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.

Vivian trusts Wil and Carlton to take her heirloom bracelet to the jewelry shop to have it reset. Before they do that, Carlton tells Wil about a hot insider tip he got on a company's stock, and they can make thousands. They don't have the money to buy the stock, but the boys figure the appraised value of the bracelet will easily cover its cost. So, they take it to the pawn shop and sell it, then buy the stock. That night, they watch a news report where the company has announced bankruptcy. Uh oh - now not only have the two lost money on a bad tip, they don't have any money to buy back Vivian's bracelet. The two scramble for ways to raise the $500 needed to buy back the bracelet ... and decide the best option is to take jobs as male strippers. When they accept the job, they are told they will be the main entertainment at a party for a socially elite organization - unknowing that Hillary and Vivian are among the guests. Carlton is making loads of money with his sensuous routine, and the girls are begging him to take it off - then Vivian walks in and demands, "Put it on!" At home, Wil and Carlton now have no choice but to explain everything. The entire story makes Phil extremely furious, and he tells the boys in no uncertain terms to do whatever it takes to get the bracelet back, or they will be arrested on federal charges. At the pawn shop, they find themselves at odds with a customer who wants to buy the bracelet ... and Carlton is backed into a corner when, after asking what he has to do to get the bracelet back, the rotund, ugly owner makes a suggestion.

Will gets arrested for numerous outstanding parking tickets.

Philip hires an ex-convict as a handyman, and the Banks house is robbed, but who did it?

Will and Carlton are at the ATM and somebody tries to kill Carlton for his money, but Will takes the bullet for him.

Still in the hospital from being shot, Will thinks about his future. He asks Lisa to marry him.

Will finds out what it is like to have a woman in his life that controls things. Also, Will lands a part in a soap opera and begins to see himself as a major star, spending money to fit his new status.

Will, in his new job on Hillary's show, over medicates Hillary and has to try and protect her chances at getting a new sponsor.