Will persuades Ashley to pawn her violin for a drum set.

Will wants to go out with a beautiful girl he meets at the country club, but first he must figure out how to impress her extremely snobbish and very protective father so he seeks tips from cousin Carlton on becoming preppie.

Will tries to smooth things between Philip and his very rural parents when they visit to see him receive an award.

Jailed, Will and Carlton stage a media stunt.

Will joins his prep school's poetry club.

Carlton and Will, babe magnets. Who will be first to get a date for Hilary's Halloween party?

Carlton and Will, babe magnets. Who will be first to get a date for Hilary's Halloween party?

Happy birthday Geoffrey! For a gift, Will tries matchmaking, then falls for Geoffrey's date himself.

Carlton feels overshadowed by Will, who's become a basketball star at school.

A holiday visit from Will's taskmaster mother puts the kibosh on conspicuous consumption and puts the kids to work preparing Thanksgiving dinner.

Hilary becomes Will's personal maid when he threatens to disclose she's dropped out of UCLA.

Will tells Ashley's slumber party guests a scary tale about his first day at Bel-Air Academy.

Will inimitably dresses the mansion for the holidays, to the dismay of the neighbors, including heavyweight boxing champion Evander Holyfield.