Top 20 Funniest Boondocks Moments

“Stinkmeaner Strikes Back”

This moment still continues to make us laugh so many years later. It occurs after the spirit of ‘ol Stinkmeaner rises from hell. In order to spread chaos, he takes possession of attorney Tom Dubois. When the legal man is cheated out of a parking space at the last minute, he gets angry… but starts to back down. But then Stinkmeaner’s spirit takes hold and makes Tom dropkicks the aggressive offender in the chest. After executing this hilarious martial arts move, we’re treated to a relentless barrage of insults. While Tom doesn’t remember what happened at first, we’ll never forget this parking lot scene.

“Riley Wuz Here”

“The Boondocks” had a way of making brilliant satire while producing genuinely emotional moments. A great example comes when they elevated what could’ve been a one note joke about a famous artist into a fantastic punchine. While Riley is doing graffiti, a walking Bob Ross parody shockingly walks up and gives the kid advice. The two begin working together to tag more places around town. Watching the soft spoken art teacher calmly encourage graffiti and other crimes never stops being funny. And despite his calm demeanor, he’s willing to shoot at police tires. This humorous plot culminates in a heartwarming moment where Riley reveals a piece he made for his family…before being ordered to clean it up.

“Tom, Sarah and Usher”

A boring anniversary for Tom and his wife Sarah is rocked when Usher arrives. An impromptu serenade and flirting from the famous singer drives a huge rift between the couple. After the spouses split early in the episode, a distraught Tom sings a rendition of Usher’s “Burn”. His rendition is both incredibly off-key and laugh-inducing. At one point, Tom even forgets the words to the song! What makes this impromptu musical number even better is the animation. It’s treated like a perfect parody of Usher's music video. However, the show constantly reminds the depressed man that he’s acting like he’s on camera while everyone else is going about their lives. This sequence is so entertaining that we might like Tom’s “Burn” more than the original.

“Let’s Nab Oprah”

Ed Wuncler III and his partner Gin Rummy hatch an ill-advised plot to make Oprah Winfrey their hostage by getting to her at a local book signing. But it predictably goes pear-shaped right from the jump. For starters, they go into the wrong book store and don’t grab the influential female celebrity they were looking for. However, their scheme only goes further off the rails from there. After reorganizing the plan, they once again get control of the wrong person. The duo commits all these mistakes while Riley constantly heckles how bad they are at executing a plan. By the end of the episode, their ill-fated scheme only succeeds at making us laugh.

“Attack of the Killer Kung-Fu Wolf Bitch”

While Riley and Huey’s Granddad tries his luck with a lot of women, there was one person in particular that nearly spelled his doom! After Robert Freeman takes another shot at online dating to find someone, he finds the beautiful, intelligent, and charming Luna. But she’s not nearly as nice as she appears to be at first. The red flags start emerging when they realize that Luna’s a master of deadly martial arts. Although Robert tries to make a clean break, she returns to the house and threatens the family’s life. While the end of the episode is extremely bleak, the main story serves as an incredibly over-the-top cautionary tale about online dating.

“The Story of Gangstalicious”

The character of Gangstalicious is a great parody of the hardcore personas that some rappers create for themselves. His lifestyle takes him to the hospital in a wildly unexpected way. Shortly after the musician insists he won’t get shot again, the news cuts in and says he’s wounded. The sudden announcement would’ve been funny on its own. But the ironic twist gets better when we see how Gangastilicious got his injury. While singing a song called “I Got shot” at a concert he gets…well, you can guess the punchline. This great gag comes with a great button that the audience doesn’t get the musician help right away because they think it’s all part of the song.

“The Story of Catcher Freeman”

Since “The Boondocks” was unafraid to tackle taboo subjects, the show spent an episode dedicated to telling the story of a black man named Catcher Freeman who lived before the Civil War. Both Robert and Uncle Ruckus tell their own wild and ludicrous version of this man’s history. However, the truth is much more of a joke than either of them could have expected. It turns out that Catcher wasn’t the noble hero Grandad painted or sinister villain Uncle Ruckus suggested. The historical figure was simply concerned about getting a screenplay produced while events around him spun wildly out of control. While this plot goes to ridiculous lengths that will still make viewers gasp, the understated ending of the episode is the best punchline.

“Return of the King”

Rosa Parks was forever etched in the history books when she refused to give up her seat for a white passenger on a bus. But in this infamous flashback, Grandad suggests we don’t know what really happened. He claims that the bus driver asked him to move first. After Robert refused, Rosa Parks followed suit and said she wouldn’t give up her seat either. In the aftermath of their protest, Grandid claims that no one remembered that he was there at all. While this seat mishap sounds like your average “Seinfeld” joke, it becomes an absurd moment of satire in this historical context. The speed at which the characters move on from this account only adds to the humor.

“Return of the King”

In one of the show’s most controversial plots, they reveal that Martin Luther King Jr. has actually been in a coma for decades. Although his return is initially met with universal joy and praise, he finds it hard to adjust to the modern world. Martin Luther King’s frustrations about how certain aspects of the world have turned out slowly build up inside of him throughout the narrative. He finally lets his rage out in a cutting monologue that parodies the famous “I Have a Dream” speech. Martin Luther King Jr. hilariously calls out several things he can’t stand. Admittedly, the icon’s frequent use of a certain word still divides audiences today. This boundary-pushing speech remains one of the show’s most controversial bits to date.

“The Fundraiser”

What started as a “Boondocks” episode about selling chocolate turned into a fantastic parody of crime narratives like “Goodfellas” and “Scarface.” Riley goes from hustling a few candy bars at school to building an candy coated empire that spread across multiple schools. After enjoying success, his business rivals resort to increasingly brutal methods to stop the sweet operation. Riley eventually comes face to the face with another chocolate kingpin and launches into a hilariously profane speech…that we can’t play a single second of. Although we can’t dive into it here, it’s definitely worth checking out to see how chocolate led to such an over-the-top monologue.

“The S-Word”

It’s no surprise that the first entry on this list features this pair. In Season’s two’s “The S-Word”, the Freemans sue Riley’s third grade teacher Mr. Petto for using this slur against Riley. Mr. Petto explains that his foul-mouthed student’s language is so heavily littered with the slur that he has stopped noticing it entirely, as it has crept into his inner voice. He depicts Riley’s use of the word as being so ubiquitous that when he heard Riley ask about borrowing a fry, Mr. Petto’s inside voice had the reflex to respond in kind instead of being offended by the contemptuous term! This episode is actually loosely based on real events.

“The Itis”

If you know what it’s like to taste food as addictive as caffeine, then this episode is for you! When Granddad cooks soul food for Sunday dinner, Ed Wuncler is so impressed that he offers to open a restaurant to serve it. Granddad’s food produces an effect called “the itis”, which is a sleepy state that results from its extremely high fat content. Wuncler’s plan (as suggested by Riley) to cater to this effect by providing beds for sleeping customers of “The Itis” restaurant proves to be too successful, as the neighborhood quickly devolves into a crime infested area, with individuals becoming obsessed with Granddad’s fatty food. It is ultimately revealed that this was Wuncler’s plan all along so that he could buy the remaining property in the neighborhood.

“The Story of Thugnificent”

When the fictional rap superstar Thugnificent moves into Woodcrest across the street from the Freemans, a beef is instantly born. Thugnificent makes an immediate impact in the neighborhood by throwing a party, and Granddad files a complaint for noise and cars parked on his lawn. In response to this transgression, Thugnificent releases an expletive filled diss song and music video against Granddad, and it does not disappoint. The rapper goes after Granddad’s old age and snitching ways and hires a pathetic old actor to imitate him. The hilarious track then inspires kids all throughout town to assault old people, as a local teen explains “...because Thugnificent does it and that makes it cool."

“A Huey Freeman Christmas”

When Riley doesn’t get what he wants from Santa, there’s a price to pay! In this episode, Riley takes revenge on St. Nick for failing to give him a set of rims that was on his wish list during a previous Christmas. Riley takes it up with the old man in a mall appearance by throwing a chair at him and beating him with a golf club. He then proceeds to threaten Santa in writing, giving us a hilarious insight into Riley’s creative process and making sure to get the point across a few choice words. As we find out later in the episode, the letter doesn’t seem to get the job done to Riley’s satisfaction, so another mall Santa must unfortunately meet the young boy’s wrath.

“The Fried Chicken Flu”

When people start believing that fried chicken might be making them sick, the Freemans turn to President Obama’s televised emergency speech for guidance. After reassuring the country that he and his family are safe, he delivers some unsatisfying news for Granddad. The country’s best way to get through this is to have compassion for our fellow man. Granddad’s panicked anger reveals his absolute distrust and hatred for others as he loudly yells in front of his grandchildren. This makes it abundantly clear that when the apocalypse hits, Granddad isn’t the one you want to be with!

“Stinkmeaner Strikes Back”

If you thought “Reverend Father” Uncle Ruckus would be any less racist than just plain old Uncle Ruckus, then you are in for a surprise! Tom DuBois gets possessed by the ghost of the old man Stinkmeaner, who has returned to seek revenge on Granddad for killing him in a previous episode. Once Stinkmeaner attacks, the Freemans need to use everything they’ve got to subdue him and tie him to a bed. Unable to rid the spirit themselves, they enlist Reverend Father Uncle Ruckus to perform an exorcism, and it goes exactly as you’d expect. Ruckus makes the family beat the possessed man with items like job applications as they scream profanities throughout.

“Granddad’s Fight”

Before Stinkmeaner went to Hell, he caused Hell on earth! He notably got into a huge parking lot scuffle with Grandad. After losing to his enemy’s supposed martial artist skills, Robert Freeman spends the episode preparing for round two. The build up to this geriatric grudge match is absolutely hilarious. But the only thing better than their fight is the punchline. As it turns out, Huey wildly overestimated Stinkmeaner’s ability, and in reality when he beat Granddad he just got lucky. Unfortunately, Huey discovers this too late, and blind man soon meets his demise…

“Guess Hoe’s Coming to Dinner”

When Granddad starts dating a younger woman, you could say that he’s a bit unwilling to accept the truth about her profession. Throughout the episode, his new girlfriend Cristal drops a hilariously great deal of signs to suggest she is a working girl: her ability to run fast in heels, her constant checking to see if he’s a cop, and her multiple shopping trips. Robert’s denial persists, and eventually culminates in a scene in which he meets a man in a purple suit who insists on being referred to as “a pimp named Slickback”. Even after this meeting, Granddad incredulously asks if she really is “a…a...” causing both kids and Cristal to interrupt him by screaming the very obvious answer at him. Talk about rose-colored glasses!

“It’s a Black President, Huey Freeman”

When filmmaker Werner Herzog tracks down Huey to interview him about Obama’s inevitable victory in the 2008 elections, hilarity ensues. Granddad supports the president without having any understanding of what he actually stands for. But while he others rave about Obama’s win and celebrate with a Thugnificent ridiculous track with Will.i.am, Huey is less than impressed. He responds unenthusiastically when asked if he’s “merely excited, [or extremely excited,] that everything is going to change forever”. Herzog’s description that Huey’s bleak outlook is too depressing for him to handle is the perfect way to cap this election episode plotline.

“The Garden Party”

At the top of our list, we have one of the most incisive criticisms of American culture found in the series, and it comes from the very first episode. In a dream, Huey informs a group of rich white people that Jesus was black, Ronald Reagan is the devil, and the government is responsible for 9/11. Pandemonium ensues as the crowd devolves into violent chaos. Later, at Ed Wuncler’s Garden Party that Huey and Riley are forced to attend, Huey tries to re-enact his dream, but he encounters one unanticipated problem: none of the rich white people care. Huey is unable to deal with the encouragement and compliments from the various wealthy party goers, who - instead of being offended and rioting - are all impressed that the young boy is so thoughtful and articulate.