Kenny 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.

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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.

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After 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.

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Cleveland 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.

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Cleveland uses Holt to cheat and get Stoolbend's high school baseball team to win state.

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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.

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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.

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Rallo befriends a Jewish man at the retirement home during the holidays, and Cleveland finally stands up to his father physically, but gives him a heart attack.

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Donna, frustrated by her husband's laziness on the weekends, nags Cleveland to help her around the house and to do something more with his life. To prove to Donna he can be as charitable as her, Cleveland recruits his buddies from Quahog and Stoolbend to participate in the First Annual Charity Beer Walk. When Donna gets injured at the event, Cleveland has to take over the housework.

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Cleveland 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.

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After 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.

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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.

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Cleveland 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.

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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.

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After 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.

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When Cleveland sees all of his childhood possessions around town, he learns that his parents, Freight Train and Cookie, have been selling his stuff to get money after being scammed out of their life savings. Together, Cleveland, Freight Train and their friends get together to bring down the con man who targeted their family. Meanwhile, Rallo gets a toy microphone and tries his hand at being a commentator, announcer and stand-up comic.

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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.

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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.

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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.

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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.

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When Rallo and his pals Bernard and Theodore perform in the school talent show, their rap about fiscal responsibility is not well-received by their classmates. Meanwhile, after Cleveland gets his own cable-access television show, the reviews are less than positive so he takes some tips from the most successful daytime talk shows that appeal to women.

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Cleveland creates his own comic book superhero and takes the entire family to a comic book convention in San Diego, where he discovers that Donna was once the star of a blaxploitation film.

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