The Cantabrian, who has accrued a Billy T Award and a Fred Award in recent years, only considered comedy at 22 after watching his friends head into jobs from university and realising no other career path held as much long-term appeal.
In an interview with Newstalk ZB’s Real Life with John Cowan that aired on Sunday night, Montgomery spoke in detail about his meteoric rise from confused graduate to beloved comic, podcaster and TV personality in the space of a decade.
“I was fresh out of university, working in hospitality and doing odd jobs in media,” he told Cowan.
“There was nothing that had taken me. I thought I might work in advertising or be a teacher, but neither of these were callings – they were just more permanent ideas than what I was currently doing.”
Montgomery knew he was funny – he’d always had an innate ability to make people laugh – but the thought of performing stand-up to a local crowd initially felt too uncomfortable.
“A lot of my identity was built around the idea of being funny, and I knew to try stand-up, I would have to live through not being funny – because when you first start, you’re bad,” he explained.
“For my identity to be enmeshed in being funny, it was kind of a block for me. I guess it was ego, but I couldn’t bear the idea of getting up on stage at an open mic in front of my friends, who I’m so funny to in day-to-day conversation, and not being good at it.”
It was at this point, Montgomery told Cowan, that he decided to move to Canada to pursue a stand-up career – a decision that would change the course of his life forever.
“I went to Canada because it’s easy to get a visa since it’s part of the Commonwealth… I didn’t do a huge amount of research, I just got the visa and saved the money and moved to Montreal,” he said.
Guy Montgomery averaged more than one gig a day over a year in Toronto.
“Then I went to Toronto for a week to visit, and got up on stage every night. There was an open mic every night, and I thought, ‘this is where I need to be’. And so I went back to Montreal, packed my bag, caught a bus to Toronto and found a place.”
Montgomery made the most of his opportunities to hone his craft in Toronto, averaging more than a gig a day over the following year.
“[In New Zealand], I didn’t have the self-discipline to want to stop hanging out with my friends,” he said.
“I had the option to sit around and play cards and have a laugh, or go out to an open mic where I didn’t know anyone and be bad at something. The easy choice was to just keep hanging out with my friends.”
But in Canada it was “the opposite”.
“I got incredibly data-driven. I did ten shows a week – that was the minimum I set myself – with the logic being you cannot not improve… it was like three years of New Zealand gigs condensed into one.
“I had no friends in Toronto, I don’t know anyone. And so the people I met at the open mics, these other comedians who were starting out, became my community.
Guy Montgomery will be touring New Zealand this year with his new show Over 50,000,000 Guy Fans Can’t Be Wrong. Photo / TVNZ
“It wasn’t a choice between hanging out with my friends or going to the open mic; going to the open mic was hanging out with my friends. It was an amazing experience, it was such an incredible year, and I do think it’s probably [made me].”
Montgomery, who will be touring Australia and New Zealand this year with his new show Over 50,000,000 Guy Fans Can’t Be Wrong, says he’s at his best as a stand-up comic when he “can be totally relaxed”.
“Because I didn’t want to not be funny in front of my friends [when I started out], my first stated goal was that I wanted to feel like I’m talking to an entire audience of my friends, with the same sort of relaxed confidence.
“That’s the dream. It sounds ridiculous, but all of this, I couldn’t have asked for any more than what I’ve got.”
Real Life is a weekly interview show where John Cowan speaks with prominent guests about their life, upbringing, and the way they see the world. Tune in Sundays from 7:30pm on Newstalk ZB or listen to the latest full interview here.
