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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 (451)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.
- Cleveland is embarrassed when Cleveland Jr. publicly announces that he will remain a virgin, but Jr. changes his mind after seeing Cleveland's reaction.
- 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 (329)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 (299)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.
- Donna becomes angry when Cleveland experiences unexpected grief at his ex-wife Loretta's funeral.
- Cleveland and Lester are ordered by a judge to work together on a float for the Stoolbend Unity Parade after they get in a fight, while Rallo launches a plan to steal Lester's Confederate flag.
- After Cleveland loses Roberta's college fund to a crooked casino owner, he is forced to resort to extreme measures to get the money back.
- 2009–201322mTV-146.5 (289)TV EpisodeCleveland's parents announce they are getting married and moving to Stoolbend. Cleveland Jr., fresh off inheriting his mom's fortune, offers to pay for the wedding. But can Cleveland and Freight Train play nice and get through it?
- Rallo conspires to kick Cleveland out of his mom's bed so that he can have her all to herself, while Roberta blows off her job of keeping an eye on Cleveland Jr. while on a field trip to Washington D.C..
- 2009–201322mTV-146.4 (355)TV EpisodeCleveland gets drunk as a Santa Claus and shatters Rallo's Christmas by telling him that his biological father is a deadbeat.
- Cleveland begins pimping out Terry for bachelorette parties as a "cable guy," and Cleveland Jr. gets on the bad side of Stoolbend's top rapper when he takes an interest in his girlfriend.
- 2009–201321mTV-146.3 (286)TV EpisodeKenny West is a single dad and struggling rapper whom Cleveland takes under his wing in attempt to prove his own prowess after receiving some surprising news about his childhood basketball camp nemesis. Together, Cleveland and Kenny write, record and perform a new hit single, "Be-Cleve in Yourself." The track burns up the charts and ignites Kenny's new rap career, but leaves Cleveland behind in the dust.
- 2009–201322mTV-146.6 (259)TV EpisodeCleveland and Rallo share a bonding experience through "mutton bustin'," but Rallo soon runs away with his sheep when he learns about his sheep's ultimate fate.
- 2009–201322mTV-146.5 (275)TV EpisodeAfter Cleveland and Donna argue over their individual parenting skills, Donna leaves Cleveland for the weekend so that he can take care of Roberta by himself.
- Cleveland is upset when Tim gets a promotion over him at Waterman Cable, so he tries to sabotage him. Meanwhile, Rallo takes advantage of Cleveland Jr. when he realizes that he thinks that Rallo's turtle can talk.
- 2009–201322mTV-146.8 (256)TV EpisodeCleveland gets in trouble after heckling the players at the NBA All Star Game, and Rallo makes friends with adult little person, who doesn't realize that Rallo is 5.
- After discovering that he's not married to Donna because her divorce was never finalized, Cleveland goes out on the town and accidentally discovers that Terry is gay. Meanwhile, Cleveland Jr. tries to cure Rallo of a disgusting habit.
- 2009–201322mTV-146.4 (237)TV EpisodeAfter he is tricked into defending a statue honoring a slave owner, Cleveland vows to get revenge by changing history and winning a Civil War battle reenactment for the North.
- 2009–201322mTV-146.3 (229)TV EpisodeCleveland buys back all of his childhood possessions from his parents after they try to get money to provide for themselves. Cleveland soon discovers that his parents were scammed by a con-man. Cleveland makes his father do menial labor around the house. Cookie reveals to Cleveland that she was the one who got scammed by the con-man after he promised to make her famous. Rallo uses a portable microphone set to become an announcer and a stand-up comic. Cleveland, his father, and his friends dress up like women so they can confront the con-man. Freight Train soon beats up the con-man and Rallo comments on the fight. The con-man tries to make Rallo famous, but he ends up scamming them again. Cleveland, Freight Train, and Rallo head home and they are wearing barrels.
- When Lester invests in Cleveland's beer truck business and loses his life savings, he is so upset that he decides to take his own life - or does he? Meanwhile, Rallo is tired of getting his hair cut by his mom and opens his own barbershop in the kitchen.
- When Cleveland is reunited with his former high school classmate, "Fatty Patty," who is now skinny, beautiful and still has a crush on Cleveland, Donna becomes extremely jealous and wary of Patty's motives for wanting to be friends with Cleveland. Patty turns out to be a little crazy, and after she tries to steal Cleveland's "essence," Donna goes on the hunt to stop her.
- In an animation first, the episode offers the audience a behind-the-scenes look at the "filming" of the episode. When Cleveland and Donna attempt to celebrate their anniversary, their unruly kids and disruptive friends, including Donna's ex-husband, Robert, get in their way.
- When Cleveland Jr. bonds with Donna's ex-husband, Robert, Cleveland becomes jealous that Jr. thinks Robert is so much cooler than him. In order to prove how cool he is to his son, Cleveland challenges Robert to a "Coolympics" competition.
- A hurricane cancels the Browns' cruise plans and leaves them at home without food. During the ordeal, Cleveland Jr. also declares that he does not believe in God.
- 2009–201322mTV-146.3 (257)TV EpisodeAfter his confidence is shattered, Cleveland vows to find his mojo again, and decides that a family vacation to Africa will do the trick. While on a layover in Hawaii en route, Cleveland gets derailed by mai tais, the ocean and plenty of sunshine, and realizes a few days in paradise is actually what he needs.
- 2009–201322mTV-146.5 (285)TV EpisodeCleveland crushes Cleveland Jr.'s spirit when he forbids him from trick-or-treating because he thinks he is too old. Junior reinvents himself as a "cool kid" and is invited to attend a Halloween party with Roberta. When Junior gets picked on and is unhappy with his new persona, Cleveland and the gang come to his rescue and encourage his enthusiasm for the holiday.
- Cleveland uses Holt to cheat and get Stoolbend's high school baseball team to win state.
- Cleveland Jr. and Kendra fight discrimination against fat people, and Rallo nearly drowns in the new pool while Cleveland is supposed to be watching him.
- Donna's sister Janet comes to town for Thanksgiving, hooks up with Holt, and then runs off to Las Vegas with him and leaves her two children behind in Stoolbend.