Cleveland takes a struggling rapper (Kanye West) under his wing and, together, they write and record a new hit single.

Cleveland and Donna try to celebrate their anniversary, but their kids, disruptive friends and Donna's ex-husband get in the way.

After his confidence is shattered, Cleveland plans a family vacation to Africa.

Cleveland Jr. cannot go trick-or-treating on Halloween because his father thinks he is too old; when Junior reinvents himself as a "cool kid," he gets picked on and becomes unhappy with his new persona.

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.

The Brown family spends Thanksgiving in Las Vegas.

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. In an attempt to rekindle Murray's holiday spirit, Rallo helps him escape, but when his new friend's health begins to suffer, Rallo has to bring Murray back to the home. Meanwhile, Cleveland trains for a boxing match against his bully of a father, Freight Train, which ends with some bumps and 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.

Tim becomes consumed with power after accepting a management position at Waterman Cable; Rallo uses the class pet turtle to play tricks on Cleveland.

Cleveland and Donna celebrate Valentine’s Day with a trip to Los Angeles after scoring courtside seats to the all-star basketball game. Caught up in the excitement, Cleveland gets rowdy and talks smack to the players from the sideline throughout the game. The basketball champs, feeling hurt, seek revenge by paying a surprise visit to Stoolbend and putting Cleveland in his place.

Cleveland discovers a shocking secret about his wife & his best friend Terry.

Meanwhile, Cleveland Jr. tries to get Rallo to break a nasty habit.

After Cleveland fights to save the town’s drive-in movie theater, his efforts to preserve the town’s history is noticed by the Stoolbend Preservation Society and he is invited to attend a private dinner party at the home of the great-great-grandson of the town’s founding father. While at the event, Cleveland learns of the town’s legacy and decides to take back his beloved town.

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 Mr. Microphone and tries his hand at being a commentator, announcer and stand-up comic

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.

Meanwhile, 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.