In this essay, I evaluate Istanbul’s Beyoğlu as a hybrid and negotiated space and investigate how the imaginary and lived experiences of space enable as well as constrain transgressive everyday practices and identity politics. Through analyzing memories, imaginations, and experiences of Beyoğlu, in particular its drag/transsexual subculture, I explore the ways in which the past and present interact under the dynamic of globalization and (re)produce Beyoğlu as a space of difference and containment. Beyond the intricacies of Istanbul’s sex trade, night life, and queer subculture, I propose that the singular district of Beyoğlu, given its geographical, historical, and social location, operates as a microcosm of the tensions and negotiations between East and West, local and global, past and present.