The Cleveland Show is a spin-off of the much-loved series Family Guy. The series features the adventures of Peter Griffin neighbor Cleveland Brown. He moves to his hometown in Virginia with his 14-year old son, Cleveland Jr. Many years ago, Cleveland was a high school student madly in love with a beautiful girl named Donna. Much to his dismay, his love went unrequited, and Donna wound up marrying another man. Cleveland once told Donna he would always love her, and if this man ever done her wrong, he'd be there when she called. Well, this man done her wrong. Donna's husband ran off, leaving Donna with a teenaged daughter and young son. Now she's open to Cleveland and offered him another chance at love. Unattached after the Loretta-Quagmire debacle and true to his word, Cleveland joyously unites with Donna, and he and his son move to Virginia to join their new family.
After Donna becomes jealous when Cleveland gets too close to a female co-worker, a music video made from footage of his workplace shenanigans goes viral and attracts the attention of a big-time music producer. He's attracted to Donna as well, making Cleveland jealous.
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.
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 relies on energy supplements to keep himself awake in order to work overtime and earn enough vacation time to go to 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.
A hunting accident leaves Cleveland partially deaf, so he decides to simply agree with all of Donna's ideas. And Donna, who's having a midlife crisis, decides to go back to school. Meanwhile, Roberta runs against Cleveland Jr. for student-body president.