The Cleveland Show is a half-hour animated series that follows everyone's favorite soft-spoken neighbor Cleveland Brown to his hometown in Virginia, as he settles down with his high school sweetheart, her unruly kids and his 14-year-old-son, Cleveland Jr. Once in Virginia, Cleveland is welcomed by a collection of neighbors that includes a loudmouth redneck, Lester; a hipster wanna-be, Holt; and a family of talking bears. The Cleveland Show is a spinoff of the hit TV series, Family Guy.
Everyone's favorite soft-spoken neighbor, Cleveland Brown, is on the move after he decides it's time for him and Cleveland Jr. to leave Quahog and go west. On their way to California, the duo makes a pit stop in Cleveland's hometown of Stoolbend, VA, where he reunites with his old high school crush, Donna Tubbs. Although she comes with baggage in the form of a rebellious teenage daughter and a sharp-tongued 5-year-old son, Cleveland is still in love with Donna and is determined to start a new life.
Cleveland tries to make inroads with his new stepdaughter Roberta by asking her to accompany him to the school's father/daughter dance. The evening seems to be going smoothly until Cleveland has a mishap with the family pet and kills his chances of being accepted by his new kids.
Cleveland is concerned that Cleveland Jr. has no friends, so he invites his neighbor Lester's son Ernie (guest voice Howerton) to their house. A neglected Ernie becomes too attached to the family, leaving Cleveland to call child services to have Ernie taken back home. When the plan backfires, Cleveland helps Lester get his son back.
When Cleveland needs a new job, Tim hooks him up at Waterman Cable. However, when Cleveland becomes the top salesman, Tim is green with envy and wishes for bad things to happen to Cleveland. But when Cleveland comes up on some bad luck and misfortune, Tim has a change of heart.
When Cleveland has "the talk" with Roberta, it scares Cleveland Jr. into taking a vow of chastity, but his sworn celibacy may not be all he had hoped for when he overhears Cleveland making fun of him. Meanwhile, Rollo shows an interest in attending church.
Cleveland is upset when he finds out that Donna is still attending a single mothers' support group in order to have a good time. Meanwhile, Cleveland Jr. runs for student council president with Rallo as his adviser.
Cleveland celebrates his first Thanksgiving with his new family, including his own parents Cookie and Freight Train as well as Donna's Auntie Momma who all make a surprise visit to shake things up in Stoolbend. However, the holiday gets complicated when Roberta and Federline decide to celebrate on their own, and Cleveland discovers a surprising secret about Auntie Momma that changes his impression of her forever.
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.
When Cleveland fills in as Santa Claus at his office holiday party, he has one too many eggnogs and lets the truth slip about Rallo's father. With Rallo's admiration for his dad destroyed, Cleveland tries to reconnect father and son in an attempt to save Rallo's Christmas spirit. Meanwhile, Roberta becomes an animal rights activist and tries to save a reindeer.
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's no longer a team. Principal Wally gives Cleveland one week to raise money to re-build the stadium before the season begins. 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.
Roberta’s new teacher, Ms. Eck (guest voice Jane Lynch), encourages Roberta to alter her appearance to teach her an important lesson. Cleveland Jr. befriends the disguised Roberta only to fall in love with her. Meanwhile, Cleveland and the guys set out to invent the next infomercial product.
Cleveland (Mike Henry) comes to the rescue of frustrated parents by taking a group of delinquent teens under his wing. With the help of Cleveland Jr. (Kevin Michael Richardson), 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 (guest voice Fergie), 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 teaches Junior responsibility by challenging him to get a job, and to his own delight, Cleveland Jr. lands a job working at The Stool. However, when Cleveland Jr. starts commenting on the number of beers his father consumes and sets limits on the guys' time at the bar, a feud erupts between father and son. Meanwhile, Roberta competes with Lacey, the rich girl in school, and gets more than she bargained for.
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.
While using an ATM, Cleveland and Donna are mugged and Cleveland gets wounded. Meanwhile, Rollo thinks Roberta is dying of an illness and she decides to use her "illness" to take advantage of Rallo.
Cleveland changes his diet.
Acting as his brother’s wingman, Rallo (Mike Henry) gives Cleveland Jr. (Kevin Michael Richardson) a few pointers on how to win over the girl of his dreams, Chanel (guest voice Henson). When Cleveland Jr. finds out Chanel’s boyfriend is local rap star Kenny West (guest voice Kanye West), he challenges Kenny to an epic Stoolbend rap battle to compete for Chanel’s heart.
Cleveland (Mike Henry) and Cleveland Jr. (Kevin Michael Richardson) teach Donna (Sanaa Lathan) and the kids their tradition of celebrating Black History Month. However, when Rallo (Mike Henry) learns about his heritage at school, he provokes Cleveland into a battle royale with his neighbor.
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 an undercover 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 (guest voice Francis Callier) and Freight Train (guest voice Craig Robinson), plan to remarry. To add insult to injury, Freight Train dumps Cleveland as his best man in favor of Donna's ex-husband, Robert (guest voice Corey Holcomb). In the end, though, Cleveland steps in to save the day.