Iliza finds out the the music she "listened to growing up" was created by a man only three years old than her. Rapper/tech guy Chamillionaire joins Iliza as they dive deep into the transformation of rap over time, the relation of fame in comedy to fame in rap, fan expectation and authenticity. Cham shares about his interests in the tech world, Iliza explains the story of how they met (she called him 50 Cent) and then attempts to explain why women are so confusing. Iliza takes issue with Cham living in Marina Del Ray and he defends it. They discuss ugly faces, evolution of artists and Cham goes on record as promising Iliza a role as a booty girl in his next video.