The chapter contributes to a critical discussion of cosmopolitanism by examining the affinities between the cosmopolitan subject and the stranger as conceptualized in the social sciences. The similarities between these two social actors are manifested in the cosmopolitan outlook/disposition espoused in contemporary versions of cosmopolitanism. Drawing on the work of Simmel and Bauman, the chapter outlines the major characteristics of the stranger and, through an investigation of various cosmopolitan thinkers, we delineate a cosmopolitan world-view. This comparison leads to my central thesis that a new social type has emerged which can be categorized as the cosmopolitan stranger. The chapter demonstrates how cosmopolitan strangers develop a more perceptive, broader and keener insight than those confined to either a particular or universal perspective. As a consequence of this enlightened view, these new social actors undermine binary logic and the essentialism underpinning 'standpoint epistemology". We begin with an investigation of the stranger in sociology, and then provide a brief examination of the major attributes of the cosmopolitan disposition and conclude with a critical assessment of the cosmopolitan stranger.