Based on archival research, the Arabic press, and artist memoirs, this presentation argues that the origins of a popular entertainment district in Cairo can be traced back to elite investment in a curious building. Ordered by an elite Ottoman Egyptian, Muhammad Ali Celal in 1896 from the architect A. Lasciac, the Club des Princes housed a stage, relaxing rooms, and administrative offices. The building and the territory around it was bought and united with the waqf of Zeynep Hanım by the private administration of Khedive Abbas Hilmi II. This caused one of the most intriguing court process in the history of modern Egypt because Sait Halim Pasha, a rival of the khedive, was the administrator of that waqf. Legal history aside, the elite investment and common ownership made possible the creation of ‘Imad al-Din street which from the 1910s was the principle artery of Cairo entertainment. Around the Club theatres, casinos, revues were established catering to the rising Egyptian middling classes in Cairo. This also involved the move of fashionable nightlife from Azbakiyya to Tawfiqiyya. Next to the Club, the Ramses Theatre of Yusuf Wahbi and the theatre of Rihani were rivals from the 1920s and tried to cater art to the upper middle classes. This story demonstrates the dynamics of capitalist economics behind urban entertainment.