He first began playing guitar at age 14 and supported Birds of Tokyo, Megan Washington, Diesel and Ian Moss in Karratha.
[1] In 2014, Jackson auditioned for a single scene role in the mini-series Deadline Gallipoli but was later offered the lead part of Charles Bean alongside Sam Worthington, which aired on Foxtel's Showcase in April 2015.
[3] In February 2017, Jackson starred alongside Heidi Arena in Melbourne Theatre Company's performance of Born Yesterday.
[4] In December 2018, Jackson released season one of his podcast The Good Thief[5] in which he interviews some of Australians including Jack Ellis, Anna McGahan, Glendon Ivan, and Samuel Johnson.
The same year, he played alongside Harry Potter’s Miriam Margolyes, and Australian actors Richard Roxburgh and Deborah Mailman, in the role of Rich Uncle Brian in H Is for Happiness.