Roberta and Rallo have a surprise for Lacey, Roberta’s wealthy rival. Meanwhile, Cleveland Junior learns responsibility while working at The Stool, but when he starts making changes to the guys’ hangout, a feud erupts between father and son.

Cleveland and Donna get mugged at an ATM and Cleveland gets shot, and the media makes it seem as if he was a hero. Meanwhile, Roberta convinces Rallo that she might be dying of a terrible disease and makes him do her bidding.

After his confidence is shattered, Cleveland plans a family vacation to Africa.

When Rallo's teacher forces him to spend the weekend at a retirement home to get to know the senior citizens during the holidays, he meets Murray, who teaches him about Hanukkah. In an attempt to rekindle Murray's holiday spirit, Rallo helps him escape, but when his new friend's health begins to suffer, Rallo has to bring Murray back to the home. Meanwhile, Cleveland trains for a boxing match against his bully of a father, Freight Train, which ends with some bumps and bruises.

After Cleveland fights to save the town’s drive-in movie theater, his efforts to preserve the town’s history is noticed by the Stoolbend Preservation Society and he is invited to attend a private dinner party at the home of the great-great-grandson of the town’s founding father.

While at the event, Cleveland learns of the town’s legacy and decides to take back his beloved town.