When Cleveland discovers that he and his wife are not married and that his best friend, Terry, is gay and in a relationship, they all decide to go to Vermont for a double wedding; Cleveland Jr. tries to get Rallo to break a nasty habit.
When Cleveland's efforts to save the town's drive-in movie theater are noticed by the Stoolbend Preservation Society, he is invited to a private dinner where he learns about the town's legacy.
Cleveland discovers his parents have been selling his belongings because they lost their life savings to a scam artist; Rallo gets a toy microphone.
Lester appears to take his own life after losing his life savings; Rallo opens his own barbershop.
Donna becomes extremely jealous when Cleveland is reunited with a former high school classmate who is now thin and beautiful.
Cleveland and his friends get ready to enter Stoolbend's annual boat race; Cleveland is thrilled when his celebrity idol moves to town.
Cleveland becomes jealous when Cleveland Jr. bonds with Donna's ex-husband, Robert.
Rallo and his friends Bernard (will.i.am) and Theodore (T-Pain) perform a rap at the school talent show that is not well-received; Cleveland gets a cable-access TV show.
Cleveland takes the family to a comic convention to try to sell his comic book; Donna learns a that a Blaxploitation film she starred in will be shown; Cleveland Jr. tries to bring to the convention back to its roots.