Unknown (possibly 80s or 90s)
Early to mid 20th century
Huey Freeman (grandson)
Robert Jebediah "Granddad" Freeman is the secondary tritagonist of The Boondocks and is the paternal grandfather of Huey Freeman and Riley Freeman. He is the legal guardian of Huey and Riley, after their parents were in some sort of accident, and live in the exclusive suburb of Woodcrest. He is a regular character on The Boondocks cartoon, as well as the comic strip. He is voiced by John Witherspoon. His signature color is jade green. His nickname is "Bitches", which was given to him by Riley in the episode "The Real".
Robert was a Tuskegee Airman and flew a P-51 Mustang, and was an active participant in the U.S. civil rights movement. During the war, his wingman, Moe, often took credit for things that Robert did or that they dually accomplished together, and Robert's angst about this culminated at Moe's funeral, during which he blows the lid off of some of Moe's more embellished accomplishments. Had close relationship with his sister Cookie. Cookie was the smarter and more responsible of the siblings and often called Robert her "Favorite Dumb Ass."
Robert also lived in Alabama during the U.S. civil rights movement. He specifically recalled showing up late for a march because he forgot his raincoat, much to the indignation of his cohorts. He also had a grudge against Rosa Parks for "stealing his thunder", as he was sitting next to her on the bus and likewise refused to give up his seat. The bus driver was only offended by Rosa's, not his, unwillingness to move, however; also, he claims Malcolm X died owing him five dollars. Robert has three different looks as a young man throughout the series.
While living in Alabama during Jim Crow law, Robert was an accidental and unwilling participant in The Freedom Rides. Robert was trying to skip town back home to Chicago but got on the wrong bus with the Freedom Riders. Aftermath of the horrifically dangerous ordeal was Robert doing some jail time with the Freedom Riders leader, Who was of questionable sanity.
Robert's exact age is unknown. But for him to be present during World War II and several civil rights events, he would be 90 to 110 years old today (taking into account his cartoonish antics, his relative stamina and energy versus others his age, and the minimum age of World War II participants - at least 86 per 1945 participation). He obviously was married and fathered a son. The exact fates of his wife, son, and daughter-in-law are unknown but they are considered deceased by all accounts. In the episode Riley Wuz Here, Riley spray-paints a mural on the side of their house of Grandad and his deceased wife on their wedding day, copying a photo from the family album. After Granddad sheds a tear, he thanks Riley and takes a picture of the mural on his digital camera. He then forces Riley to paint over the side of the house.
Robert has been shown to be extremely prideful, impatient and intolerant. He believes in strict discipline, quick to go for his belt when the boys step out of line. As he says "I hate to see a child go unbeaten." He is not exactly the best father figure or influence. He is perfectly fine with sneaking into movies without paying. A dream sequence revealed that he is cowardly and quick to abandon friends and family to save himself.
Robert describes himself as a "Civil Rights Legend." When describing his experiences during those times he shamelessly includes himself alongside several important figures during that period. Quite frankly he earned more animosity from Blacks then he did White people. He also says he's related to Jackie Robinson. According to him the Freeman is silent.
Robert (aka Mr. Bitches) is also a pathological and compulsive liar; Robert is also quite a womanizer with an extremely unhealthy attraction for women significantly younger than he is.
Robert has also been revealed to be extremely incompetent with money and finances. This has lead to him being in debt for two million dollars.
That isn't to say that Grandad is all bad, he has been shown to care for and love Riley and Huey, albeit, he does tend to get embarrassed by their actions or get distracted by other things. He is also shown to have loved his deceased wife, and was touched when Riley painted her on the house.
Robert's combat style focuses primarily on his belt. Because of his experience raising a child (Huey and Riley's father) and then raising Huey and Riley he knows when to use a belt, how to use a belt, and whom to use a belt on. Robert wields his belt in the style of a whip. Robert is shown to use this belt for whupping (normally Riley), restraining (even with no experience he can latch it on people's legs or arms), and offense during a fight. (See Granddad's Whip). Even at a young age, Robert was skilled enough to beat several men down with his belt.
He also uses his cane to fight, also similar to the fighting style of tonfa.
During the episode Stinkmeaner: Begun the Clone War Has, Grandad undergoes extreme training and becomes skilled enough in H2H combat to nearly kill the enhanced Stinkmeaner clone.
Huey for the most part loves his Granddad. But finds it extremely difficult to have any form of respect for him, given Robert's antics and how he can be selfish, prideful and arrogant. Robert often ignores Huey's advice, when Huey tries to warn his grandfather or reason with him not to do anything risky, whether it's a scam he's committing or when it comes to relationships with women, Robert doesn't listen to him and he ends up suffering the consequences in the end, which Huey often has to fix for him even though he's a child. Huey is the only person that Robert did not whup with his belt because of Huey's agility, he is able to dodge it and it winds up hitting Riley, while the other reason is that Huey is more well behaved compared to Riley.
Robert treats Riley harshly because of the way Riley disobeys Robert's authority and how he disrespects him as well as get in trouble in the neighborhood. The rules that Robert sets do not get to Riley which makes him not used to them and Riley is often the reason their house is destroyed from time to time, mainly because of how Riley starts fights with Huey and leaves his brother no choice but to use force to stop him from getting out of control which causes damage to the house. Robert uses physical force to try to keep Riley in line, but Riley is already used to it so it does not change his actions towards Robert, making it difficult for his grandfather. He treats Huey and Riley differently, with Riley even though he physically punishes him from time to time he listens to him more as he and Riley are alike when it comes to wanting things, getting money or when being manipulative. This hints that when Robert was younger he was a trouble maker like Riley as his sister Cookie was the responsible sibling like Huey was.
Robert and Ruckus have a love-hate relationship, where most of Robert's dislike of Ruckus is because Ruckus is very racist towards African-Americans (even though Ruckus is black) and/or any race that is not white. Robert and Ruckus are shown often playing checkers in the park, talking about social issues, women, and black and white dynamics where Robert will often defend the African-American community. Ruckus is seen doing yard work for Robert from time to time, so they may just tolerate each other if nothing else.
Wuncler owns the loan on Robert's house (as he does with every house in Woodcrest). Ed seems to have taken a general liking to Robert, referring to him as "old school". In the episode The Itis he funds Robert's Soul Food restaurant venture seemingly as part of a plot to lower property values in the area so that he could purchase the nearby park and develop it.
The closest thing Robert had to a mutually loving romantic relationship and quite frankly would have been the single most wonderful thing to happen to Robert was Ebony Brown. Robert dated Ebony for a time and they fell in love which each other. But he eventually became paranoid that she was cheating and thought he was not good enough for her. After she does not call Robert for 16 hours he becomes depressed and worried that she left him forever. Riley and Huey tracked Ebony down from information in her Twitter feed. Robert then travels to Malaysia and finds her where she explains she could not call him because her flight was delayed 12 hours and her phone did not work in the airport. While there, Ebony tells him that he does not love himself and kisses him goodbye.
Robert seems to have a soft spot for Jazmine, referring to her as "Little Baby" and often addressing her with a great deal of affection. This is likely due to Jazmine's more innocent and childlike nature, something both Huey and Riley lack. Jazmine, for her part, seems to return this affection and even seems to think of him as family to a degree. She does become justifiably angry with him when he gets her into trouble or convinces her to break the rules (...Or Die Trying), but seems quick to forgive him. It often seems that Robert treats Jazmine more like his grandchild than he does his own grandchildren. Although in Robert's dream about Stinkmeaner he threw her down the stairs with no regard and during the fried chicken flu he did not hesitate to reject her coming into the house.