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When Ashley decides she wants to have another baby, Winston laughs in her face. But when she begins shopping for a sperm donor, Calvester must help Winston stop the stork!
Winston's large real estate plan falls through and he reluctently uses Calvester's phone to look up all of his rap star contacts. But all comes to a head when Twista the rapper shows up to claim his cell phone from Winston.
Cali Cal is informed by the probation authorities he has to have a full-time job or go back to jail! In a bind, Calvester fakes a disability to work at a lingerie store but has to jump through hoops in order for no one to find out he's faking it.
An old college buddy visits Winston when he comes to town. But Winston's acceptance is put to the test when he discovers his football-playing friend Moose made a big decision, changing genders. Will things change between him and his old friend?
Ashley's rich mom Maggie falls for Calvester's persuasive charms so Ashley and Winston try to speed up the wedding to get Calvester out of their home. Is Maggie going to take Calvester off the market or will he continue his bachelor life?
Calvester gets a new job as an assistant to a notable photographer. But the picture doesn't stay perfect for long when it's Calvester's job to keep the new boss from publishing revealing photos of a young Ashley.
The Hill's get new neighbors, single-mother Brenda and her daughter Jamilia, and Calvester is ready to flirt! But when Brenda puts Heather too urban Mrs. Hill goes to desperate measures to get things how they used to be.
When the Hill household hits a budget crunch Winston invests money in a website won by his alleged brother, Sean. But when Sean shows up at the Hill's door one day they have to decide if he's really blood or a con man. Before the rest of the family decides, Calvester already is certain he's no blood relative of him.
In a money-making scheme, Winston Jr. decides to become a gangsta rapper. But his new change gets the Hill clan in a battle with a real-life gangster rapper. Will Winston Jr. go back to his conservative ways before it's too late?
A bully from Calvester's childhood is back as his new parole officer and that's not good news for Calvester. But when the bully goes too far when he abuses his power by moving in and making them wait on his every whim, they must come up with a secret weapon, and fast!
Calvester's former cellmate, Jamel, drops by the Hill household and impresses the family with his knowledge of the stock market. Everyone is very fond of Jamel except Calvester, who is unsure of Jamel's
Calvester's scary former cellmate, Punkin, decides the Hill's house is a perfect place to live, except for one problem: they want him out! Afraid to be honest, the Hill's feel like prisoner's in their own home. When Punkin has romantic interests in his daughter, the family must band together to kick Punkin to the curb!
