Cleveland and Donna are excited to have the house to themselves when Cleveland Jr. and Roberta go on a school trip to Washington, D.C., but a disgruntled Rallo will do whatever it takes to keep Cleveland and Donna apart. Meanwhile Roberta's partying gets out of control and Cleveland Jr. comes to her rescue.
Coach Cleveland comes to the rescue of frustrated parents by taking a group of delinquent teens under his wing. With the help of Cleveland Jr., he creates a new club dubbed "The Crazy Eights," and hopes that it will keep the kids on the straight and narrow. However, he is soon mixed up in bad business, and only the "Crazy Eights" can help him out.
When Cleveland is diagnosed with high cholesterol, Donna puts him on a new high-fiber diet, which causes an intestinal backlash. It may stink up the place, but Cleveland quickly realizes his gas might score him a few points in the Broken Stool's karaoke contest. Meanwhile, Quagmire pays a visit to Stoolbend to deliver Cleveland some upsetting news.
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.
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.
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.
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 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 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.
Cleveland's upset when Peter Griffin visits Stoolbend and doesn't look him up, so he decides to bond with other friends on a camping trip hosted by wrestler Ric Flair. It turns rowdy. Meanwhile, Donna wants to show that Rallo is as smart as the other kids in his class, so she forces him to enter a Quiz Bowl tournament.
When a hurricane hits Stoolbend, the Brown-Tubbs family tries to salvage what's left of their blown-away vacation. Meanwhile, Cleveland Jr. makes a surprising religious declaration. Part 1 of the three-part crossover "Night of the Hurricane" with Family Guy (10x02 = Pt.2) and American Dad! (8x02 = Pt.3).
When Rallo’s elderly best friend Murray gets a new girlfriend named Hazel (guest voice Kathryn Joosten), Rallo realizes that Hazel is after Murray’s money and tries to save him from making a costly mistake. Meanwhile, Donna tells Cleveland that he’s too fat and needs to lose weight, so she signs him up for the gym. But instead of working out, Cleveland takes a lazy short-cut to achieve results
To help pass time while posing in a holiday nativity scene, Cleveland tells his family his own version of one of his favorite holiday stories, “Die Hard”. In Cleveland’s version, when Waterman Cable Company is taken hostage on Christmas Eve by a group of terrorists, including Tim the Bear, Lester, Federline & Kendra, a barefoot Cleveland – wearing a tank-top much like the one Bruce Willis wore in the movie – must endure window-shattering shoot-outs and fist fights with his friends to save his wig-wearing wife, Donna, in a parody of the greatest holiday-themed blockbuster movie ever told.
Determined to claim the first place trophy at the annual "Dancing with the Stools" ballroom dance competition, Donna recruits Cleveland Jr. to be her partner. But their hopes of taking home the big prize miss a beat when Cleveland Jr. professes his love for Donna – just moments before their well-rehearsed routine. Meanwhile, Roberta babysits Rallo for a week, and learns that domestic responsibilities are not as easy as they seem.
Excited to spend quality father-stepson bonding time with Rallo, Cleveland takes Rallo to his very first magic show, where they get hired to be the opening act. Thanks to Rallo’s sharp wit in the role of the puppet, Cleveland and Rallo’s ventriloquist act becomes a hit. As their act gets rave reviews by fans and ventriloquist critic Graham Kensington (guest voice Bryan Cranston), Rallo grows tired of Cleveland taking all the credit for their success. Not one to be taken for a dummy, Rallo proves that he is the heart of their comedic act.
When Donna has a midlife crisis, Cleveland must come up with a clever way to sneak off with his buddies on a hunting trip without her finding out. But a hunting accident leaves Cleveland slightly deaf, and his scheme to agree to all of Donna’s ideas backfires when she makes a drastic life change and decides to go back to school.
Cleveland relies on energy supplements to keep himself awake in order to work overtime and earn enough vacation time to go on a Spring Break cruise with his family. But when his energy pill addiction forces him into rehab and his desperate attempt to escape to the cruise liner goes wrong, he finds himself held hostage by pirates threatening the safety of those aboard the ship, including his own family.
Rallo's viewing of Tim Gunn's reality show is interrupted when Cleveland decides to watch the college basketball tournament with Freight Train, but he quickly becomes frustrated when Freight Train enjoys spending quality bonding time with Cleveland Jr. instead. Once Cleveland learns the real reason behind Freight Train's cold attitude, he is determined to find a new father figure and goes head-to-head against his dad and Cleveland Jr. in the two-man golf tournament. Meanwhile, Rallo purchases a fancy sports car, but his speedy ride with his buddies takes a dangerous drive off-course.
Cleveland is labeled "The Whitest Man in America" after he wins a dance competition for the chance to attend a pop sensation's concert. Unable to shake off his new reputation, Cleveland is determined to understand his roots and where he came from. Everything starts to make sense when he is reunited with his former nanny Barbara, a high class woman with a taste for refined culture. But even though Cleveland's nanny influenced many of his interests growing up, Cleveland finally learns that happiness comes from being comfortable in your own skin.
Cleveland Brown moves with Cleveland, Jr. from Quahog, Rhode Island to his hometown of Stoolbend, Virginia to reunite with his high school girlfriend. This version has different dialogue from the version which finally aired on 27th September 2009.