Andrew Hamilton hit the comedy circuit a mere two years ago, just after he was released from prison. He initially had to take his mother to open mic nights, and be on stage early, as he was under strict bail conditions requiring him to not only be accompanied by his parents at all times, but also to be back home by 10pm. The police checked.
Nowadays, he may still not be allowed to leave the country, but he can go outside without his mum, and it’s working for him. He’s been selling out his show, “Shit Bloke,” across Australian this year, and the show was very well received both at Sydney Comedy Festival and Melbourne International Comedy Festival. Hamilton is hitting the road over the next few months. When he’s not on tour, you’ll find him 4-5 nights a week at his regular venues across Sydney.
His previous show “Jokes About The Time I Went to Prison” was such a hit he was nominated for Best Newcomer in the 2023 Melbourne International Comedy Festival- no mean feat. On top of all that, this July he has a book coming out with Affirm Press about the profound benefits of a stint in prison.
It’s a lot of work, but something he’s elated to be able to do, not only for himself, but also as a way of giving back to the community. At his sentencing, which took place after his open-mic-on-bail era, the Judge took a bet on Andrew’s risk of reoffending being low, not least because of his burgeoning comedy career, but also because he’d been very successful in the P.R. industry since he was in his 20s. “I think my background in a legitimate career path helped the Judge consider my rehabilitation prospects as strong,” Andrew told Irresistible, “so I suspect it helped him in his deliberations.” He is certainly keen to prove the Judge’s faith in him wasn’t misguided, and it’s all a very far cry from his previous lines of employment.
In 2021 the forces that were carving out Andrew’s life; the successful career in PR, a serious drug habit that had led to even more serious dealing, and the trendy Brooklyn Crispy pizza joint in Potts Point, Sydney, that even served pizza to dogs, collided in spectacular fashion when the police raided his home. His then- fiancée dobbed him in to the cops in the middle of one of their multi- day benders.
They’re on good terms.
Despite hiding behind a door, the authorities quickly found not only Andrew, but enough evidence of his working life to put him on the very wrong side of the law.
It wasn’t the pizza boxes.
What had started out as a hobby growing mushrooms to feed the habits of Andrew and his friends, turned into a massive business that went on for years, involving multiple drugs, and generating “crazy amounts of money.” He believes though, that if he hadn’t been caught, he wouldn’t have survived his own enormous cocaine habit, and that the arrest, jail time, and now his comedy career has quite literally saved his life. He was quickly placed in the notorious Long Bay Correctional Complex, a hard- core prison on the outskirts of Sydney, with hard-core characters, where he soon started dreaming of a second life as a comedian. He was aware though that a one-liner that wasn’t received well could have serious ramifications out in the yard, so he started slow and zoned in on keeping a record of prison food with reviews, which became a hit on TikTok once he was outside. (1.2/10 for a beef salad rates as “tough, even for jail.”) He did eventually find some sympathetic cellmates who were happy to let him try out some material, and even gave him a couple of good stories that he used in his shows.
He toughed it out for 4 months, but once outside on bail he truly had to face how much his life had fallen apart. The pizza shop had soon gone bust as he, “could no longer pump it full of drug money,” and Andrew had filed for bankruptcy. His fiancée had left him not long after he entered prison, and some friends who he thought would be there for him had disappeared.
In the end, all this only spurred him on, and no doubt led to a level of self- deprecation which works brilliantly on stage, as well as a genuine generosity he has for his audiences. His bits are tight and never over- explained, and the set is packed with laughs that just keep coming, while he comfortably holds the room. His audience is broad, but it is not uncommon for the room to be filled with lawyers (his own included), court staff and judges as well as police officers and prison staff on a work night out. He’s pretty sure he’s had quite a few criminals in the crowd as well – they laugh that much harder at some of the jokes.
He hopes to be able to give back at another level one day soon. He’s working to be able to perform inside prisons, or with vulnerable youth offenders who are heading towards jail time, sharing his lessons and the mistakes he wants others to avoid. Laughing and learning in action.
The other thing he’d like to do is travel overseas with his routines, and it seems as soon as his correctional orders are lifted, which apparently won’t be too long, Edinburgh and the rest of the world will be waiting. For now, catch him on tour. As the NSW Police say on his poster, “One to watch.”
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