Season 1

Everyone’s favorite soft-spoken neighbor, Cleveland Brown, is on the move after he decides it’s time for him and Cleveland Jr. to leave Quahog and go west. On their way to California, the duo makes an pit stop in Cleveland’s hometown of Stoolbend, VA, where he reunites with his old high school crush, Donna Tubbs. Although she comes with baggage in the form of a rebellious teenage daughter and a sharp-tongued 5-year-old son, Cleveland is still in love with Donna and is determined to start a new life.

Cleveland tries to make inroads with Roberta by asking her to accompany him to the school's father/daughter dance. The evening seems to be going smoothly until Cleveland has a mishap with the family pet and kills his chances of being accepted by his new kids.

Afraid that Cleveland Jr. has no friends, Cleveland invites his neighbor's son, Ernie, to the house; when Ernie gets too attached to the family, Cleveland has trouble getting him to go home.

When Cleveland needs a new job, Tim hooks him up at Waterman Cable. However, when Cleveland becomes the top salesman, Tim is green with envy and wishes for bad things to happen to Cleveland. But when Cleveland comes up on some bad luck and misfortune, Tim has a change of heart.

When Cleveland has "the talk" with Roberta, it scares Cleveland Jr. into taking a vow of chastity, but his sworn celibacy may not be all he had hoped for when he overhears Cleveland making fun of him. Meanwhile, Rallo shows an interest in attending church.

Cleveland is upset when he finds out that Donna is still attending a single mothers' support group in order to have a good time. Meanwhile, Cleveland Jr. runs for student council president with Rallo as his adviser.