Mother of All Grandfathers - S1.E21

After finding out that Chris used his share of Freddie's restaurant as collateral for his own failed restaurant venture, Freddie insists that Chris ask his wealthy grandfather, Carl, for money to pay off the debt. Carl is displeased with Chris' slacker lifestyle and impressed with Freddie's work ethic, so he makes Chris work as his chauffeur to teach him a lesson about money and responsibility. When Chris feels humiliated, he pushes back, and the result is that grandfather pays off the loan but takes Chris's trust fund and condo in return. So Chris ends up homeless at Freddie's already crowded apartment.