Theo's Holiday
S2:E22
1986
IMDb
After Theo claims that he'll have no problem making it in the "real world", the Huxtables convert their house in the "Real World Apartments" and teach him a lesson about the real world; i.e., needing employment and references to get an apartment, income to get a bank loan, having to pay for his meals, etc. Carl Anthony Payne II as Cockroach.