4. Bourgie Sings the Blues

Carlton is worried about his interview with a Princeton University representative ( Kevin Brief ). In an attempt to clear his mind, Carlton flees to a blues bar, where Pappy ( B.B. King ) is playing, and confesses to Will that he no longer wants to attend Princeton and instead wants to live out in the bar. Will is convinced he is talking nonsense, so to secure Carlton his place at Princeton, he poses as him for the interview. Milo Ventimiglia, who later became known for his role as Jack Pearson in This Is Us, has a role as a guest at Ashley's party.