Cleveland Orenthal Brown Sr. is a recurring character in Family Guy and the main character/protagonist of The Cleveland Show. While originally not a villainous character during his existence on Family Guy, upon starring in The Cleveland Show the character became far more cynical and gained several villainous and jerk-like traits, becoming a full-blow villainous protagonist with little to no morals.
Until recently he was married to Loretta Brown, but they separated after Loretta had an affair with Quagmire, although they still have feelings for each other. Together they had a son, Cleveland Brown Jr. Eventually, Loretta gains his house and Cleveland has to move. Cleveland is now married to Donna Tubbs and has two stepchildren, Roberta and Rallo. He also sports a mustache and often offers deep insight that the other characters are unable to see.
Cleveland grew up in Stoolbend and played baseball at high school, where he hung out with Terry and Gordy. He was in love with Donna, but Donna was dating Robert at the time. At some point before 1984, he moved to Quahog (although this is contradicted in Field of Streams when he is shown at Stoolbend High). Here he met Peter Griffin, Glenn Quagmire, and, years later, Joe Swanson, who he became friends with. The foursome became drinking buddies, and are close friends.
He used to be an accomplished auctioneer, but was struck in the head by a totem pole, which resulted in his speech being permanently slowed. Cleveland was also the president of the Quahog Chamber of Commerce. When he was in Quahog, he was the proprietor of Cleveland's Deli. However, moving to Stoolbend led to him needing a new job; in Birth of a Salesman, Tim was able to get him a job as a telemarketer at Waterman Cable, where he was later promoted to cable installer. He has also dabbled in other jobs, being a police officer and an actor (apparently being the "black guy in Die Hard").
Cleveland lost his virginity when he was nine, and may have been married before he met Loretta, suggested in a scene from the Family Guy episode Death Lives, when Cleveland meets Peter in the 80's. Cleveland picks up Peter in his van, and Peter asks to go to Rhode Island, then checks if it's okay with Cleveland. Cleveland then mentions something to the effect of being away from "Maxine, the Cheatin' Queen". Maxine may or may not have been Cleveland's first wife. As Maxine has not been shown on screen, it is largely accepted as Family Guy canon that Loretta was Cleveland's first wife.
Cleveland and Loretta were married soon after Cleveland moved to Quahog, after which they had Cleveland Jr.. Although at first it appears that Cleveland and Loretta had a decent marriage for a time, the relationship soon soured due to Loretta's feeling that Cleveland was incapable of being anything other than lethargic and laid-back. As a result Loretta persuade a brief affair with Glenn Quagmire, partly in an effort to hurt Cleveland. The two then separated with Cleveland getting custody of Cleveland Jr. For a while following his divorce he dated a woman named Bernice (also voiced by Alex Borstein), who had a higher voice than Loretta's, but seemed as equally bossy. Presumably his desire for a more feminine, traditional woman caused him to break up with Bernice and marry Donna, as that is the woman Cleveland ultimately sought. While he originally did not take Donna on a honeymoon, he eventually brought her to New York City a few months after they wed to properly celebrate.
He now stars in a spin-off of Family Guy, entitled The Cleveland Show!, which premiered on September 27, 2009. Cleveland officially left Family Guy when The Cleveland Show! started (though he still made occasional guest appearances). His son, Cleveland Jr. has also left the show and has gained weight, as well as now suffering from astigmatism (In the show's fourth and final season it is revealed that the new Cleveland Jr. is a secret agent that killed the Cleveland Jr. from Family Guy and took his place). Cleveland's new house, located in Stoolbend, Virginia, is surrounded by a variety of neighbors, just like in Family Guy.
During the show's second season, Cleveland went through a mid-life crisis after realizing how much more Barack Obama had done with his life than Cleveland had. To rectify this, Cleveland helped out Kenny West and his daughter, Candice. Eventually, he wrote and sang a rap with the young Kenny, Be Cleve In Yourself, and served as his manager for a short while before he was fired.
Following the cancellation of The Cleveland Show!, Cleveland officially returned to Family Guy and he and his new family moved back into Cleveland's old house.
Due to his relaxed nature, the thought of Cleveland performing villainous deeds seemed unthinkable (at least in Family Guy), however since his personality change in the Cleveland Show he has performed many villainous actions:
- In Family Guy, Cleveland was nearly close to beating Quagmire to death with a bat for the affair with his wife, but he snapped out of it knowing that Quagmire was his friend. Cleveland initially did not do anything about the affair, until Peter unintentionally persuaded him to take vengeance against Quagmire.
- In The Cleveland Show, after Rallo almost drowns and blackmails Cleveland for it, Cleveland dunks Rallo's head in the pool twice just so Rallo would stop bossing him around, although this could be a sense of cruel and unusual punishment since Cleveland was asserting himself.
- In Field of Streams, it is revealed through a flashback that Cleveland, along with Terry, was a high school bully to Principal Wally Farquhare, whom he chased down and intended to beat up when he threatened to turn them in for drinking beer on campus, but backed off when he saw him wet his pants out of fear of Cleveland. History later repeats itself in the present after Farquhare angers Cleveland by trying to humiliate Junior at a baseball game. (Interestingly, his history as a bully makes it bewildering to some fans that he can easily be pushed around and even bullied himself in the present.)
- In "The One About Friends", Cleveland murders Ernie's foster parents and several others with Cletus in a blaze of gunfire.
- During a basketball game in his backyard, he mercilessly and painfully knocks out Rallo and his friends in order to win the game and only cheers with his wife upon his victory despite the kids' state of pain.
- Cleveland cheats on Loretta with some prostitutes on few occasions.
- During one episode, he, like his stepson, Rallo, experienced racism towards white people, and it all began with the rivalry that they had temporarily with Lester.
- During the Christmas episode, he psychologically abused Rallo, telling him that his father was a hebrio and was not "anyone" in life.
- In the episode "Our Gang", Cleveland is in the business of cocaine trafficking. This activity led him and his son to almost die at the hands of a rival gang.