A streetwise teenager is sent by his mother to live with wealthy relatives in an upper-class California neighborhood, where he must adjust to a new lifestyle.

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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.

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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.

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Philip's parents come to visit for the weekend when he wins a prestigious award. After finding the rehearsed lines of the Banks' to be boring and deciding to kill the story, Will talks to the interviewer telling her embarrassing stories about Philip's past "barnyard life" he heard from Philip's parents.

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Will gets a visit from an old pal named Ice Tray, who, to Vivian's and Philip's dismay, warms up to Hilary.

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While Philip and Vivian go on a trip to Palm Springs in Mr. Furth's helicopter, Will and Carlton drive Furth's car there as well. They get pulled over for "stealing" the car. Hilary babysits Ashley as Geoffrey has the weekend off.

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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.

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The family heads to the mall to pick up costumes for Hilary's Halloween Party, while Will and Carlton place a bet to see who can find a date for the party. Philip gets held up at a gadget store. Vivian sing in a Record-A-Song booth. Hilary forgets to take a hat off Ashley and walks out of the store with it, they get accused of theft.

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Will and Carlton both try to win Melinda over by making up stories about themselves. She ultimately chooses Carlton over Will, though she hides a secret.

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It is Geoffrey's birthday and Will decides to set him up on a blind date as a gift. Will winds up thinking she is perfect and breaks up the two dancing at a nightclub. Later when Geoffrey comes home, he gives Will Helen's phone number stating she would be more fit for Will.

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

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Will's taskmaster mother visits for the holidays and puts the kids to work preparing a thanksgiving dinner, but preparations soon go awry.

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Hilary rats Will out for several things including getting in at 3 in the morning the previous day in order to get the family car instead of Will. Will plans revenge, while going to find out where Hilary is shopping he learns that she dropped out of college three months ago. Will uses this in order to get Hilary to slave for him while he is punished. Hilary tries to get Carlton to go against Will, but he also uses it against her.

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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.

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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.

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One of Philip's clients is very superstitious and befriends Will because of a couple of coincidences. He thinks Will is his good luck charm and lets Will make some major decisions.

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Will proposes a black history class be instituted at Bel-Air Academy, and gets a surprise when Aunt Viv arrives to teach it.

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Philip's mother joins the family for the weekend after recovering from a cold, Philip wants her to relax for the weekend but she wants to be more active.

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Jazz asks Will the favor of taking his sister out on a date after she moves into town, Will turns it down until Jazz introduces the two. Will takes her on a date and learns that she has her whole life planned out for the two already.

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Geoffrey's old employer Lord Fowler and his daughter come to the Banks' house for the weekend. Will wants to use the car to go to a Ziggy Marley concert in Nevada, Philip and Viv won't let him so he makes a proposition to be on his best behavior for the week. Lady Penelope winds up not being what Will thought she was.

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One of Vivian's students, Kayla Samuels comes over for dinner and Will tries to impress her but fails. It upsets Will that he fails so the next day they have an argument but wind up liking each other. Will starts taking time away from her studies and Aunt Viv tells him to cut back on seeing her so she can have a good future ahead of her. Vivian winds up lecturing Kayla and revealing things about her struggle to be successful.

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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.

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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".

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Ashley's birthday is nearing and when the family asks her what she would like for her birthday shows a picture of a boy, Little T. Hilary knows T's agent so she has him come to Ashley's birthday party to perform a song for her. They hit it off and set up a date for the next day. Will and Carlton disagree with the date, so they decide to follow them on their date.

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Hilary lands a new job as an assistant to an actress, Marissa Redman. Ms. Redman turns out to be completely bossy. Will surprises Hilary with Jazz in the office and Marissa takes a liking to Will, wanting to bring him to a restaurant opening, she puts Hilary's job on the line if she can't set the date up. Will will only do it if Hilary goes on a date with Jazz.

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