Jacky opens with the reunion of two very different brothers. The title character (Guy Simon) is a city slicker in Melbourne who’s planning his future: he has dreams of home ownership and, with the help of an employment agency, is about to finally leave the gig economy for full-time work. His younger brother Keith (Ngali Shaw) – “everyone’s favourite liability” – can barely hold down a job, and has come down from “the Mish” to crash on Jacky’s couch, ordering Uber Eats for every meal and rarely changing out of his trackies.
Keith’s arrival throws Jacky’s compartmentalised life into chaos, or at least puts two of his core relationships with white people under the microscope. Linda (Alison Whyte), a kind but culturally clueless woman, is helping Jacky (and eventually Keith) into stable work through an Indigenous community program in desperate need of funding. A transactional relationship becomes knottier as Jacky spends more time with his sex work client Glenn (Greg Stone), a bumbling recent divorcee wanting to explore a long-held racial fetish.