This chapter looks at Sun City, the massive resort and casino that opened up in Bophuthatswana in 1979. Just a 2-hour drive from Johannesburg, Sun City was a massive entertainment complex that served as the most visible symbol of the Bophuthatswanan state. Part of Sun City’s appeal was that it flouted many of the laws in the Republic, most notably apartheid’s racial segregation and prohibitions on miscegenation, as well as South Africa’s proscriptions against gambling. Sun City was an important flashpoint in the battle over Bophuthatswana’s contested sovereignty, especially because it attracted marquee sports and entertainment figures who were willing to break the anti-apartheid cultural boycott. The contours of these battles were often counterintuitive and surprising. Frank Sinatra’s opening of the Superbowl venue in 1981 began the short golden age of Sun City that would last until the release by Artists United Against Apartheid (AUAA) of the “Sun City” in 1985. Thereafter, the cultural boycott applied equally to Bophuthatswana as it did to South Africa proper.