Ep 24 | Andrew Hamilton: From Prison to Punchlines – Owning the Comeback

Join hosts Jamie Small and co-host George Azzi for a raw, hilarious and inspiring conversation with comedian, author and OJ Crew creator Andrew Hamilton. Andrew opens up about his extraordinary journey from high-level drug dealer and jail time to rising stand-up star. He reveals the life-changing moment in Long Bay prison when a voice told him comedy would change his life, how he started writing jokes behind bars, tested material on his cellmate, and went from open mics to performing at the Melbourne Comedy Festival after just one year — earning a Best Newcomer nomination and a book deal. The boys dive deep into his no-BS mindset: writing 1,000 words a day (Stephen King style), the discipline required after early success, why drug money is easy but earned money hits different, and the power of publicly owning your mistakes. Andrew shares wild stories including the Raptor Squad raid that birthed his first joke, a legendary hot sauce incident involving his girlfriend, milk, and an emergency dick-dipping situation, doing stand-up inside Silverwater Prison for 100 inmates, and facing the podcast’s infamous physical challenge — chili eating and sniffing salts — like an absolute champion. They also cover building the viral OJ Crew YouTube channel, attracting cops, crims and everyone in between to his shows, advice for aspiring comedians (it’s a numbers game — post fearlessly, bomb often), relationships, his supportive girlfriend, and why good times can create weak men while adversity forges character. It’s unfiltered, funny as hell, and full of hard-won wisdom about resilience, extreme ownership and turning the lowest point of your life into your greatest asset. Sponsors Those Ones Underwear – https://www.thoseones.com.au/ World Gym – https://www.worldgym.com.au/gyms/macq... The Grey – https://www.thegrey.au/ Recorded and produced at The Grey Creative Caringbah.