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. Meanwhile, Rallo is shocked when he discovers Roberta's dirty little secret.
Quagmire from Quahog brings news of Loretta's death, meanwhile Donna puts Cleveland on a high-fiber diet. Rallo gives Cleveland Jr. 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 "Cleveland's Angels" mission. Much to his dismay, Cleveland finds out that Cleveland Jr. To add insult to injury, Freight Train dumps Cleveland as his best man in favor of Donna's ex-husband, Robert.
Instead of continuing on their family-heritage trip to Africa, Cleveland and the family end up turning their layover into a tropical vacation. Cleveland crushes Cleveland Jr. Meanwhile, Rallo goes against his mom's wishes and eats way more Halloween candy than his teeth can handle.
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. 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.
Meanwhile, Cleveland trains for a boxing match against his bully of a father, Freight Train, which ends with some bumps and bruises. When Donna gets injured at the event, Cleveland has to take over the housework. After Cleveland criticizes her parenting skills, Donna lets him deal with Roberta by himself; Cleveland lets Roberta throw a house party. 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. When Cleveland discovers he and his wife are not actually married, and his best friend Terry is gay and in a relationship, they all decide to go to Vermont for a double wedding; Cleveland Jr.
After Cleveland learns that his parents have been scammed out of their life savings, he plans to bring down the con man who targeted his mother.
Cleveland is reunited with an old classmate "Fatty Patty", who is now skinny and beautiful and still has a crush on Cleveland. Cleveland and his friends decide to enter the Stoolbend Floaterboat Race, but Cleveland later ditches them for another team. Meanwhile, Rallo becomes too sick to go to school. When Cleveland Jr. 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.
In an effort to bond with the guys, Cleveland takes them on a camping trip hosted by Ric Flair but Cleveland is upset when he finds out that his best friend Peter Griffin came to Stoolbend and did not call him to hang out. When a hurricane hits Stoolbend, the Brown-Tubbs family tries to salvage what's left of their blown-away vacation. Donna makes Cleveland and Rallo spend the night in a haunted house. Meanwhile Cleveland's new friend goes on a murderous rampage and Roberta is stuck in a love triangle between a vampire and a werewolf.
Cleveland is embarrassed when he learns that Cleveland Jr. When Donna joins a women's support group and starts to complain about how Cleveland treats her, Cleveland dresses up as a woman to infiltrate the group and show Donna how good her life really is.
When Murray gets a girlfriend named Hazel, Rallo discovers she is after Murray's money and tries to save him from making a costly mistake. Donna signs Cleveland up for the gym but instead of working out, he takes a lazy short-cut to achieve results. While staging their own live nativity scene, Cleveland tells his family his version of the greatest holiday-themed blockbuster movie ever told.
When Junior starts dating a very attractive young lady, Cleveland gets green with envy and suspicious of her motives. When things start to get too serious between the two young lovers, Cleveland suspects that the young woman is using Junior to get a green card.
After getting himself into several cultural misunderstandings with his new and popular Latina neighbor, Cleveland attempts to make amends by demonstrating his knowledge of Latino culture. But Cleveland gets into a bind when he offers to babysit Chonie's son and winds up losing him.
Meanwhile, Junior sets up his new wife Cecilia on a Valentine's Day date but his jealousy gets the best of him. Determined to claim the first place trophy at the annual "Dancing with the Stools" ballroom dance competition, Donna recruits Cleveland Jr. But their hopes of taking home the big prize miss a beat when Cleveland Jr.
Meanwhile, Roberta babysits Rallo for a week, and learns that domestic responsibilities are not as easy as they seem. Excited to spend quality father-stepson bonding time with Rallo, Cleveland takes Rallo to his very first magic show, where they get hired to be the opening act. Thanks to Rallo's sharp wit in the role of the puppet, Cleveland and Rallo's ventriloquist act becomes a hit.
As their act gets rave reviews by fans and ventriloquist critic Graham Kensington, Rallo grows tired of Cleveland taking all the credit for their success. Not one to be taken for a dummy, Rallo proves that he is the heart of their comedic act. When Donna has a midlife crisis, Cleveland must come up with a clever way to sneak off with his buddies on a hunting trip without her finding out.
But a hunting accident leaves Cleveland slightly deaf, and his scheme to agree to all of Donna's ideas backfires when she makes a drastic life change and decides to go back to school. Meanwhile, Junior is up for an easy reelection as Student Body President, until Roberta decides to run against him.
Cleveland relies on energy supplements to keep himself awake in order to work overtime and earn enough vacation time to go on 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.
Cleveland plays golf against his dad and Cleveland Jr. 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.
After Donna becomes jealous when Cleveland gets too close to a female coworker, 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. One of Rallo's pranks goes too far and gets Cleveland Jr. So Cleveland takes matters into his own hands, and threatens to send Rallo to juvenile detention.
It's Homecoming Weekend at Cleveland's alma mater, so he volunteers to accompany Roberta on a college visit as an excuse to relive his crazy college days.
But when Cleveland's fraternity chapter gives him a less-than-brotherly welcome, Roberta comes to the rescue and discovers a bright future in higher education. Meanwhile, Rallo helps Cleveland Jr. Devout church choir girl Vanessa catches Cleveland Jr. Vanessa's fellow choir member, Hunter, confronts him for going to church for the wrong reasons, but the tables turn when Vanessa winds up being a handful for the boys. Meanwhile, Donna's ex-boyfriend returns home from Iraq and discovers that she is married.
But when an unexpected event leads the real Dee Dee to find Cleveland, he stages one last effort to reunite Donna with her mother, and the unlikely meeting helps the two women forge a new mother-daughter bond.
Roberta gives Cleveland Jr. But when Daisy mistakes Cleveland Jr. Meanwhile, Donna dons a sexy Halloween costume that gets her in trouble with the cops, and Roberta and Cleveland Jr. Meanwhile, Cleveland tries to open an airport bar but ends up drunk and flying a stolen airplane. Cleveland and Junior embark on an elaborate mission to free all of the turkeys before Thanksgiving while Rallo and Donna build a float for Stoolbend's Thanksgiving Day parade. When Donna reveals that she wants another baby, Cleveland realizes that the vasectomy he has had must remain a secret from her.
When Donna finds out that Cleveland has been lying to her, she pretends that's she's pregnant to get back at him. Tim the Bear formerly voiced by Seth MacFarlane and currently voiced by Jess Harnell , is one of Cleveland and Donna's neighbors in Stoolbend who just happens to be a bear. He is thirty-five years old and lives with his wife, Arianna, and his son, Raymond.
He has deep religious convictions often attending Stoolbend Community Church and having his honeymoon in Israel. He works as a telemarketer at Waterman Cable.
He apparently smokes in secret, as he asks Cleveland not to tell his wife about it. He also has a very deep Eastern European accent, has trouble with American euphemisms, and has a tendency to stammer a lot. He finds it racist when someone screams because he is a bear. Additionally, he often accidentally slashes things with his claws, something he is quite ashamed of.
In "Brown History Month", Cleveland stated that Tim's father was a black bear and that his mother was a kangaroo, actually making him a hybrid between the species rather than a bear. Tim has often hinted at his attraction to Donna, similar to Quagmire's attraction to Lois on Family Guy.
Lester Krinklesac voiced by Kevin Michael Richardson , is one of Cleveland and Donna's neighbors in Stoolbend, Lester is a redneck with a large beer gut. He is 38 years old and he is apparently on friendly terms with his neighbor Donna, being at first concerned that Cleveland is stalking Donna but promptly apologizes to her when he realizes Cleveland was an invited guest.
He becomes Cleveland's drinking buddy at The Broken Stool conversing with Tim and Holt, Cleveland even helped Lester get his son back from a rather money obsessed foster family. He was thought to be a Neo-Confederate, but it was revealed that he has no clue about any of that when he proclaims that the Navy Jack adorning his house is a "Dukes of Hazzard flag".
In the Season 1 finale, it is revealed Lester has a sister who is a stripper. He also appears to be very good at making racing cars. Holt Richter voiced by Jason Sudeikis , is a year-old frat boy wannabe. Holt attempts to be a suave, pop-culture reference-dropping bro, but the effect is undercut by his short stature he is short enough to be mistaken for a child, as proven by Kendra occasionally referring to him as "the baby man" , as well as the fact that he still lives with his mother.
He enjoys Game Boy and Entourage, and is frequently seen playing or practicing golf. He drives a Chrysler Crossfire named Appolonia. Holt has a tattoo of Jeremy Piven on his chest. His occupation is personal trainer at a local gym. Green-Jarvus Ben-Ellis codename: Dr. Fist starting with "Skip Day. Fist was originally called Green-Jarvis Ben-Ellis based on BenJarvus Green-Ellis had a private practice until he was approached by members of the New York Mafia to save one of their fellow members from multiple stab injuries.
Then he was approached by the FBI to put anesthesia on the Mafia Don enough to put him in a coma so that he can go under Witness Protection. Cleveland learns this when they end up pursued by members of the New York Mafia.
He was later shot by Cleveland when the New York Mafia failed to do the job. Cleveland was able to save Dr. Fist's life by doing it Operation style. Three months later, Dr. Fist decides to stay in Stoolbend now that the New York Mafia thinks that he is dead. Since the events of that episode, Dr.
Fist has become the newfound, fifth member of Cleveland's friend circle at The Broken Stool and has appeared with the cast in all subsequent episodes, featuring the group. One was a knockoff of Bart Simpson, called "Brat Simpson". Later in the episode, Rallo also mentions putting an end to his rodeo career, while it was still good, just like The Simpsons. This is a joke on the fact that "ending the show while it was still good" was something The Simpsons obviously never did.
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