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Comedy review: Jokes About the Time I Went To Prison, FRINGE WORLD

'Fear and Loathing in Las Vegas' meets 'Shawshank Redemption?'
A man, Andrew Hamilton, in a green top. He is smiling and holding a microphone.

Andrew Hamilton saunters onstage with the casual air of someone who’s just popped in to The Federal Hotel for a pint, not someone who’s about to dissect his four-month stint in maximum security in a FRINGE WORLD show. But that’s precisely the disarming charm of this Sydney comic. In Jokes About the Time I Went to Prison, Hamilton delivers exactly what the title promises – a hilarious and surprisingly insightful hour of stand-up mined from his experiences on the wrong side of the law.

Hamilton has a knack for finding humor in the darkest of places. He recounts his prison misadventures with a self-deprecating wit, painting a vivid picture of life behind bars. His first two weeks he had to be in isolation because of COVID. He was so bored he took to writing reviews of the prison food. He reads one out, “Lunch today was a corned beef and honey mustard sandwich. My fiancé called to say she was breaking off the engagement and rehoming my dogs. This quite seriously affected my enjoyment of the sandwich.”

The comedian spent 15 years dealing magic mushrooms and MDMA before a police raid landed him in a maximum-security prison during COVID. Before his arrest he also made popular comedy videos on YouTube and laundered money through a pizza place he set up in Kings Cross. (Apparently his nan was a pizza. Her name was Sue Preme.) He also had a successful job in public relations and a pretty hefty cocaine addiction. He is surprisingly sanguine about his experience at Parkleigh Prison during the pandemic. “Everyone else in the world was either isolated and lonely or hating each other. I was playing touch football, getting off the drugs, eating healthy, making new friends and using my sense of humour to get by.”

He delivers hair-raising tales of drug-fuelled escapades with a mischievous glint. The audience on the night ArtsHub attended were screaming with laughter and this reviewer was in stitches. His stories are not for the prudish or fainthearted – they’re raw and honed with the kind of dark gallows humour you’d expect to come out of a maximum-security prison. 

But it’s not just the outrageous anecdotes that make this show zing. Hamilton is a skilled storyteller, weaving his experiences into a compelling narrative that explores themes of redemption, self-awareness, the absurdity of the criminal justice system, and changing laws and attitudes to drugs. He’s not afraid to poke fun at himself, acknowledging his own flaws and poor choices with refreshing honesty. He also points out that it is now possible to obtain MDMA, magic mushrooms and ketamine legally in Australia for medical purposes. “So really,” he jokes, “according to today’s standards, I was just an unregistered medical practitioner!”

While some jokes tread familiar territory (prison food and dodgy cellmates), Hamilton’s sharp writing and charismatic delivery elevate them beyond cliché. He has a natural confidence, strong stage presence and an easy rapport with the audience, making you feel like you’re sharing a pint with a funny mate down at the pub. Best of all, his show concludes with a positive message about renewal, hope, redemption and following your dreams. Now off the drugs, broke, living with his parents and pursuing a career in comedy (which recently had him nominated a Best Newcomer Award at the Melbourne International Comedy Festival), he says he’s never been happier.

Read: Comedy review: Feeling Afraid As If Something Terrible Is Going To Happen, Arts Centre Melbourne, Midsumma Festival 2025

Hamilton’s endearing charm and honesty combined with a killer wit, deadpan delivery and hair-raising drug stories make for a compelling and utterly hysterical night of comedy. This ex-drug dealer ex-con is a rising star on the Australian comedy circuit and a person to watch. His opening night at The Federal Hotel in Fremantle sold out and went off like a frog in a sock. Better snap up tickets while you can.

Andrew Hamilton – Jokes About The Time I Went To Prison will be performed at The Comedy Factory in Fremantle and The Comedy Shack in Wanneroo until 31 January 2025 as part of FRINGE WORLD, before the Melbourne International Comedy Festival from 27 March.

Andrew Hamilton’s book: The Profound Benefits of a Stint in Prison can be bought after his shows and in select bookstores.

Tiffany Barton is an award winning playwright, actor and independent theatre producer who has toured shows to Melbourne, London and New York. She has a BA in Creative Writing from Curtin University and an MA in Writing for Performance at the Victorian College of the Arts.