Leon Filewood is a Torres Strait Islander comedian with Cape York Peninsula connections who has taken a unique path to the stage. His journey, rooted in a desire to protect and empower his community, has led him from the courtroom to the comedy club, blending social commentary with sharp wit.
Driven by a passion for his community, he initially pursued a career in law. "I was worried about my community," Leon explains, "I thought, well, if you know the laws, you can protect your people." He also had aspirations to join Parliament at some stage. He practiced in crime and family law, later transitioning to commercial litigation, insolvency and bankruptcy, before becoming in-house counsel for an organisation.
Despite his legal career, comedy was always a lurking interest. Inspired by comedians like Jerry Seinfeld, Eddie Murphy, Richard Pryor, Trevor Noah and Chris Rock he admired their ability to connect with audiences and spark laughter. He was fascinated by Seinfeld who could get on stage in a suit and talk, and people would laugh and like him. But it wasn't until his 30s that Leon decided to take the plunge, thanks to the Melbourne International Comedy Festival's "Deadly Funny" program.
"Deadly Funny" provides a platform for Indigenous Australians to explore comedy. Leon attended a workshop led by comedian Andy Saunders, who encouraged him to perform at a community show in 2017 in Brisbane. "I got on stage and did three minutes," Leon recalls. "I got laughs and just been addicted ever since." He credits "Deadly Funny" for giving him a start in comedy, emphasizing that without the program, it would never have happened.
Leon's legal background evolved into a career in community development, and he now works as a senior consultant for a professional services company. His role involves ensuring that major infrastructure projects engage with First Nations communities respectfully, adhering to principles of self-determination and free, prior, and informed consent. Leon emphasizes the importance of partnerships and co-design, aiming to leverage economic opportunities for communities while protecting their cultural heritage. His job involves educating clients and communities about projects and potential opportunities, leveraging the best outcome for country, community, and culture.
Balancing a demanding professional life with comedy is a challenge, but Leon finds that the two worlds complement each other. His reputation as a comedian can often ease his interactions within communities, fostering trust and rapport. "If they already know me, then they already have a sense my comedy is very authentic, so they already have a feel for me, which allows that respect to come quicker or sooner".
In 2025, Leon will premiere his first solo show, "Whichway". Inspired by the rise of fear-mongering rhetoric during the federal election, Leon felt compelled to use his platform to address critical issues facing First Nations Peoples. "I was like, Nah, I got to do something," Leon explains. "I can tell jokes and get on stage."
His comedy touches on race-related issues, observations of both white and Aboriginal culture, and everyday experiences like traveling and airport security. He also incorporates jokes that are not explicitly about race, using them as opportunities to expand his comedic range and offer audiences a break from heavier topics. His comedy is observational of white and Aboriginal culture, and the experience of being a black man in Australia. He aims to create comedy that is both thought-provoking and entertaining, encouraging audiences to laugh, reflect, and engage with the deeper meaning behind the jokes. "My comedy is about education," he says, aiming to leave the audience thinking about the subtext of his jokes.
As a recipient of the Fringe Fund, Leon is grateful for the support that has enabled him to share his unique voice and perspective on stage. He, premiered the show on Tuesday the 5th on Kaurna Country, was proud to know he will have Kaurna Elders in attendance.
Learn more and find tickets here.
Watch Leon's Deadly Funny set below.