This episode explores certain 90s hip hop groups and artists who embrace and glorify capitalism. The first segment discusses Strain Theory, the idea that the American Dream encourages its realization even through criminal enterprise. The second segment discusses the Mafioso Rap of Kool G Rap, Raekwon, Jay-Z, and Big Pun; while the last segment looks at Puff Daddy and particularly at "It's All About the Benjamins."