The show debuted in November of 2005 and was instantly a hit as part of Cartoon Network's Adult Swim line-up. Black and white audiences watched every Sunday to see retiree Robert "Granddad" Freeman (voiced by John Witherspoon) and his grandsons, Huey and Riley (voiced by Regina King), and hear their thoughts on Black topics.
Much like South Park, The Boondocks poked fun at Black entertainers, political figures, and current events. McGruder's exaggerated takes on Blackness showcased the absurd while highlighting the need for us to do better as a people.
Though some in the Black community felt the show went too far at times, the series captures the Black Experience in a way no television series, live action or animated, had done before.
A reboot for HBO Max is currently in the works; but until then, let's revisit our favorite episodes from the first four seasons.
Invasion of the Katrinians
The devastation of Hurricane Katrina forced millions of Louisianians to relocate after the loss of their homes. Some stayed in shelters while others moved in with relatives in other states.
Robert Freeman had the unfortunate honor of playing host to his relatives who fled their home state after the storm. Robert's family (voiced by Cedric The Entertainer and Lil Wayne) were unruly house guests infringing upon his personal space and making Riley and Huey's lives miserable.
It's a Black President, Huey Freeman
The election of Barack Obama was a monumental event in American history. Many races and ethnicities rejoiced at the election of the first Black president — but none more than the Black community.
The various real-life reactions to Obama's victory are also the premise for the season three premiere of The Boondocks. Huey isn't nearly as thrilled as Riley and Granddad about a Black president, and their neighbor Tom DuBois (voiced by Cedric Yarbrough) is jealous of his wife's crush on the president-elect.
Riley Freeman's obsession with the life of a gangster is a recurring theme on The Boondocks. His affinity for money, power, and respect elevates him to the status of a chocolate capo in "The Fundraiser."
In this episode, Riley and his crew corner the Woodcrest chocolate market, as Tony Montana did in Scarface. What starts as an innocent competition to sell the most chocolate bars turns into a violent turf war. This episode is notorious for its over-the-top action sequence.
The Story of Thugnificent
Otis "Thugnificent" Jenkins (voiced by Carl Jones) is a multi-platinum rapper from Terra-Belle, Georgia. He and the Lethal Interjection Crew (voiced by Snoop Dogg & Busta Rhymes) recently moved to Woodcrest, and Granddad isn't too fond of his rowdy new neighbors.
The Lethal Interjection Crew takes Robert's not-so-warm welcome as disrespect and records a diss record called "Eff Granddad." Thugnificent's popularity led to multiple appearances in future episodes.
The Story of Gangstalicious Pt. 2
Toxic masculinity and homophobia have consumed Hip-Hop for decades. The genre continues to make strides to be less problematic but still has many miles to go.
In "The Story of Gangstalicious Pt.2," Riley's desire to imitate his favorite rapper, Gangstalicious (voiced by Yasiin Bey), causes others to question his sexuality. Gangstalicious's subliminal messaging suggests he lives a secret lifestyle that his fans haven't discovered.
That's unless you've seen part one.
Guess Hoe's Coming to Dinner
Granddad Freeman is a hopeless romantic. Even though he's in the twilight of his life, he still longs for the embrace of a beautiful — preferably younger — woman.
In "Guess Hoe's Coming to Dinner," Robert falls for a woman in her twenties named Cristal. Blinded by her youthful beauty, Robert is oblivious to her being a stripper and a prostitute.
Huey and Riley do everything in their power to get their grandfather to realize the truth. But he ignores them until Cristal's pimp (voiced by Katt Williams) comes to collect his "property."
No one likes to lose a fight. However, Robert's loss to a blind, cantankerous war veteran Colonel Stinkmeaner made one of The Boondocks's most memorable episodes.
Granddad and Stinkmeaner get into a physical altercation that Stinkmeaner wins. The embarrassment Robert experiences motivates him to train for a rematch. Unfortunately, before Huey can let his grandfather know that Stinkmeaner's win was a fluke, Robert beats him to death — literally.
Return of the King
How would the world look if Martin Luther King Jr. was alive today? According to Aaron McGruder, he'd be disappointed in his image being used to promote capitalism and Black people for losing pride in themselves.
"Return of the King" is a fictional depiction of Dr. King's existence in today's world. After waking up from a coma, Dr. King finds himself questioning what happened to the community he and others like Rosa Parks and Malcolm X worked hard to build.
Not only is this episode a stand-out in the series, but it's also a look at the generational gap that exists in Blackness.
The Story of Gangstalicious
Gangstalicious is Riley's favorite rapper. His gangster image and propensity for beef keep him in trouble with other rappers and in the hospital with bullet holes. Ignoring the demands of his grandfather, Riley sneaks to the hospital to visit his idol.
Riley's trip to see his hero is one disappointment after another. He realizes Gangstalicious's hardcore persona is a sham. He is not the gangster he potrays, and he's also gay. Riley is so traumatized by the series of events that he tries to convince himself it was all a bad dream.
The Trial of R. Kelly
Despite a sex tape with an underage girl making headlines, R.Kelly's career showed no signs of slowing down. In fact, by 2005, Kelly was at the height of his career. The majority of Black people believed he was innocent, while a small percentage had no doubts about Kelly being a pervert.
"The Trial of R. Kelly" is the best episode of The Boondocks because instead of making Kelly a punchline, it held up a mirror to the Black community and made us accomplices to his sex crimes.
Our so-called love for R. Kelly should have seen us holding him accountable instead of ignoring his crimes because of his immense musical talents.
Did we miss an episode you thought should've been on this list?
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