Riley, Granddad, and Huey, the three main characters of 'The Boondocks'

Riley, Granddad, and Huey, the three main characters of 'The Boondocks'

Adult Swim

The 13 Best 'The Boondocks' Episodes of All Time

These are the best The Boondocks episodes, from "The Story of Thugnificient" to "Smokin’ With Cigarettes."

When The Boondocks ended its nine-year run on June 23, 2014, a void was left in television. In the years following, a lot has happened concerning the television series. A potential revival of the show was set to take place after WarnerMedia picked up The Boondocks in September 2019. However, it was revealed that the reboot was canceled in early 2022. Gary Anthony Williams, the voice of Uncle Ruckus, mentioned that the reboot was canceled because it took too long to produce.

After its 2005 premiere, The Boondocks became more than a satirical animated series for adults. Based on the daily syndicated comic strip by Aaron McGruder, it manifested a specific kind of Black novelty within pop culture.

The antics of the Freemans — consisting of civil rights activist Robert aka Granddad (voiced by John Witherspoon), and his two contrasting grandsons, the militant, Black liberator, Huey, and hotep-in-training, Riley (both voiced by Regina King) — came as metaphorical wake-up calls. These wake up calls (usually brought to light through Huey’s annoyed outbursts at the public) resembled mastery of dialogue in a Spike Lee joint mixed with humor and futuristic horror à la Black Mirror in navigating Black America at the intersection of entertainment and history. Each script incorporated was not only cognizant of brewing culture wars, outlandish antics, evergreen jokes, and managed to foreshadow a lesson or two in the end.

Tragedy struck The Boondocks community in October of 2019 when the show's star and legend of the film industry John Witherspoon passed away at 77 years old. Witherspoon voiced Robert, known commonly in the show as Granddad throughout the entirety of the series' tenure. This news came just months after Witherspoon himself announced the return of the show of the Joe Rogan podcast.

Even if the show never returns, the legacy still lives on (mostly through memes.) Here are the 13 greatest episodes of all time.

13. “Let’s Nab Oprah” [Season 1, Episode 11]

Airdate: February 12, 2006

Targeted Subject: Clout chasing

"Oprah Winfrey has the power to lay waste to the entire industry with a mere utterance! She's a completely invincible, unstoppable force of nature… "- Gin Rummy

Who would believe in successfully kidnapping one of the richest and most noticeable Black women in the world in order to “control bitches?” How about Ed Wuncler III (voiced by the late Charlie Murphy), who's the grandson of Woodcrest’s billionaire realtor, and his best friend and accomplice, Gin Rummy (Samuel L. Jackson). Of course, an eight-year-old Riley wants to join in on the shenanigans of the gun-toting, shoot first, ask questions later duo — especially after taking a liking to them in the series pilot, “The Garden Party.”

Huey tries to foil that plan — which spoofs aspects of Pulp Fiction — but ends up duking it out against his little brother and Oprah’s fictionalized bodyguard, Bushido Brown. The trio doesn’t end up kidnapping Oprah, but rather Maya Angelou at the wrong book signing. And then Bill Cosby — just to return him back for being too annoying.

12. "The Itis" [Season 1, Episode 10]

Airdate: January 22, 2006

Targeted Subject: Health and bad eating habits in the Black community

"This place used to sit between a coffee shop and a day spa — now there’s a liquor store and a damn Footlocker!” - Huey Freeman

Taking its title after a popular term used to describe sleepiness after eating a large meal, “The Itis” ends up being the name of Granddad’s restaurant. Residents of the predominantly white Woodcrest flock in droves to eat Granddad’s soul food, with the added perk of lounging and napping on the beds they’re served in. Eventually, these loyal customers start to become too gluttonous and lazy. Eventually, The Itis has to close because of pending lawsuits and a fatal heart attack of its first customer.

11. "The S-Word" [Season 2, Episode 11]

Airdate: January 21, 2008

Targeted Subject: White people saying the N-word

“You both say the N-word all the time.” - Huey

“I do not.” - Granddad

“Riley thought it was his name until he was three.” - Huey

The Freemans find themselves in the middle of the “N-word” debate when Riley’s third-grade teacher, Mr. Petto, repeats what his pupil said to him after misbehaving in class. What’s ironic is while Riley stands his ground, he has a history of saying the word as a catchphrase and has witnessed white men, Ed and Rummy, say it on multiple occasions.

In the news report montage that opens the episode, there’s a debate on the meaning of the “-er” and “-a” ending and the confusion behind its consistent usage in rap music. Reverend Rollo Goodlove (Cee Lo Green) takes up a lawsuit and media campaign for The Freemans, even debating his frenemy Ann Coulter (who turns out to be a fake, extremist right-winger for pay). In the end, Mr. Petto gets to return back to teaching after only ten days of unpaid leave.

10. “The Fried Chicken Flu” [Season 3, Episode 11]

Airdate: August 1, 2010

Targeted Subject: Groupthink and national panic

"Unfortunately, there is no cure for the pandemic we now face. But we do have an even more powerful weapon — compassion for our fellow man." - President Barack Obama

In December 2018, social media had various takes on the Netflix original movie, Bird Box. The premise of the filmrevolves around an apocalypse that ensues due to a mysterious creature attacking groups of vulnerably curious people. Eight years prior to the release of that film, The Boondocks had its own Bird Box as a result of KFC’s newly released 13 spices chicken. While everyone in the world is dying from eating the chicken, the Freemans are forced to hunker down with rationalized food and supplies with their neighbors, the Dubois family, Uncle Ruckus, Thugnificient, and Leonard. At the end of the Boondocks' episode, they all survive the outbreak which is revealed to actually be salmonella.

9. "Guess Hoe's Coming to Dinner" [Season 1, Episode 3]

Airdate: November 20, 2005

Targeted Subject: Gold Diggers, Sex work, and Misogyny

"Cristal, that sounds like a stripper name. Might you be a stripper, Cristal like the champagne?” - Huey

“And what would you know about strippers little man?” - Cristal

“Not much, but I do know they're usually named after liquor." - Huey

A running subplot in this series is Granddad’s dating life, and his many incompatible, younger paramours. There was Luna, a psychotic kung-fu master from season two; Ebony, his most likely soulmate from season thre; and Kardashia, a knock-off Kardashian from season four. However, none of them compare to Cristal, who is, according to Riley, a “fake ass Mariah Carey” lookalike who takes full advantage of being spoiled by her sugar Granddad(dy). Huey and Riley notice that Cristal exhibits the behavior of a stripper with a criminal past; and, sure enough, that’s confirmed when Katt Williams cameos as A Pimp Named Slickback.

8. "It's a Black President, Huey Freeman" [Season 3, Episode 1]

Airdate: May 2, 2010

Targeted Subject: My President is Black!

“If the election is fake, then what’s really going on?” - Werner Herzog

“The end of America” - Huey

When German documentarian Werner Herzog shows up to Woodcrest, he meets a skeptical Huey whose indifferent about the hype of Barack Obama’s presidency. In the beginning, Herzog learns the apathy comes from Obama “denouncing, repudiating, and condemning” Huey whose labeled a domestic terrorist during the 2008 election. Everyone else in Woodcrest— aside from Uncle Ruckus— are excited for a Black President. Thugnificent, who had no clue about Obama prior to learning his ethnicity, even goes against his brand by joining’s anthem “Dick Riding Obama.”

However, as years settle into Obama’s term, the citizens of Woodcrest learn about how voting on just identity politics can result in legislation they don’t align with (ie Granddad having to pay higher taxes). Through all this, Huey is still indifferent on American history made.

7. "Smokin’ With Cigarettes" [Season 3, Episode 6]

Airdate: June 6, 2010

Targeted Subject: Kids Who misbehave and meet viral stardom

"It’s fun to do bad things" - Lamilton Taeshawn

Riley often loves to do bad things out of sheer boredom as an eight-year-old, but he proved he couldn’t hang with his classmate Lamilton Taeshawn, a spoof of the real-life “bad kid” Latrian Milton. Lamilton enjoys joyriding, attacking his grandmother for not ordering the right chicken, and “smokin’ wit cigawettes.” When Riley learns he has to break away from his newly bad influence by Robert’s belt-whooping commands, Lamilton becomes even more obsessive and controlling about their friendship.

6. "The Story of Thugnificient" [Season 2, Episode 5]

Airdate: November 5, 2007

Targeted Subject: Generational Gaps

"And I started thinking to myself, 'damn what did he do to make them niggas that mad?'" - Thugnificient

Chances are any Twitter user that’s stumbled upon an intense fight video on the platform and then searches through the comments have seen the above quote in meme or gif form. This hilarious sound clip happens less than a minute into the episode when Thugnificient recounts to MTV’s Sway Calloway a fatal shooting, stomping, and “dump” he witnessed on his hometown block. The rapper hails from Terra-Belle, Georgia, which is the third world polar opposite of the city’s meaning, “Beautiful Earth.”

Thugnificient’s move to the upper-middle-class Woodcrest is a swift change of pace for his neighbors who are fans and granddad who is not. As a result, Thugnificient starts a rap beef with the diss track and video “Eff Granddad" (featuring Nate Dogg) after Robert files a complaint about the rapper’s excessive house parties.

5. "The Story of Gangstalicious Part 2" [Season 2, Episode 13]

Airdate: February 4, 2008

Targeted Subject: “The Gay Agenda,” Masculinity, and sexuality in Rap

"The following is a work of fiction. Any resemblance to actual gay-ass rappers is coincidental. Seriously, we're not talking about anybody at all." - Opening credits

At the core of some controversial moments on The Boondocks is the series’ unabashed attitude at confronting homophobia in the Black community. From Riley having the signature catchphrase “y’all niggas gay” being “no homo” adjacent, to witnessing his favorite rapper, Gangstalicious, kiss an ex-homie at gunpoint in Season one. After surviving that nearly fatal attraction, Gangstalicious has graduated from “Thuggin Love” to his new hit “Homies Over Hoes.” Soon, Thugnificient buys into the popularity of the single, which leads to Gangstalicious starting a fashion line with more feminine silhouettes and designs. Granddad fears Riley could be gay, while his grandson is actually disappointed he’s the biggest fan of a semi-outted rapper still in the closet.

4. "The Color of Ruckus" [Season 3, Episode 14]

Airdate: August 8, 2010

Targeted Subject: Uncle Toms

"Nigga, did I just catch you having fun?" - Mr. Ruckus aka Uncle’s father

Up until this episode, it was never fully explained why Uncle Ruckus was racist towards his own people, especially with his dark complexion. He had mentioned having “revitiligo,” a case of going from white to back á la Benjamin Button, but with skin tone. In this episode, Ruckus is vulnerable about his deep-rooted hatred against himself, as his family visits right before his grandmother dies. Rooted in similarities to The Color Purple and Precious, the story of Ruckus enduring domestic abuse at the hands of his overworked father and appreciation of white culture from his black mom explains why the antagonist has no issue with using the “-er” ending and launching bricks at black leaders.

3. "Granddad's Fight" [Season 1, Episode 4]

Airdate: November 27, 2005

Targeted Subject: Black on Black violence

"Webster’s defines the nigga moment as a moment when ignorance overwhelms the mind of an otherwise logical negro male. Causing him to act in an illogical, self-destructive manner, i.e. like a nigga." - Huey

This Boondocks episode teaches viewers the origins of a “nigga moment.” Examples include when two black men bump into each other while crossing the street, resulting in a shootout, or a chair being flung at Eat Dirt during a hip hop award show. In the case of The Freemans: a blind and menacing Colonel H. Stinkmeaner parks into Robert’s car and steps on his new Nikes. After that altercation, Granddad turns into the viral laughing stock of Woodcrest as he missed his punch and falls on the pavement. Although Granddad trains up for their next public fight which draws a ticketed audience, he ends up accidentally killing Stinkmeaner. Of course, the villain’s ghost returns back once every season to continue haunting the protagonists.

2. "The Trial of R. Kelly" [Season 1, Episode 2]

Airdate: November 13, 2005

Targeted Subject: R. Kelly…

"We all know the nigga can sing but what happened to standard, what happened to bare minimum? You a fan of R. Kelly? You wanna help R. Kelly? Then get some counseling for R. Kelly…But don’t pretend the man is a hero.” - Huey Freeman

During the press run and social media firestorm revolving around Lifetime’s Surviving R. Kelly docuseries in January 2019, The Undefeatedreached out to Aaron McGruder. This Boondocks episode perfectly captured the tension between “Free R. Kelly” supporters (Riley being one) and those wanting him locked up (Tom DuBois being the prosecution) during his child pornography trial. It dismantled some hypocrisies of the justice system while also highlighting “the extent niggas love R. Kelly” and were willing to overlook the mountain of reported evidence and allegations.

As shocking as the episode is — including a lampooned court testimony from a 14-year-old “willing participant”— the sobering moment comes when Huey stops a bandit-masked R. Kelly’s lip-syncing performance mid-closing arguments to deliver a monologue about “standards.” When asked about the resurgent relevance of that episode 14 years later, McGruder simply responded: “that’s crazy.”

1. "Return of the King" [Season 1, Episode 9]

Airdate: January 15, 2006

Targeted Subject: Black Society At Large

“Niggas love to hear themselves talk but hate to explain!” - Dr. Martin Luther King Jr.

As the holy grail of Boondocks episodes, this executes one of the best hypothetical situations on how history may have changed. What if Martin Luther King Jr. didn’t die following his 1968 assassination attempt, and instead woke up from a 32-year coma? It would result in him staying with The Freemans to rebuild his brand, after he becomes one of America’s most hated individuals for suggesting to “turn the other cheek” and forgive the country’s foes.

As Dr. King is getting readjusted to life in the millennium age, he experiences BET in it’s “Booty Butt Cheeks” music video era, McWuncler’s using his face to promote sandwiches, and how an urban promotions firm can turn a church into a nightclub. Through it all, Dr. King has had enough and delivers a revamped “I Have A Dream” speech about “Niggas.” He moves to Canada after his words spark a black revolution, and Oprah is elected president. The episode went on the winThe Boondocks a Peabody Award.


Da’Shan Smith is a pop culture writer based out of New York City. You can follow him @nightshawn101