Australian comedian and former convict Andrew Hamilton to tour NZ, bringing jail jokes and honest humour

For the first part of his stand-up comedy career, ex-convict Andrew Hamilton had to be chaperoned to gigs by his mum. Now, his darkly humorous takes on his four months inside two of Sydney’s most notorious prisons are a hit with audiences online and in person, having amassed more than a billion views.

Mitchell Hageman hears how, from his lowest point, Hamilton used the transportive power of laughter for the better.

Andrew Hamilton wasn’t afraid of embarrassing himself, considering he was already at rock bottom.

Having just been released from jail, he saw bombing on stage at stand-up comedy gigs as a walk in the park.

“I think that, when I got out, I was pretty angry at the world and pretty lost, and so I guess I had the choice between either using that in a destructive manner or in a constructive way,” he tells the Herald.

Today, the TikTok and live comedy star has turned the tables and is using his platform not only to entertain, but also to help those who might have faced similar situations.

Once a successful business owner, a drug-dealing and using habit finally caught up with him in 2021, when police raided his home and charged him with selling magic mushrooms and LSD.

“I was at university, eating and taking a lot of party drugs with friends, and I had some pretty good connections to get them.

“I just wanted to help out mates and make a little bit of pocket money, but I guess if you stick with that long enough, it escalates and I ended up doing it for about 15 years.”

Things started to “spiral out of control” and resulted in a four-month stint in two of Australia’s most notorious jails: Long Bay Prison and Parklea.

Andrew Hamilton spent four months in two of Australia's most notorious prisons for drug dealing. Now, he's helping change lives through comedy.

It was there that he began to focus on writing jokes and crafting comedy, testing his material with his cellmates while trying to figure out what went wrong and how he could improve himself.

“I’d lost my restaurant, I’d lost my fiancée, I’d lost my dogs, and my friends had all bailed on me. You have a moment to be like, well, this is all a mess, and what could I do differently? Really, the only answer in my head was stand-up comedy.”

He says “taking the p***” out of his own “dumb mistakes and stupid life” was somewhat cathartic.

“To just be able to share that anger in a way where I made it funny, and then to share that with other people and then laugh, it was something that really lightened the burden.

“I think there’s something about that, and taking ownership of my mistakes and making jokes about it, tlly resonated with people.”

Hamilton made himself a promise that, when he got out of jail, he’d start shows. In his first year of stand-up, he did about 260 gigs around Sydney.

Not long after, he was nominated for Best Newcomer at the Melbourne International Comedy Festival in 2023 and had amassed a big online following for his stand-up sets.

“I think I also had, then, a combination between my own sense of humour and something interesting to talk about, which helped me to get some early wins on the board and go viral a few times and start to figure out what works and what doesn’t.”

Andrew Hamilton's addiction to using and selling drugs spiralled out of control. Today, he's finding solace in comedy. Photo / Wolter Peeters

On the reality of prison life, he recalls there was a lot of heavy drug use and moments of extreme violence: “You just see a trail of blood and that kind of stuff.”

But many of the more disturbing moments he witnessed came from seeing “broken men” - the people he now tries to help.

“I don’t think I really came across anyone that I would say was evil in jail, just a lot of guys that have made bad mistakes, a lot of it driven by alcohol and drugs, particularly methamphetamine.

“I think that there’s just a lot of guys in there that, with the right support network and the right opportunities, could rehabilitate themselves. That’s how I try and use my comedy, to show people that not everyone goes to prison as evil and that people can change their lives after it.”

He credits his family for taking him to his early gigs, and his supporters for helping him to turn the tables and forge his career.

“I thought that [Mum and Dad] were going to think it was crazy that I wanted to get on stage and start telling everyone about my drug dealing and getting arrested, but I think they really understood that it was something that I felt drawn to do.

“And as much as I focus on the fact that a lot of friends did bail on me, there are also people that you never expected to be there for you come out of the woodwork.”

With New Zealand immigration clearance sorted and a packed touring schedule, Hamilton says he’s ready to see how Kiwi audiences react to him in person after seeing him only on screens.

“The cool thing about the show is that, among all the drug dealing and jail jokes, there is a sincere part at the end where I talk about the importance of comedy for me, and how I think the laughter can really save a life.”

He also has some sage advice for those struggling with direction in their lives.

“If someone has a passion they want to turn into a real job, then they have to treat it like it already is.”

Andrew Hamilton: Jokes About the Time I Went to Prison

Wednesday, June 11: Whatawhata, The Backyard Gastropub

Thursday, June 12: Auckland, The Tuning Fork

Friday, June 13: Tauranga, 16th Avenue Theatre

Saturday, June 14: Petone, Abandoned Taproom

Sunday, June 15: Christchurch, Space Academy

Tickets are available at alist.com.au.

Mitchell Hageman joined the Herald’s entertainment and lifestyle team in 2024. He previously worked as a multimedia journalist for Hawke’s Bay Today.