The word "Boondocks" derives from the Tagalog word "bundok" which means "mountain". The word came into American use after the Philippine-American War when returning military personnel used the term. It became a slang word for suburban or rural areas.
The controversial nature of the comic strip (as well as Aaron McGruder's insistence on maintaining creative control) lead to several failed attempts to get this series going since 1999. McGruder initially developed "The Boondocks" as a television series before turning it into a strip. Some of the would-be homes of the series included HBO and MTV. In 2003, the FOX network ordered a pilot with the prospect of picking up the series. They eventually passed, only to have the series taken up by Adult Swim.
Although Reginald Hudlin helped develop the series, his involvement with the show ended in July 2005 (four months before its premiere) when he was named President of Entertainment for the B.E.T (Black Entertainment Television) network (the very channel that he and McGruder have often lampooned).
Ed Wuncler III and Gin Rummy are based on George W. Bush and Donald Rumsfeld. Ed wears a medallion that says "W" which is Bush's nickname and "Rummy" is Rumsfeld's nickname.
Regina King was originally cast as Riley. The producers wanted her to play Huey as well but she refused. She originally read Huey's lines in the recording sessions just as a placeholder until another actor was cast. But the producers managed to convinced King to take the role and she came up with a voice.
In the comic strip, Huey has a best friend named Michael Caesar but he has not appeared in the series. According to McGruder, this is because he has not found the right actress to do Caesar's voice.
The series theme song, "The Boondocks Theme", is a remix of a previously released song by Asheru titled "Judo Flip".
The Freemans live on 327 Timid Deer Lane.
In January 2013, Aaron McGruder launched a Kickstarter campaign to fund a live-action spin-off film starring Gary Anthony Williams as Uncle Ruckus. The goal was $200,000 but the campaign fell short.
The original cold open was a spoof of the opening of Star Wars: Episode IV: A New Hope. Aaron McGruder is a major fan of the franchise and contacted George Lucas to ask his permission. Lucas gave his permission but the opening was not used because McGruder was dissatisfied with the animation.
Gary Anthony Williams improvised Uncle Ruckus' song "Don't Trust Them New Niggas Over There".
According to McGruder, the scene in which Ruckus is jealous of Granddad was inspired by the scene between Brian and Ben in Monty Python's Life of Brian.
Rosa Parks was originally drawn as one of the protesters at the courthouse. But she was deleted due to her death just weeks before the air date. Parks can be seen briefly in the background at the celebration in front of the courthouse.
The three protesters at the courthouse are based on Cornel West, Julian Bond, and Dick Gregory.
When Huey and Tom meet at the courthouse, a man wearing a baseball cap and backpack is seen walking by. This man is based on producer Carl Jones
Huey's speech at the courthouse was the script given to actors who auditioned for the role of Huey.
Stinkmeaner's voice is partially based on Jack Sheldon who is best known for singing "Conjunction Junction" on Schoolhouse Rock!.
Aaron McGruder originally wanted Steve Harvey to play Stinkmeaner. Cedric Yarbrough read the lines during the recording sessions and McGruder decided to let him do it instead.
The original title for this episode was "The Boondocks Infamous Halloween Special" as it was originally scheduled to air on October 29, 2005.
During the Gangstalicious documentary, a graffiti tag that says "SEUNG" can be seen in the background. This is a reference to Seung Eun Kim, director and producer on the show.
The altercation between Gangstalicious and Eat Dirt was supposed to be a silly, childish fight but the animators drew it as a violent gunfight.
Gary Anthony Williams improvised the song that Ruckus sings to himself when mopping the floor.
Huey attends J. Edgar Hoover Elementary School.
Mr. Uberwitz is fired only to go on to become a teacher in African American History at the University of Maryland. This is a reference to the show's creator Aaron McGruder, who graduated from the University of Maryland with a degree in African American History.
Reverend Al Sharpton publicly criticized Aaron McGruder and Adult Swim for this episode. Sharpton felt that depicting Martin Luther King using the word "nigga" would "desecrate black historic figures". He demanded a public apology and threatened to stage a protest against Time Warner, Adult Swim's parent company. McGruder spoofed Sharpton's criticism in subsequent episodes and in the comic strip the show is based on.
This episode aired on Martin Luther King's birthday. Dr. King would have been 77 years old.
Bill Maher agreed to play himself in this episode but he was unavailable to record his lines. Barry Sobel was recording for the next episode "The Itis" and was asked to fill in for Maher.
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