In "A Cleveland Brown Christmas", Cleveland and Donna shopped at Lester's Christmas tree shop, for a new Christmas tree. Rallo picked out a very lame one and Cleveland hesitantly allowed him to buy it, after hearing Donna tell him that she's been allowing him to pick out these trees, ever since his real father, Robert left him. At Mr. Waterman's Christmas party, Cleveland worked as a Sit-Down Santa. Rallo, who believed he was the real Santa Claus, trash-talked Cleveland in front of him. Cleveland got triggered by Rallo's constant slander of him and then Cleveland told Rallo the truth about his father. Donna was mad at Cleveland for this, because Rallo was actually scared by who he thought was Santa Claus. Cleveland went to the strip club to find Robert and convinced him that the best gift to give to Rallo for Christmas, was just being present. Cleveland also went to the house on Christmas, dressed as Santa in an attempt to brighten up Rallo's Christmas day, but this failed. Then Robert came in doing the same thing, and revealed his true identity. Rallo was reasonably confused. Robert lied to him, saying that he was Santa Claus, and Rallo bought it. It was then revealed that Cleveland was the fake Santa and Rallo went back to hating him, but also went back to loving Christmas.
In "Murray Christmas", Cleveland goes to see his father, Freight Train, who's forced to admit he is getting old and regrets not spending more time with Cleveland even if in the form of more beatings. Cleveland was pissed off with his dad's constant disrespect and thought it was about time to put him in his place. Cleveland gets into a boxing match with him, and now that his dad is frail, weak, and senile, Cleveland horribly beats him senseless, kicks him while he's down, and knocks him out cold, nearly killing him. After a quick trip to Dr. Fist's office, Fist says that he'll be fine, and Cleveland celebrates his victorious beat down of his father.
In "Die Semi-Hard", Cleveland tells his family his own version of one of his favorite holiday stories, “Die Hard”, to help pass time while posing in a holiday nativity scene. In it, he plays the role of Bruce Willis, but still going by his own first name, just to avoid the confusion. After detective Cleveland Willis flies into Los Angeles to meet his wife at her job at Waterman International, he tells his limo driver Rallo about some of his marriage troubles while he hopes to reconcile during the office Christmas party. Meeting with his wife, he takes off his shoes and tries to be romantic but Donna resists his charms and returns to the party alone.
Meanwhile, a group of thieves led by Tim posing as terrorists take the party guests hostage and separate Mr. Waterman in order to gain access to the Waterman International vault. Cleveland tosses his shoes out the window over a nearby poser line when he hears gunshots and arrives as Mr. Waterman is killed. Hearing noise from Cleveland, Tim sends Kendra out to investigate where she is killed by Cleveland. As the terrorists discover Kendra's body, they hear Cleveland trying to use his radio to call for police and start shooting. As police surround the building, Cleveland taunts the terrorists but slips and gives away his location. Tim manages to come up with a name on the office list and fools Cleveland who gives him a gun which her turns of Cleveland. Cleveland manages to distract him momentarily and takes out another of the henchmen as he escapes. As Cleveland hides behind a wall of glass and keeps Tim and Lester pinned down, Tim orders Lester to shoot out the glass after noticing Cleveland’s bare feet. Cleveland is forced to retreat through the glass picking up several shards in the process. Despite picking out much of the glass, Cleveland leaves bloody footprints behind him.
The terrorists take Cleveland’s friend Holt hostage but kill him after they learn that they also hold Cleveland’s wife Donna. As Cleveland ponders his next move, Lester manages to sneak up on him but is hung from a chain by Cleveland after telling him that the hostages have been moved to the roof with explosives. Arriving on the roof, Cleveland orders everyone off but the FBI agents in a helicopter mistake Cleveland for one of the terrorists and open fire on him. Tim orders the roof blow as Cleveland ties a fire hose around his waist and jumps from the rooftop. The blast engulfs the helicopter as Cleveland shoots his way back into the building. As Cleveland catches Tim and his last henchman, Tim grams Donna and holds her at gunpoint forcing Cleveland to drop his gun. As Tim thinks he's won, Cleveland draws a second gun taped to his back and shoots Tim and the henchman, forcing Tim through the window, killing him. Outside as the surviving hostages are freed, Donna and Cleveland reconcile and the story ends.
In "'Tis the Cleveland To Be Sorry", Cleveland fakes being homeless so he can get free sandwiches at the homeless shelter. When he's caught for what he does, instead of apologizes, he shames the people who donate to the homeless, for only giving a crap on Christmas. This takes the heat off of him and gets him off scot-free.
The Cleveland Show
- "A Cleveland Brown Christmas"
- "Murray Christmas"
- "A Semi-Merry Christmas"
- "'Tis the Cleveland To Be Sorry"
- "A Very Special Family Guy Freakin' Christmas"
- "Road to the North Pole"
- "Jesus, Mary and Joseph!"
- "The 2000-Year-Old Virgin"
- "How the Griffin Stole Christmas"
- "Don't Be a Dickens At Christmas"
- "Christmas is Coming" (Non-Speaking Cameo)