Guy Montgomery was an extremely annoying child. Each night at dinner, he would attempt to get his younger sister to laugh so hard she snorted out her food. One evening, when his parents had friends over, he spent the whole meal pretending to be a South African exchange student. “My mum was like, ‘He’s not, he’s my son,’” Montgomery says. “She was chasing me around the table, laughing, and I ran to my bedroom. When she came in later I was asleep.”
He once read a joke book out loud all the way from Blenheim to Christchurch, a four-hour trip, telling zingers such as this one: “How do you keep an ugly monster in suspense?”
“How?” I ask.
“I’ll tell you tomorrow,” the now 36-year-old Montgomery says, and I don’t know if I’m grinning because it’s kind of funny or because he’s so obviously delighted.
Needling loved ones to the point where they are frustrated but laughing – “so that the annoyance has no power” – is a comedic styling that has propelled the New Zealand comedian’s career and powered his popular game show Guy Montgomery’s Guy Mont Spelling Bee, kicking off its second Australian season this week on ABC. The irreverent and absurd show contains various segments that give guests – including Rove McManus, Hannah Gadsby, Hamish Blake and Denise Scott – the chance to tell jokes while failing abysmally at spelling tasks that range from basic to impossible. Montgomery reigns over the resulting chaos like a kind of encyclopedic svengali. “I describe myself as the protagonist and antagonist of the show,” Montgomery says. “It’s designed to be enjoyable to watch and irritating to take part in.”
Raised in Christchurch, Montgomery dipped into standup aged 22 when he was “idling around” post-bachelor’s degree. During the day, he worked as a mascot at agricultural shows, with stints as a popsicle, an orange bull and a peach-flavoured Bundaberg; at night he hit up local comedy clubs. He was already funny by then, he tells me, devoid of the self-effacement Kiwis are known for. “I was funny basically the whole time,” he says, deadpan. “I just didn’t take it seriously. I got drunk and told a story and it went well, and I did the same thing again and it didn’t. I had no control.”
He needed to get better, but he didn’t want people he knew watching, so he went to Canada – randomly chosen for ease of visa access – and hit the standup circuit in Toronto while working in hospitality, tallying his gigs in the same notebook he wrote his jokes in. “It was kind of an extreme form of self-discipline,” he says.
That’s when he started to learn how to get people to laugh. “When I first started I was just copying Rhys Darby; they were my jokes, but I was in his cadence, and you overlay all of these influences until your own voice emerges,” he says. “You’re not being funny on your terms. You don’t necessarily believe in what you’re saying because you’re just chasing the ability to make people laugh, and that’s the addictive feeling. Over time, it goes from saying something you hope the audience will laugh at to saying something you know they’ll laugh at.”
Returning to New Zealand in 2014, he won the Billy T award for the country’s top emerging standup comedian. This led to a series of TV hosting gigs, during which he met and vibed with local comedian Tim Batt. Their podcast together, The Worst Idea of All Time, gave an indication of the kind of cult following Montgomery’s comedy inspires, with 350 people filling a New York theatre in 2016 to watch him and Batt talk about Sex and the City 2, a film they had watched every week for a year.
Montgomery conceived The Guy Mont Spelling Bee in Auckland during Covid lockdown in 2020, inviting comedian friends and acquaintances – including Ayo Edebiri and Rose Matafeo – to join in on Zoom and stream the results on YouTube. “I was always intrigued with the idea of spelling bees – there’s all the pomp and pageantry,” he says. “You’d watch the moderators reading out these quite ornate sentences just to get the word in there, and that’s a pre-existing joke format.”
It spiralled out to a stage show, and in 2023 it was picked up by New Zealand’s channel Three, after which Montgomery and co-writer Joseph Moore pitched it to the ABC with comedian Aaron Chen attached as co-host. Montgomery says having two seasons of the New Zealand show under their belt was an advantage, in that producers have mostly left them alone. “Because it arrived fully formed, it means it’s an accurate and total expression of a comedic instinct.” Some returning comedians are invited to help brainstorm new games for the show, but Montgomery and Moore are still the lead writers.
The recipe has proven a hit, generating rave reviews and lengthy Reddit threads. “When people fall in love with the comedy format like this, the fandom is quite intense,” Montgomery says.
Fans often speculate how much work must go into the show’s preparation. “You do drive yourself crazy writing this many jokes,” Montgomery admits. “But also I love that … I want it to feel like it’s brimming or overstuffed, and for people to want to know what the joke [was] for a certain word that we didn’t get to say.”
The handmade, retro feeling of the set is also intentional, to spark nostalgia and a childlike desire to walk in and touch everything. “There’s a comfort food quality to these shows,” Montgomery says. “They don’t reflect any of the crazy stuff that’s happening, it’s pure escapism.”
This might also account for the intergenerational audience, with kids coming to the show with their grandparents. “I used to know what my audience demographic looked like but in Australia now it just looks like everyone,” he says.
Staff in this Wellington cafe recognise Montgomery because of his partner, the New Zealand actor Chelsie Preston Crayford, who was filming nearby last year. In Australia, people now stop him on the street; audiences for his standup shows have tripled. “I’m experiencing success,” he says. “In New Zealand, no one knows or cares.”
Initially, that popularity brought on anxiety and a kind of guilt, which he has talked to his therapist about. “She said: ‘You’re looking over the ledge of what would happen if it went wrong and you think you’re going to fall all the way down, but you’ve got all these years of practice and experience,” he says.
These days, he exudes the quiet confidence of someone who has found not only their calling but their gift: “What I’m really good at, the means I have of helping the masses, is by being funny.”
Season two of Guy Montgomery’s Guy Mont Spelling Bee premieres on ABC TV and iView on 4 June. Guy Montgomery is touring Australia through June and July.
