When Jackson was 10, his family moved nearly 2000 km north to Karratha after his father was offered a job as the primary school principal. He became head boy at Karratha Senior High School. At 17, Jackson went on a year-long Rotary exchange to Brazil. He returned home with a large circle and symbol tattooed under his left bicep.
In 2011, Jackson moved to Sydney to join National Institute of Dramatic Art (NIDA). He graduated from NIDA in 2013 and returned to the metalwork factories and engineering workshops of Karratha.
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. In September 2015, Jackson starred as Peter Allen in the 2-part -mini-series of his life titled Peter Allen : Not the Boy Next Door. In December 2015, at the Australian Academy of Cinema and Television Arts Awards, Jackson won best lead actor in a television drama for his role as Allen. In May 2016, at the 58th Annual Logie Awards, Jackson won Most Outstanding Newcomer for his role as Allen.
In February 2017, Jackson will star alongside Heidi Arena in the Melbourne Theatre Company's performance of Born Yesterday.
