Benjamin has worked with countless local theatre companies - such as Studio 18, Teatru Malta, and Ħassle Mejjet Theatre Collective - to breathe life into tens of characters. These include 'Pete' in Dear Pete, 'Lamb' in Is-Serra, 'David' in Il-Pożittivi, 'Grillu' in Il-Giddieb Għomru Twil, 'David' in Id-Dnub tal-Magħżulin, and 'Kris' in Il-Manifest tal-Qlub Maqsuma.
Benjamin is also an up-and-coming writer-director. His works include 90 SEKONDA, Popolazzjoni: 4, NOSTRUM, L-Aħħar Siġra, Pandora, and Brad, Ad & Emerald and the Chocolate Factory (for Trikki Trakki 2023). In 2017, Benjamin co-founded the Ħassle Mejjet Theatre Collective.
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