S1E10 · A Hit is a Hit

Chris tries to fulfill his girlfriend Adriana La Cerva 's dream of being involved in music production by meeting with a gangster rapper, who is in a dispute with Hesh about royalties. When he and Hesh agree to sue each other, Tony's crew mocks the rapper for going through the legal system. Adriana's first recording goes poorly and Hesh rejects their material. Tony's neighbor Bruce Cusamano invites him to play golf with his friends. They make Tony uncomfortable with questions about mob life, and he tells Melfi about a boy from his childhood with a cleft palate he and his friends used to mock, only understanding his pain after being humiliated at the club.

As revenge, Tony pranks Cusamano by filling a box with sand and leaving it with him to hold on to, and he and his wife Jeannie nervously try to guess what illegal contents may be inside.