Harder, Better, Faster, Browner 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.
Cleveland Live! 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.
How Cleveland Got His Groove Back 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.
It's The Great Pancake, Cleveland Brown 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 he gets picked on and is unhappy with his new persona, Cleveland and the gang come to Junior's rescue and encourage his enthusiasm for the holiday.
Little Man On Campus 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.
Fat And Wet 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.
Another Bad Thanksgiving 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. Donna, Cleveland and the kids immediately head to Vegas to confront Janet and save their family Thanksgiving. While in Vegas, Rallo and Cleveland Jr. stumble upon a winning slot machine and find a woman of age to cash it in for them in exchange for an "escort" to dinner.
Murray Christmas 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.
Beer Walk! 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.
Ain't Nothin' But Mutton Bustin' When Cleveland and Rallo take Donna's advice and spend some more time together, they discover Rallo's talent for a rodeo-like sheep-riding sport called "mutton bustin'." But when Donna discovers how dangerous their new hobby can be, she orders them to stop, forcing Cleveland and Rallo to sneak around behind her back. Meanwhile, Cleveland Jr. gets jealous of Rallo and Cleveland's new relationship and tries to sabotage their time together.
How Do You Solve A Problem Like Roberta? After Roberta stands Donna up at the school carnival, Donna is hurt when she realizes how much they have grown apart. Donna tries to explain to Cleveland how she feels for support, but Cleveland instead criticizes her parenting skills. Cleveland seems to think he's such a good parent, so Donna decides to let him test his parenting skills on a teenage girl and leaves him to deal with Roberta by himself. In an attempt to win Roberta's approval, Cleveland lets her throw a house party, which ends up causing her to run off with her new boyfriend, Diego, and leading Cleveland, Federline and Raymond on a wild goose chase to save her.
Like A Boss 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. Meanwhile, it's Rallo's turn to take the class pet turtle home from school, and he soon realizes that he can use the pet to play tricks on Cleveland Jr.
A Short Story And A Tall Tale 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. Meanwhile, Rallo befriends a little person at the grocery store who he mistakes for a child and gets into some adult trouble when he leaves his new friend's sister at the altar.
Terry Unmarried Cleveland makes two huge discoveries in his personal life. First, he finds out that Donna never legally divorced her ex-husband, so she and Cleveland are not legally married. Then, he discovers that his best friend Terry is gay and has been dating a guy named Paul. In light of these new developments, Cleveland, Donna, Terry and Paul decide to go to Vermont and have a double wedding ceremony. Meanwhile, Cleveland Jr. tries to help Rallo break a nasty habit.
The Blue, The Gray And The Brown 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.
The Way The Cookie Crumbles 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.
To Live And Die In VA 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.
The Essence Of Cleveland 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.
Ship'rect 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.
Back To Cool 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.
Your Show Of Shows 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.
Hot Cocoa Bang Bang 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.