Cleveland Brown and Cleveland Jr. leave Quahog and take to the road. On their way to California, they stop in Cleveland's hometown of Stoolbend, VA, where he reunites with his old high school crush, Donna Tubbs. Cleveland, still in love with Donna, is determined to start a new life with her, even if Donna's kids aren't exactly angels.moreless
Cleveland, wanting to make his new stepdaughter like him more, asks her to accompany him to the school's father/daughter dance. All goes well until Cleveland has a mishap with the family pet and ruins his chance.
When Cleveland Jr. and Roberta go on a school trip, Cleveland and Donna are excited to have the house to themselves. However, Rallo tries his best to keep Cleveland and Donna apart. Meanwhile Roberta's partying gets out of control and Cleveland Jr. comes to her rescue.
After having too much egg nog at the office party, Cleveland spills the beans about Rallo's father. Cleveland tries to reconnect father and son in an attempt to save Rallo's Christmas spirit. Meanwhile, Roberta becomes an animal rights activist and tries to save a reindeer.
Cleveland visits his old high school to find out there's no longer a baseball team team. Given one week, Cleveland attempts to raise money to re-build the stadium before the season begins. In an effort to get Cleveland Jr. to play baseball instead of joining the math club, Cleveland becomes head coach of the team.moreless
Cleveland takes a group of delinquent teens under his wing, to the thanks of their frustrated parents. He and Cleveland Jr. create a new club to try and keep the kids on the straight and narrow. However, things don't turn out so well.
Holt admits to Cleveland that he wishes he had a special someone in his life. Cleveland, determined to help his friend, introduces him to a cat-loving redhead who ends up being more than Holt can handle. Meanwhile, Cleveland Jr. and Rallo anticipate the "birth" of Rallo's pet fish.
Cleveland Jr. gets a job at the The Broken Stool, and begins to learn responsibility. When he starts making changes to the bar that Cleveland and his friends hang out, a good old fashioned father-son rivalry breaks out. Meanwhile, Roberta gains a rival, who just happens to be wealthy, so her and Rallo plot a surprise for this new "friend."moreless
Cleveland and Donna road trip to the Big Apple for an overdue honeymoon, and to Donna's dismay, Cleveland allows the Stoolbend gang to tag along to help Coach McFall rekindle a long lost romance. Although, when Tim finds himself in a compromising situation and Lester's language gets him into trouble, Cleveland is forced to choose between his wife and his friends.moreless
Tim, Arianna, Lester, Kendra, Donna and Cleveland participate in a karaoke contest at the Broken Stool. However, Cleveland's gas problems end up humiliating Donna. And an untimely death leaves Cleveland in emotional turmoil.
Cleveland and Cleveland Jr. teach Donna and the kids their tradition of celebrating Black History Month. However, when Rallo learns about his heritage at school, he provokes Cleveland into a battle royale with neighbor, Lester.
Much to his dismay, Cleveland finds out that Cleveland Jr. will inherit all of his ex-wife's belongings and that his parents, Cookie and Freight Train, plan to remarry. To add insult to injury, Freight Train dumps Cleveland as his best man in favor of Donna's ex-husband, Robert. In the end, though, Cleveland steps in to save the day.moreless
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