Benjamin was first exposed to the theatrical arts sphere at the age of 12 when he joined Stagecoach Theatre Arts School. From then on, his love for this art form has only grown, enjoying on-stage and backstage experiences with several theatre groups and troupes, including FMYT, Studio 18, and Ħassle Mejjet Theatre Collective.

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Over the years, Benjamin participated in countless productions and, subsequently, played dozens of different roles. These include Pete in Studio 18’s ‘Dear Pete’, Lamb in Teatru Malta’s Maltese adaptation of ‘The Hothouse’, Max in the online version of ‘Ineż Kienet Perfetta’, David in Culture Venture’s ’Il-Pożittivi’ and Grillu in Studio 18 and Spazju Kreattiv’s ‘Il-Giddieb Għomru Twil’.

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Benjamin’s role within the local theatre industry goes beyond that of an actor. Over the years, he has written and co-written a number of scripts, such as ‘Pandora’ (produced by Ħassle Mejjet Theatre Collective) and ‘L-Aħħar Siġra’ (produced by Just Another Collective and Ħassle Mejjet Theatre Collective for ŻiguŻajg), ‘Help! Barbetti go Bohemian!’ (produced by Studio 18), and ‘iLand’ (also produced by Studio 18).

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In 2017, Benjamin founded the Ħassle Mejjet Theatre Collective together with two of his colleagues. Since then, the collective has welcomed an extra core creative member. The plays produced by the group include ‘An Ode to Teen Angst’ (2018), ‘Pandora’ (2019), ‘An Ode to Teen Angst: The COVID Chronicles’ (2021), and ‘L-Aħħar Siġra’ (2021). Benjamin’s roles in said productions have included actor, writer, and co-director.