The Cleveland Show - Season 1

After having his house damaged by Peter once again, Cleveland Brown and Cleveland Jr decide to leave Quahog and head to California to pursue his dream of being a minor league scout for a professional baseball organization. While passing through his hometown of Stoolbend, Virginia he bumps into his old flame, Donna Tubbs. She invites him to stay at her house for a couple of days, where Donna relays to Cleveland how she needs a father figure around for her kids after splitting with her ex-husband, Robert. While at Donna's house, he is introduced to Rallo and Roberta, Donna's kids, and the neighbors, including the local redneck and the family of bears, which include father Tim, his wife, and son Raymond.

Cleveland tries to make inroads with his new stepdaughter Roberta by asking her to accompany him to the school's father/daughter dance. Last year Robert did not show up. The evening seems to be going smoothly until Cleveland runs over the family pet on his way to get an ice cream cake for celebration. Then his redneck neighbor Lester takes it and eats it. This kills his chances of being accepted by his new kids. Rallo and Cleveland look for meadowlark lemon and Cleveland dives in nasty places looking to keep the secret but Lester and the others tell him to be honest.

Cleveland notices his son, Cleveland Jr. has no friends, and sets out to find him a good friend. He finds out that Lester's son, Ernie, has no friends, which Cleveland realizes is a perfect opportunity to have his son make friends with another friendless child. It goes well, but things take a turn for the worse. Ernie leaves his family and joins the Brown family, much to their dismay. Ernie is unsanitary and disgusting, which pushes Donna to make Cleveland call child services and get Ernie back in his home.

Cleveland looks for a job, first trying to be a grizzled police officer two days from retirement and also as a singing salesman at the Stoolbend Flea Market. Tim helps him get a job at Waterman Cable as a phone solicitor. Cleveland runs into an old high-school friend, Terry Kimple who is working as a cable installer for Waterman. When they were in school, Terry took the rap when they were busted for drugs. When Cleveland excels as a salesman, causing business to dry up for Tim, Tim prays for bad things to happen to Cleveland. Meanwhile, Roberta and Rallo feel resentment towards Cleveland Jr. for stealing their mother's affections from them and try to make him look bad until they learn the true extent of his feelings towards his own mother.

While watching a baseball game at Stoolbend Stadium, Cleveland sees Roberta kissing with Federline Jones. Cleveland tries to talk to Roberta about maintaining her virginity but while she admits she has yet to do anything, makes it clear that it is none of his business. Following the advice of his friends, he takes the family to church to hear about maintaining purity. Cleveland Jr. gets carried away in the moment and pledges his purity to Cleveland's dismay.

Cleveland and Donna get together with the neighbors, but while Cleveland is enjoying himself, Donna is less than thrilled and gives Cleveland the cold shoulder. When invited to spend more times with the neighbors, Donna decided to sneak out and spend more time with her old friends at a single mothers gathering. Getting away from Cleveland helps spark the relationship. Cleveland finds out that she was not spending time with the other wives but gets distracted. While on a day out tubing down a river with the kids, Cleveland stumbles across Donna and her friends who are shocked to find out she is married.

Cleveland celebrates his first Thanksgiving with his new family. His parents, Cookie Brown and Levar 'Freight Train' Brown arrive for Thanksgiving. Cleveland's dismal relationship with his father nearly lands him in a fight with his own father, until Donna's Auntie Momma shows up. She starts making comments on how outrageous she is after farting. Freight Train gains an infatuation over Auntie Momma and decides to have sex with her after a game of football. However, when Cleveland was taking out the garbage, he saw Auntie Momma in the bathroom, with a penis. Despite that Freight Train had sex with Auntie Momma (who secretly is a man), he did not even know about it.

Rallo becomes upset because Cleveland has taken over the house. While telling his friends about his troubles he decides it has to be either him or Cleveland. He plots to come between his mother and Cleveland, temporarily driving Cleveland from the bedroom. When Donna tries to reason with him, Rallo escalates the conflict by breaking his own leg, sending Donna on a one-way guilt trip. Cleveland tries to talk with him and discovers just how far Rallo would go. When Rallo discovers how much his mother misses Cleveland he agrees to a truce.

Cleveland and the family go to pick out a Christmas tree at Lester's lot. Cleveland has his eye on a nice large tree but Rallo insists on a smaller tree. Cleveland finds out that Donna and the family have been lying to Rallo, telling him the reason Robert cannot come around during the holidays is that he is an FBI agent. When Cleveland fills in as Santa Claus at his office holiday party, he has one too many egg nogs and lets the truth slip about Rallo's father. Rallo fails to connect that it was Cleveland posing as Santa and takes out his hostility on the figure of Santa. With Rallo's admiration for his dad destroyed, Cleveland tries to reconnect father and son in an attempt to save Rallo's Christmas spirit.

After a nostalgic flashback to the glory days as his high school's baseball all-star, Cleveland visits his alma mater to find out there is no longer a team because he and his friends insulted Wally as a teen. Now Principal Wally gives Cleveland one week to raise money to re-build the stadium before the season begins. They raise the cash from a generous donation by Mr. Waterman and organize the team on time. Cleveland then steps in as head coach and dusts off his retired jersey in an attempt to convince Cleveland Jr. to play ball instead of joining the math club. Cleveland Jr. turns out to have no skills, even going as far as deliberately interfering with a play to save a ladybug.

While Ms. Eck, Roberta's new teacher, encourages her to change her appearance to learn an important lesson, Cleveland Jr. befriends the disguised Roberta only to fall in love with her afterwards.

Meanwhile, Cleveland receives help from the guys in order to invent the perfect infomercial product.

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.

Holt admits to Cleveland that he wishes he had a special someone in his life. Determined to help his lonely friend, Cleveland introduces Holt to Jill, a cat-loving redhead who ends up being more than a handful. Meanwhile, Cleveland Jr. and Rallo anticipate the "birth" of Rallo's pet fish.

Cleveland Jr. gets a job at the local newspaper, and begins to learn responsibility. When he starts making changes to the bar that Cleveland and his friends hang out, a good old fashioned father-son rivalry breaks out. Meanwhile, Roberta gains a rival, who just happens to be wealthy, so her and Rallo plot a surprise for this new friend.

Cleveland and Donna road trip to the Big Apple for an overdue honeymoon, and to Donna's dismay, Cleveland allows the Stoolbend gang to tag along to help Coach McFall rekindle a long lost romance. Although, when Tim finds himself in a compromising situation and Lester's language gets him into trouble, Cleveland is forced to choose between his wife and his friends.

When Cleveland and Donna are mugged at an ATM, Cleveland is accidentally wounded in the tussle.
By the time the story hits the local news, the attention goes to Cleveland's head, but Cleveland's version isn't the whole story.

Meanwhile, Roberta takes advantage of Rallo, who thinks that his sister is dying of a terrible disease.

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.

Rallo gives Cleveland Jr. tips on how to woo the girl of his dreams; Cleveland challenges her boyfriend to a rap battle.

Cleveland and Cleveland Jr. teach Donna and the kids their tradition of celebrating Black History Month. However, when Rallo learns about his heritage at school, he provokes Cleveland into a battle royale with neighbor, Lester.

After Cleveland gambles away Roberta's college fund, Kendra discovers that Cleveland was actually cheated out of his money and recruits Donna and Arianna for a mission.

Much to his dismay, Cleveland finds out that Cleveland Jr. will inherit all of his ex-wife's belongings and that his parents, Cookie and Freight Train, plan to remarry. To add insult to injury, Freight Train dumps Cleveland as his best man in favor of Donna's ex-husband, Robert. In the end, though, Cleveland steps in to save the day.