In popular imagery, the littorals of Sulu and Zamboanga conjure visions of pirates, terrorists, and bandits marauding its rough seas, open shores, and rugged mountains. These bleak accounts render the region nothing but a violent and peripheral southern Philippine backdoor inconspicuous to the sophisticated constituencies of the world’s metropolitan centres. Obscured from these imageries are the lasting cosmopolitan traits of openness, flexibility, and reception of local folk to trans-local cultural streams that marked Sulu and Zamboanga as a globalised space across the ages and oceans. The distinctive features of these cosmopolitan sensibilities are strikingly discernible in inter-generationally shared narratives, artefacts, and performances that were continually renewed from the days when Sulu and Zamboanga served as a borderless trading and cultural enclave nestled at the crossroads of the Pacific and the Indian Oceans. These enduring cosmopolitan sensibilities are embodied in the blending, among others, of the time-honoured dance of pangalay and the pop-musical dance genre celebrated on actual, analogue, and digitally-mediated spaces of the contemporary world. Furthermore, these embodied sensibilities are evident in song compositions that proclaim the humanistic themes of hope, peace, and prosperity to their place and the world in ways that exemplify the local people’s broader sense of connections beyond the narrow association of family, community, ethnicity, religion, and identity. This mixed bag of age-old and recent imaginaries and cultural traffic evoke a sociality that link the social spaces of the troubled but once and current globalised region to continuing acts of transcendence in history, memory, and visions of the future. In these marginalized places, we can see an unyielding tradition of cultural re-adaptation and creativity made up of myriad everyday acts that are down-to-earth, pragmatic, interstitial, and practical cosmopolitanism.