When Cleveland destroys Rallo and his friends during their basketball game, he reminisces about his childhood playing days including beating a kid named Barry Obama whom Donna informs him is now President Obama.

Cleveland tells the boys they are staying with Robert Tubbs so that Cleveland and Donna can celebrate their anniversary. Roberta announces she is going to a friends house and an unseen stagehand yells that Cleveland is fat.

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.

Cleveland Jr. tries to become a "cool kid" and attend a Halloween party, when he is told he is too old to trick-or-treat. Meanwhile Rallo eats too much candy.

Coach Cleveland gets greedy to win the high school baseball state championship game and turns to cheating when his star pitcher goes out for the season.

Cleveland Jr. and Kendra, ashamed of their appearance in a swimsuit, feel left out of the fun when the family spends an afternoon in the pool and petition to pass a bill to grant equal rights for those who are overweight. Disgruntled by their defeat in the polls, Junior and Kendra flee to Wisconsin, a land where they feel more free and accepted, and Cleveland and Lester vow to bring them back to where they belong.

Donna's show-off and bossy sister, Janet, and her unruly children come to town to celebrate Thanksgiving with the Browns. Cleveland, still bruised by their past, wants nothing to do with her this Thanksgiving and attempts to drive her out. However, his plan backfires when Janet and Holt fall in love and run away to Las Vegas to elope, saddling Cleveland and Donna with the responsibility of Janet's kids.

When Rallo's teacher forces him to spend the weekend at a retirement home to get to know the senior citizens during the holidays, he meets Murray, who teaches him about Hanukkah. Meanwhile, Cleveland trains for a boxing match against his bully of a father, Freight Train, which ends with some bruises.

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.

At Donna's suggestion, Cleveland and Rallo start spending more time together; Cleveland Jr. becomes jealous of Rallo and Cleveland's new relationship.

After Cleveland criticizes her parenting skills, Donna lets him deal with Roberta by himself; Cleveland lets Roberta throw a house party.

When a management position opens up at Waterman Cable, Cleveland and Terry are surprised when Tim gets the job. At first Cleveland thinks it will be great to have his friend as his boss, but when Tim goes on a power trip and schedules a company retreat during Cleveland's Super Bowl party, Cleveland must take matters into his own hands to put a stop to Tim's tyrannical ways.

Cleveland and Donna win tickets to the 2011 NBA All-Star Game. Meanwhile, Rallo ends up befriending a midget named Marty Barty.

When Cleveland discovers Donna has Roberta pour out his special coffee, hurt and mad. He demands to know what else she has been hiding from him. She reveals that she never finalized the divorce with Robert.

After attempting to take the family out for a drive-in movie, Cleveland discovers the drive-in is set to be demolished. Cleveland fights to save the town's drive-in movie theater, winning over the town council with a song.

After Cleveland learns that his friends own his old stuff, he confronts his father who is selling his childhood items. Cleveland buys his stuff back but Donna tells Cleveland that there is no room for the items. So he puts it all in a storage area were he finds out his parents are now living.

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.

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.

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.

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.

Cleveland takes the entire family to a comic convention in an attempt to sell his comic book, "Waderman." While there, Donna is horrified to find out that Robert Rodriguez is screening a Blaxploitation film that she starred in when she was younger, and Cleveland Jr., tired of Comic-Con being a playground for Hollywood to peddle their projects, gathers a band of geeks together to take the Con back to its true origins.