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. He had a close relationship with his sister, Cookie Freeman, who was the smarter and more responsible of the siblings, and often referred to Robert as her "Favorite Dumbass." 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 in 1955 and likewise refused to give up his seat. The bus driver was only offended by Rosa's, not his, unwillingness to move, however; he also 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 accidentally got on the wrong bus with the Freedom Riders when he was trying to escape from a bus terminal employee for using the white's only bathroom. The aftermath of the horrifically dangerous ordeal saw Robert doing some jail time with the Freedom Riders leader, Sturdy Harris, who was of questionable sanity. He was obviously married at one point and had a son (Huey and Riley's dad). 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 his son and daughter-in-law 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. In 1980 he had a romance with a woman named Marietta, suggesting that his wife probably died in the 1970s or earlier (via Fandom).