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- Cleveland Brown moves back to his hometown in Virginia, where he finds his high school sweetheart and her two troublemaking kids.
- Adam Sullivan is a promising young A.U.S.A. whose intelligence is bound with a gullible nature that presents an uphill battle in his pursuit of both career and romantic success. At work he must argue cases against Susan Rakoff, a beautiful, savvy public defender who regards the A.U.S.A.s as enemies of the people. Adam is also challenged by his reluctant supervisor Geoffrey Laurence, and wide-eyed paralegal Wally, whose social ineptitude is matched only by his newfound devotion to Adam. Working alongside Adam as an Assistant U.S. Attorney is Ana Rivera, a former cop with the street experience to compensate for Adam's occasional naïveté. Also in Adam's life is his roommate Owen Harper, a trusted friend who reminds Adam of the lighter side of life outside the world of federal prosecution.
- After losing his house in a divorce settlement, Cleveland moves to Virginia and marries his high school sweetheart.
- 2009–201321mTV-146.1 (452)TV EpisodeCleveland blows his chance to escort his new stepdaughter to a dance when he accidentally runs over the family dog.
- Tim gets Cleveland a job as a cable telemarketer. But when Cleveland does a better job than him, Tim wishes bad things on Cleveland.
- Cleveland gets Lester's son Ernie to become Cleveland Jr's friend, but Ernie accidentally gets taken away by Child Services.
- Jr. announces his plans to stay a virgin until marriage, much to Cleveland's dismay.
- Cleveland celebrates his first Thanksgiving with his new family, including his own parents Cookie and Freight Train as well as Donna's Auntie Momma who all make a surprise visit to shake things up in Stoolbend. However, the holiday gets complicated when Roberta and Federline decide to celebrate on their own, and Cleveland discovers a surprising secret about Auntie Momma that changes his impression of her forever
- 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.
- Cleveland convinces Junior to play for the high school baseball team, but can't hide his embarrassment after he finds out that he is terrible.
- When Roberta's new teacher encourages Roberta to alter her appearance, Cleveland Jr. befriends the disguised Roberta and falls in love with her. Meanwhile, Cleveland comes up with an interesting new invention.
- Cleveland tries to help some troubled teens at the high school get on the right path, but doesn't realize that in the process he's become a drug dealer.
- After Cleveland accidentally discovers Holt's embarrassing secret, he sets Holt up on a date with a woman who turns out to be abusive. Meanwhile, Rallo waits for Cleveland Jr. to pass his pet fish.
- 2009–201330mTV-147.1 (331)TV EpisodeCleveland Jr. vows revenge on his father after he gets him a job at the Broken Stool but later conspires to get him fired.
- Cleveland and his friends prepare to enter Stoolbend's annual boat race as a team, but when Cleveland's celebrity idol moves to town, Cleveland makes it priority to befriend him. And when his new pal invites him to join his boating team, Cleveland is forced to make a difficult decision. Meanwhile, Roberta gets wrapped up in her dreams of being a superstar.
- 2009–201322mTV-146.5 (300)TV EpisodeCleveland takes Donna on a belated honeymoon to New York, but Cleveland spends more time with his friends than her. Meanwhile, the kids try to sell a pilot to MTV, and Coach McFall tries to "rekindle a romance" with Tyne Daly.
- Cleveland is hailed as a hero after he protects his wife from a robber at an ATM--even though that isn't exactly what really happened.