Malcolm & Eddie (1996)

S4E9 Fairly Decent Proposal

During a trip to Las Vegas with Malcolm and his latest girlfriend, Eddie finds himself drawn to the excitement of the craps table. However, his fortune takes a nosedive, leaving him $50,000 in the hole. Desperate for a solution, he encounters a rich woman willing to erase his debt, but her price is steep—she demands a night with Malcolm in exchange for her generosity.