When Lester invests in Cleveland's beer truck business and loses his life savings, he is so upset that he decides to take his own life, or does he? Meanwhile, Rallo is tired of getting his hair cut by his mom and opens his own barbershop in the kitchen.
Cleveland and Donna score tickets to an all-star basketball game in Los Angles, but they soon get into trouble when Cleveland gets drunk and insults the players, who decide to teach him a lesson in manners.
Tim gets promoted at work after a co-worker dies and he lets it all go to his head. Meanwhile, Rallo plays a trick on Cleveland Jr. by making it look like his class turtle can talk.
Donna is hurt when she realizes how much her and Roberta have grown apart. She goes to talk to Cleveland about it who ends up criticizing her parenting skills. Donna wants to test Cleveland, proving that parenting a teenage girl is difficult. She leaves Cleveland to take care of Roberta for a night. He ends up having a party to gain her approval, but Roberta ends up running off with her boyfriend, Diego. Cleveland is off trying to save her.moreless
Donna asks Cleveland to spend more time with Rallo. Cleveland joins Rallo in his favorite hobby, "mutton bustin'" -- in which he rides a sheep like a bull in a rodeo. Donna isn't thrilled and the two have to go behind her back. Meanwhile, Cleveland Jr. is jealous.
Coach Cleveland gets greedy to win the high school baseball state championship game and turns to cheating when his star pitcher Oliver Wilkinson gets mauled by Mr. Waterman's rabid dog. This causes Cleveland to disguise Holt as a teenager.
After getting beaten by Lester in a game of baseball, Cleveland loses his confidence and tries to think of a way to get it back.
In this special "live" episode, Cleveland and Donna try to celebrate their anniversery, but keep getting interrupted by different events that are going on, including Roberta going on a druken rage because she was written out of the episode and Tim finding out that Arianna is cheating on him with Donna's ex-husband Robert.moreless
When Cleveland finds out that the kid he use to pick on when he was kid grew up to become President Obama, he begins to wonder what he has done in his life. He decides to go into the music business with Kenny West, but Cleveland soon learns how harsh it is in show business when Kenny dumps him to go solo. Meanwhile, Rallo begins a relationship with Kenny's daughter Candice, but soon regets it when he discovers how pushy she can be.moreless