Delhi as it stands presently is built on the ruins of several pre-existing urban centres and is supposedly located on the mythological site of the ancient city of Indraprastha. It is also a classic example of what anthropologist Robert Redfield had defined as an orthogenetically evolved city and what Sjoberg had defined as a ‘pre-industrial’ city. The present city, now a global metropolis, is nevertheless rooted in the seventeenth-century imperial city of Shahjahanabad, built by the Moghul emperor Shah Jahan. This chapter will briefly trace the evolution of this historical city from its medieval roots to its transformation into the capital of a colonial empire with the building of New Delhi. The emphasis is more on the past and on the cultural, social, and political roots of the emergence of the syncretic culture recognized by all who identify as ‘Dilliwale’. The nucleus of this Dilliwale culture lies in its heart, in the walled city, but it continues into the aristocratic bungalows as well as the lanes and by lanes of a city that is always and still expanding. In spite of its growth Delhi still retains its pockets of antiquity as well as the communities that have been its part, since its inception. Traditional institutions like jati, biradari, religion, and regional ethnicities continue to play key roles in the lives of the people of this metropolis, giving its urbanization a colour that is distinctive and has its grey and dark sides as well as the ones with hopes for a resilient future. This chapter endorses the observations of scholars of Indian cities that they are Indian before they are cities.