The drug dealer turned stand-up comic who’s now high on laughter

Just two years ago, Andrew Hamilton had an excellent reason not to crack jokes – he was in a high-security jail for selling magic mushrooms and LSD.

“In a lot of prison wings, you don’t want to draw attention to yourself,” he explains.

Former drug dealer Andrew Hamilton has served time in prison and is now a comedian.Credit: Wolter Peeters

“You’re trying to make yourself as invisible as possible. It can go wrong very quickly if you’re a smart arse to the wrong person.”

Now, he’s hitting comedy stages with his show Jokes About the Time I Went to Prison, which saw him nominated for the Best Newcomer Award at the Melbourne International Comedy Festival.

In the show, Hamilton shares his prison food reviews (a hit on TikTok) and tells stories about his time behind bars: including when corrective services officers asked him both if he was contemplating suicide and whether he wanted to buy a television for his cell.

Comic Andrew Hamilton in Sydney.Credit: Wolter Peeters

Jokes About the Time I Went to Prison also candidly touches on some of Hamilton’s life leading up to a police raid of his home back in June 2021.

Despite an apparently flourishing career - he worked in public relations and also owned a high-profile pizza shop in Potts Point - he experienced suicidal thoughts, became addicted to gambling and illicit substances, and eventually started to deal drugs to support his habit.

He’d always wanted to try his luck at stand-up comedy but had never found the nerve.

Now, he’s making up for lost time, having progressed quickly from open mic nights to being a NSW Raw Comedy finalist and winning acclaim for his debut festival hour.

“It has been a quick development, but I guess I had so much I wanted to get out, both from my prison experience but also from my mess of a life in the years prior to that. I felt like I had some real venom and passion in what I wanted to talk about right now,” he says.

Hamilton was granted bail and released from jail on the condition he lived with his parents. He also had to be accompanied by one of them while out at night, so his mother would go with him to his open mic night performances.

He would ask event organisers to perform early in the night because he had a curfew of 10pm.

Still, his first time on stage was a revelation.

“I spent nights and nights memorising my set. I didn’t really perform it; I just said the words. But it felt so, so good to get a laugh. As soon as you hear those first laughs, a wash of relief comes over you.”

He soon found kindred spirits in the scene.

“There are guys you’ll see at every single open mic night. If you get up every single night of the week trying to make strangers laugh, and getting either zero or five dollars for it, you obviously have something in you that’s driving you to do that … I think other comics see that in each other.

“I’d lost a lot of friends because of what happened, so it was so much fun to start telling jokes and meet this warm, welcoming comedy community in Sydney.”

Having survived the extreme circumstances of jail, Hamilton says he’s not afraid of bombing on stage. Instead, his experiences have motivated him to put all of his energy into stand-up.

‘I was at such a low point I felt like I had nothing else to lose.’

Convicted drug dealer Andrew Hamilton on why he turned to stand-up comedy

“I was at such a low point I felt like I had nothing else to lose. Maybe it made me a bit fearless. I don’t think I ever would have done stand-up comedy if I didn’t lose everything first.”

Far from being the grim hour you may anticipate, Hamilton’s show is surprisingly upbeat.

“I’ve always been an optimist, and that helped my situation. Also, because of the depressing environment you’re in, whenever something funny happened, it was twice as funny … Laughter is a very transportive thing.”

Hamilton is particularly proud of the work’s closing stretch, where he reflects on the role comedy has played in changing his fortunes.

“I wanted us to think for a moment: Why do we perform comedy? Why do people come and see comedy? I truly believe it’s because having a laugh is hugely therapeutic. It can change a life.”

Andrew Hamilton’s ‘Jokes About the Time I Went to Prison’ is at Factory Theatre on May 18, 20 and 21.