This dissertation examines the lives, roles, and impacts of above-ground burial markers in shaping socio-cultural dynamics within and across communities in fourth- to first-century BCE Sicily. Previous scholarship on this subject has primarily focused on the cultural origin of material culture classes, including funerary monuments, heavily relying on categories such as Syracusan (Greek), Roman, and Punic. Often leaving these labels undefined, scholars have generally applied them to entireclasses of artifacts, flattening variability across communities and obfuscating material culture’s diverse roles across time and place. Countering this tendency, this dissertation examines the history and use of epitymbia, aboveground funerary monuments dating to the last four centuries BCE through three perspectives: as a Sicilian expression of a Mediterranean phenomenon; as a regional trend in conversation with the political changes occurring on the island; and as individual monuments with unique histories and biographies, which interacted with and (re)defined relationships across and within local communities. Owing to their popularity and ubiquity on the island and the presence of comparanda across the Mediterranean, epitymbia constitute an especially apt body of evidence for exploring the role of connectivity and socio-cultural dynamics in Sicily as well as the island’s connections to the broader Mediterranean. The case of epitymbia demonstrates that despite the popularity, roles, and functions material culture classes may have, they can eventually fall out of use without evolving into something new. Countering teleological narratives about the inevitability and continuous transformation of ‘global’ phenomena, epitymbia show the range of different trajectories, uses, and developments the same ‘global’ material culture class can undergo. Secondly, while maintaining significant morphological similarities through time, material cultural classes’ roles and impact can change. From being a means to negotiate people’s status and belonging within individual necropoleis, to becoming powerful statements signaling individuals’ and communities’ roles in the new political landscape, epitymbia’s role shifted across different socio-cultural and chronological contexts. Ultimately, by shedding light on the history of the island and its funerary evidence, this dissertation contributes to current archaeological debates about ancient connectivity and the role and impact of material culture within this phenomenon.