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Hillary (AKA "Big Skeez") is a member of the Crazy Eights and a drug-dealing juvenile delinquent teen mom with a history of abandoning her many babies.
She is voiced by Ari Graynor.
In "Our Gang", Big Skeez was causing trouble at Stoolbend High School, where she was seen occupying the men's bathroom, giving birth to a baby in there, which she later got rid of. Despite, of course, being disgusted by this complete depravity, Cleveland congratulated her on her mothership. After the antics of the troubled teens led to Principal Farquhare getting trampled, he called them into the gym for a PTA meeting the next day, over the phone, as he was in the hospital and Big Skeez was there. Cleveland coached the troubled teens on their bad behavior and said that he used to be a thug just like them. Big Skeez questioned what had things he did and Cleveland, put on the spot, lied, saying that he shot a kid, (he was just quoting the character Al Powell from the movie Die Hard). When saving Junior's life, Big Skeez bribed Momstabba with a condom full of pills that she swallowed the day before and had recently shat out. She gracefully gave the Stoolbloods a condom full of used drugs and said that she was granting him the drugs with love. After the ordeal was over, Big Skeez said that she was giving up her life of crime and promised to keep her next baby.