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Un chico de Filadelfia es enviado por su madre a vivir con su tía, tío y primos en su mansión de Bel-Air.

Will makes a bet that Carlton wouldn't last a weekend in Jazz' neighborhood, Compton. Carlton starts to fulfill the bet, by not only fitting in, but getting along with the guys in "The Hood". Will has to find a way to stop him from going to MacArthur Park at night, to "Hang with the crew".

When Philip backs out of taking Vivian to Lamaze class, Will reluctantly offers to be her coach. Will meets a single pregnant woman who is a sportswriter. She invites Will to attend a game with her, where she goes into labor.

The Oprah Show personnel contact Philip Banks to appear on the show with his family. The Banks travel to Chicago and Will is ecstatic. Unfortunately, he is not invited to be part of the show.

Will's friend Keith, a comedian from Philadelphia, visits Will and the Banks family. His sense of humor tickles Will's funny bone, causing Will to think that a career in comedy might work for him, too. Meanwhile, Vivian is away and Phillip demands the attention of his children in her absence.

Philip loses the judge election, and Judge Robertson and Will have words. Judge Robertson dies after the argument. Philip gets appointed Judge.

After Ashley reveals to him that she does not enjoy playing the violin he takes her to and trades her violin in for a drum set. Then reveals that he has already hired Ashley a teacher. Jazz.

Vivian goes away to Berkeley for the weekend, leaving Hilary in charge of the house while Philip is at the office. Will steals the car keys to go to the pool hall he winds up losing his money and the car to a hustler. Philip goes down to the pool hall to claim the money back, playing the hustler.

Will is stunned when Ashley asks him a question about the birds and the bees.

In order to spent time with them before they go off to college, Phil takes Will and Carlton camping and things go terribly wrong.

The family gets ready for the baby, and Ashley is jealous.

Will drives without car insurance, and faces the consequences.

Will finds out that his mom is seeing a new man while on a holiday skiing trip to Utah. When the adults go out to the lodge for the Christmas party, a knock on the door brings the kids trouble.

Will tries to impress a girl's father so he can date her. Mr. Banks, Carlton, and Geoffrey try to teach him how to be a gentleman in a My Fair Lady way.

Jazz stays at the Banks house when he has no place to go. Hilary must do community service at the clinic after going to court for parking tickets. While there she meets a doctor.

Will's talents help him become a basketball star at school, but cause Carlton to begin feeling insignificant and inferior to him.

Ashley and her friends ask Will to tell a scary story at their slumber party before they go to sleep. Will tells the tale of his first day at Bel-Air Academy.

Will realizes that Ashley has never experienced a real Christmas before and goes out of his way to let her have one. He decorates the inside of the mansion and also the outside fully, upsetting some of the neighbors.

Will enters into an after school program, following the girls into a Poetry class he makes up a poem on the spot to impress the girls. After creating a poet, Christina asks to bring the made up poet to Poetry Night. After Jazz doesn't come through with an impostor, Will uses Geoffrey as the fake poet.

Phil and Vivian feel that Will and his new girlfriend are moving too fast.

Philip tries to work on repairing things in the house. Will goes on a game show and he must decide which of his friends will be his partner.

On the same day Will finally has a date with Jackie, he has the opportunity to go to the Playboy mansion because Hilary, much to the dislike of Uncle Phil, has been asked to pose for Playboy.

Geoffrey falls for the woman next door while thinking she is a butler. When he finds out she is just visiting and is worth 25 million dollars he must decide whether he wants to continue seeing her, or not.

Philip gets upset when he sees his mother spending time with a new man. The kids bet each other that they can't do something the other sex would normally do.

Much to their surprise, the family learns that Vivian's sister is engaged to a white man.