world like Cain on Kung-Fu, comes to avenge Stinkmeaner’s spirit.

Enough bullshittin’ though, what makes this one of the best episodes is the straight up murda muzik in the fight scenes. They pay homage to so much media. Old-school martial arts films, Naruto, Cowboy Bebop, and others. Crabmisers long-range weapon and sound effect comes straight from the 1977 film Master of the Flying Guillotine. THERE ARE LEVELS TO THIS SHIT, FAM. Sprinkled with great fight scenes, none are better perhaps in all of Western animated glory than the Hateocracy vs Grand Master Bushido Brown, ending in perhaps the most unexpected and brutal way. “Ain’t it a beautiful day to fuck a n***a up?!” – William

6. The Story of Catcher Freeman (January 28th, 2008)

Season: 2, Episode: 12

“N***a, you trying to get off the plantation by selling a script? (Laughs) N***a, you ain’t even supposed to know how to read. Plus there’s a writer’s strike going on.”

Yo, you knew, you fuckin’ knew that eventually Aaron McGruder and the fam were gonna do some shit on slavery. That shit was inevitable, like waiting for a celebrity to say some racist shit on TV, then apologize on Twitter two days later “if they offended anybody.” But this is why Boondocks was a master class, because lots of people have tried to do some shit like this, but didn’t have the deft touch to pull it off. The three versions of Catcher Freeman between Grandad, Uncle Ruckus, and the “true version” are blended at a genius level, with intricacies depending on who is telling the story (Grandad’s version of the story incorporates references to Batman about 300 years before he existed and Uncle Ruckus describes the slaves as lazy and ungrateful freeloaders).

But the voice-overs of the story kill this more than anything with hilarious commentary on top of commentary. If anything, the writers shed some light on the glamorization of history depending on who’s telling it and the complicated mess that lineage is in United States. There’s one team of producers that could’ve pulled something like this off…and them cats never made it to season 4 together. – William

5. The Fund-Raiser (June 13, 2010)

Season: 3, Episode: 7

“…fuck your yuck-mouth teeth, fuck your hairpiece, fuck your chocolate, fuck Guy Ritchie, fuck Prince William, fuck the Queen. This is America. My president is Black and my Lambo is blue, n***a. Now, get the fuck out my hotel room and if I see you in the street, I’m slapping the shit out of you.

Remember when season 3 got announced and everyone was skeptical like, I dunno, maybe 2 seasons was enough, I hope this shit don’t suck after such a long delay? Then seven episodes in, we were like, “might season 3 be the best one yet?” Well, finally giving Riley the episode we knew he was meant for, a crime drama, was too brilliant on too many levels. Tired of being a loser, Riley decides to take over the school candy bar fundraiser game by giving it more Tony Montana then it ever had. You get a call back to every great crime movie: Scarface, Carlito’s Way, Godfather, any Guy Ritchie flick, and even went left with a pitch perfect Star Wars: Return of the Jedi homage.

There are too many quotables to list, but Riley’s rant to the English crime lord that moves in on his trade is still one of the most gangsta verses of all time. Secondary only to Riley is Cindy McPhereson, the muscle, who not only re-enacts a scene from Raekwon’s Only Built 4 Cuban Linx, but gets a frozen action scene with Riley voice-over straight out of a Scorcese flick. Shit is too gutta, start to finish and only gets more ridiculous as Riley builds his empire. Young Weezy’s Fundraiser, they only want hustlers. – William

4. The Story of Gangstalicious: Part II (February 4th, 2008)

Season: 2, Episode: 13

“But homies? Oh no. A Pimp Named Slickback don’t do shit for the homies. Let me reiterate. Don’t do shit for the homies. Unless the homie wanna walk that stroll and get that money, a homie ain’t gettin’ a goddamn thing. And the same goes for brothers, peeps, dudes, fellas, dunnies, comrades, whatever the fuck n***s is callin’ each other nowadays.”- A Pimp Named Slickback

OH. MY. FUCKING. GAWD. THE GLORY OF THIS EPISODE THO! You had Riley in denial about his favorite rapper, Gangstalicious, being gay, and the discussion of male masculinity and homophobia in hip-hop. This episode was a true critique on gender roles, the culture of hip-hop, and the stigma that comes with one’s sexual preference. There is such a large discussion of social commentary to be had… but I wanna talk about Gangstalicious’ obliviously homo-erotic clothing line that Riley and Thugnificent’s crew were fucking with cause THAT SHIT KILLED ME! Gangstalicious had a fucking clothing line on display on Good Morning America and had a model in an extra long white tee with a square cut out where the ass is saying it’s there to make it easier to grab the burner? I. CAN. NOT. FUCKING DEAD!

The bait and switch of how the gay rumor came back on Gangstalicious and now Thugnificent and his hard-ass friends turn straight soft because by the rules of masculinity if they hang with Gangstalicious and have him on a track that means they’re gay too. These cats were hiding under sofas, the tiger skin rug, and in the indoor pool when Gangstalicious rang the doorbell! Thugnificent saying how weird the shit was going to be made it soooo much weirder and more hilarious. It took an intervention from A Pimp Named Slickback to get Riley to see that Gangstalicious’s “Homie over hoes” song had a very gay message. A pimp (named Slickback) had to tell Riley (who thinks everything in the world is gay) that his outfit and favorite rapper was gay. You can’t write me a better satire man, you can’t write me better social commentary on this one with humor. I don’t believe it. This shit is G.O.A.T. for making us take a look at how far we’ll go based upon rumors instead of just standing up for a friend and who they are. Acceptance is a hell of a drug.- Omar

3. Return of the King (January 15th, 2006)

Season: 1, Episode: 9


Aaron McGrudger gives us a world where the attempted assassination of Dr. Martin Luther King, Jr’s didn’t kill him but left him in a coma. America rejoices as he comes out of it 30 some odd years later but upon stating his opinion of non-violence and love thy enemy when asked about the September 11th attacks, America does what it does best — tear him down. I loved this episode because you know god damn well that is exactly how it would go down if King were still around man. You can’t tell me shit different. White folk wanna talk all about what King would do but as soon as that doesn’t fit the agenda? Media assassination.

King tries to bring the truth back to his people but when his old tactics aren’t working and he looks out at a sea of folk that need to hear the truth he is ignoring, he brings out the frustration from years of turning the other cheek like the wrath of God as he tells everyone to shut the hell up. Once you have Martin Luther King yellin at you, the fuck you goin do? You know you fucked up. King goes on a detailed rant of everything that’s wrong and what needs to be right as he takes shots and the Black community reacts and goes about changing the way things are. A lot of people were offended (in real time) about how Mcgruder had King go off the hook but let’s just be clear man. You know god-damn well there are times when conventional methods don’t work and you gotta take charge, also I would pay money to see ANY civil rights leader step in the booth and be allowed to say the shit they really want to say. Y’all better let that fictitious representation of MLK talk his shit. – Omar

2. It’s A Black President, Huey Freeman (May 2nd, 2010)

Season: 3, Episode: 1

“Now that it looks like Obama is going to win, as a Black African American Negro, are you merely excited or are you extremely excited that everything is going to change forever?” – Werner Herzog

Yo, lets get some shit straight: The cameos on The Boondocks were great. From Samuel L. Jackson to CeeLo to Aisha Tyler to Kat Williams, the guest appearances almost never disappointed. But, when you get Werner Herzog, international documentarian to play himself, recording a documentary about Huey Freeman and his withdraw from Obama-mania, you’re operating on levels of genius not gifted to us mere mortals. As this episode debuted in 2010, I remember thinking how disappointed I was that there was neither a comic strip nor a TV show during the 2008 presidential campaign as I can’t imagine what McGruder could’ve done with those events. The next best thing, the only thing really they could do with that untimely absence was this: a flashback of how the Freemans welcomed the hype.

Besides the incredible 1-to-1 parodies and efficient use of the most spectacular and ridiculous moments from that 2008 race, the most beautiful thing this episode shows is the very real hype, misinformation, true motivations, and then underwhelming sentiment for much of the Black community regarding President Obama. It’s a master stroke and I often can’t believe they fit all that into 20-some-odd-minutes of TV. Highlights that never get old: Jeremiah Wright’s rant, the Herzog and Huey’s interactions, and Will.I.Am and Thugnificent’s “Dickriding Obama” starring a dancing George Clooney. And the Riley Freeman interview. And Uncle Ruckus shotputting bricks at an Obama cardboard cutout. And Grandad trying to get VIP tickets to the inauguration ball with Beyonce. And, and, and. There’s too much good packed into this, definitely one of the best animated displays of social commentary ever created. – William

1. The Red Ball (May 16th, 2010)

Season: 3, Episode: 3

“We’re American. We don’t quit just because we’re wrong. We keep doing the wrong thing until it turns out right.”- Ed Wuncler I

On everything this is the peak Boondocks episode. Ed Wuncler I needs Huey to return to lead his kickball team to victory as he owes Mr. Long Dou and the Chinese mad guap. It’s the senior Wuncler’s actions cheating the game and making Huey believe he crippled another player that took him out the game to begin with. It isn’t until Huey meets Long Dou’s granddaugher Ming that he accepts. Listen, man. We’ve seen Huey in the thick of battle and get tested, right? We’ve never seen Huey in the thick of being an athlete though. Especially in kickball?

Sun, was so good Ed Wuncler had to cheat in order to beat him. Long Dou’s team is full of straight killers too tho, these folks are taking Huey’s team out. The game is just no chill in the least bit, brass knucks, bats, headbutts all that shit is legal in this kickball game. This is the episode with the most injuries in it. This shit made you cringe as you see Ed Wuncler III catch a ball in the chest and get lifted into a wall and crack that shit from impact. KICKBALL IS FUCKING OLD SCHOOL WWF ERA LIT Y’ALL.

Now everybody knows Huey is a fucking problem and they keep telling him to bring back that monster and it isn’t until Huey’s kindness is mistaken for weakness that we see him open the fucking 7th gate and start air-bending ON EVERYONE. Huey is a fucking eliminator through and through sniping cats one by one, until it comes down to just him and Ming. The final showdown is done true anime style as they both unleash their everything. Ming kicks Huey’s pitch with such force her shin breaks. Huey’s wrist breaks trying to catch the ball. It is fucking pandemonium but we see just how far these two go for victory.

Ming crawling toward first base and her aspirations to become the best by beating Huey. Huey seemingly raising from the dead and taking the smoldering remains of the kickball toward a damn near crippled Ming to tag her out. It doesn’t get anymore trill in action than “The Red Ball,” I fucking promise. Huey Freeman proved he’s the same beast and a different fucking animal when it comes to the sport of kickball. – Omar

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  • Show Comments

  • Robin

    Great list and details about the importance of each episode. Not all od these are my personal favorites but that doesn’t matter, this was still great.

  • Sid64ish

    The MLK episode is forever my JOINT. I need to work it into a lesson one day.

  • Amber

    Great list but I gotta put up “The Itis” episode. Amazing commentary on gentrification.

  • Clemic Lewis,Jr.

    i gotta get season 3 on DVD.

  • Umi Ebon

    Soon as you said “no season 4”, I was like, “say no more”. IDGAF what the list looks like, long as you tell me that. Kind of wish the list was bigger, the first three seasons were just gold. Honorable mentions have to go to gentrification allegory episode “The Itis”, “The Passion of Reverend Ruckus”, “Hunger Strike”, “Stinkmeaner Strikes Back”, and “It’s Goin’ Down”.

  • Wa Sabi

    The blind n***a samurai

  • Nigel Wade

    This is why I love this site. I KNEW I recognized that fighting sequence in Stinkmeaner 3 but couldn’t remember where. *golf clap *

  • VyceVictus

    I know Season 4 was trash, but i gotta go to bat for “Breaking Granddad”. When Granddad tries to sell the explosives-come-hair relaxer on the black market and Huey tries to warn of the danger, the Boss Lady’s response is so real it hurts: “These bitches would put napalm on they hair if it make it straight”

  • Leonce

    When I got to entries 5, 4, and 3, my heart started pounding a little because I didn’t see my favorite ep yet, but there it was, nestled comfortably at number 1, The Red Ball. Excellent list, but really, you can’t miss with those first three seasons.

  • Derrick

    I would add “A Date With The Health Inspector” (Season 1)

    It goes in on the War on Terror in the most clever of ways: The Introduction of Rummy (a Donald Rumsfeld knockoff). The X-Box Killer search (the Hunt for Bin Laden). The gas station owner who looks like Saddam Hussein. The rising gas prices. The list goes on.

    This episode is a prime example of The Boondocks at its finest.

  • JAM Renaissance

    I wanna say y’all missed “A Huey Freeman Christmas” and “Stinkmeaner Strikes Back”, but man… I don’t know what I’d take out.

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