The night before Guy Montgomery talks to the Listener, he’s on 7 Days, a show he first appeared on in 2014, having been given a slot as that year’s Billy T Award winner for up-and-coming comedians. He says his 10-year anniversary came up in conversation backstage. “I remember watching 7 Days before I even knew I could do stand-up or that it was a career path and thinking, ‘I reckon I’d be good on that.’ I was saying that to Dai [Henwood] in the green room this week, and he was just laughing at me.”
Montgomery’s first appearance back then was okay, he thought. His second not long afterwards “didn’t go as well, but it wasn’t a disaster”. Still, the show didn’t have him back for five years for some reason. “I remember being really frustrated, because as far as opportunity in New Zealand comedy goes, that was the golden goose.”
But he’s made up for it since. These days, 7 Days possibly needs him more than he needs it. And just as Australia is grabbing our nurses and police, it seems to want to give Montgomery gainful employment.
Here, when 7 Days finishes for the year on Three this month, into its slot will go the second season of Guy Montgomery’s Guy Mont-Spelling Bee, the show he started in the pandemic-lockdown Zoom era with comedy mates before he took it to the stages of Auckland and Melbourne, and soon Edinburgh.
In the TV show, Montgomery is the quizmaster asking for correct spellings and asking lateral-minded questions designed to amusingly aggravate the comedian contestants. Not only has it got another go on local telly, but also the Australian Broadcasting Corporation commissioned Montgomery and NZ producers Kevin & Co to make a version for Oz. With Montgomery as the host, the ABC iteration, with guests including Tim Minchin, debuts in prime time on August 14.
It’s the first time a Kiwi comedy panel format has been exported. In a world where the likes of Taskmaster is made in a dozen countries, Australia doesn’t have to be its only destination. “It would be phenomenal to me if Spelling Bee reached beyond a show I was hosting in Australasia. In America, I don’t think there’s even a realm of possibility in which I would be successful enough to host the show and so I’d love the idea of John Mulaney’s Guy Mont-Spelling Bee … but we’ve made a second season in New Zealand and we’ve made a version of the show in Australia. You want to enjoy that without getting in your own way of being like, ‘Yes! Now the world!’”
Today, Montgomery is on Zoom from the home he shares with partner, actress and film-maker Chelsie Preston-Crayford and her daughter Olive – they, and his stepfatherhood have featured in his stand-up monologues, providing self-deprecating moments among the absurdist, observational stuff that has become his trademark. So, he’s not the only adult in the household whose career involves gigs away from home.
“When you’re a freelancer in the creative arts, it’s very difficult to say no to any job. So, you just have to hope that when you’re both saying yes, you can make whatever it is work and the timing’s right that you’re not both totally absent from each other. It’s a beautiful dance and you don’t get to choose the music.”
Montgomery is off to the UK imminently for four stand-up shows in London (already sold out) before a week at the Edinburgh Fringe, which he finishes with two nights of Spelling Bee live on stage. Its guests will include 2018 Fringe winner Rose Matafeo. Having been involved in its online infancy, beaming in from London, she is also one of the contestants on the new NZ series of Spelling Bee, which was recorded last November.
Montgomery and Matafeo go back. They were both part of Snort, the regular improv night and talent incubator at Auckland’s Basement Theatre in the early 2010s and on the short-lived youth channel TVNZ U around the same time. They double billed at the Melbourne International Comedy Festival, then Edinburgh in 2015, when she stayed on in the UK to rise to prominence with her sitcom Starstruck.
“She’s a great friend and a huge source of inspiration to see what she’s achieved and how she’s managed to stay true to her sensibilities and vision, and also how she’s managed to take such immense success in her stride.
“In terms of having a more successful and famous friend to talk to, and try to shrink your problems down … it’s quite fantastic.”
Montgomery was last at the Fringe in 2019, and this time will be one of a dozen or so Kiwi acts on the massive bill. If that helps get him a foothold in the UK, he’s already well on his way to being World Famous in Australia, even before Spelling Bee goes to air.
In past years, he’s been a regular face on Have You Been Paying Attention?, the original of the Aussie panel show that had a four-season TVNZ iteration. It helped sell tickets.
“I could see there were more people coming to watch me and the demographic shift from people who look like me to people who look like my parents’ friends.”
Montgomery won the top show award at last year’s Sydney Comedy Festival. He co-hosted this year’s Melbourne festival opening night gala in April. (“It is a sad indictment on the state of Australian comedy when they have to ask a New Zealander to host one of their most prestigious shows,” he joked.) His solo show shifted from the smaller theatres of past years to the 2000-capacity main space at the Melbourne Town Hall.
“I can’t pinpoint exactly how it happened, but it appears – well, not even appears, I’m experiencing it – there is an enthusiasm for me in Australia, which I’m very happy about. It’s awesome.”
However, he does admit the elevation into a brighter spotlight and a run of the biggest shows of his career caused him enough anxiety to need a talk with a psychologist who he has occasional chats with.
“There was a period where I was staring down the barrel of all these firsts and really feeling the audience was going to be sceptical of whether I deserved to be in a room that big. My peers were probably looking at me thinking, ‘Why is it happening to him? He’s not that good.’ But you just have to remember that no one really cares about you, how small your imprint is, how uninteresting your anxiety is to the world – and if you just let go, it gives you such a relief.”
If he’s in demand in parts foreign, that’s also where Montgomery started. Having grown up in Christchurch, wearing the blazer of Christ’s College and completing a BA in theatre, film and media at Victoria University of Wellington, a post-grad aimless period of jobs led to a decision – he was funny, so let’s try comedy.
He went to Canada and spent a year doing open mic nights in Montreal and Toronto, figuring he could grow up in public away from the embarrassments of a home town crowd. Plus, Flight of the Conchords had just broken big.
“As a New Zealander, performing almost gave you a small window of opportunity at the start, where the association with the New Zealand accent was those guys, and so they thought this might be funny …” And that’s why back then, he says, he sounded a lot like Rhys Darby.
These days, Montgomery’s voice and cadence are lower and slower and he revels in a kind of mock formality that likes to chew through elaborate phrasing. He can sound like he comes from an earlier generation of comedians. He’s worked on slowing things down, getting the audience to listen in. “It’s almost just control of cadence where, if I can just say the sentence and get a laugh, I can create chaos with what comes after.”
That sense of delivery meant when Montgomery won the prize for best show at last year’s NZ Comedy Festival and that the trophy was the Fred Award – named for John Clarke’s Fred Dagg character – it was kind of apt. He didn’t find the works of Clarke until he’d already started in comedy. “Once I found out about it, I was going through all of his stuff and just thinking, it’s unbelievable what he does.”
His father introduced him to Peter Cook and Spike Milligan, two of Clarke’s biggest influences, as well as Monty Python, at an impressionable age. That all got mixed with a love for Friends, the Adam Sandler movie Happy Gilmore, the early stand-up of Ricky Gervais and the deadpan delivery of Canadian comic Norm Macdonald.
“When you start, you’re writing your own jokes, but you’re copying everyone you love and so you overlay all these inspirations and these voices until you either keep going long enough, or your own voice emerges through the sort of the pastiche of everything.”
By that definition, Montgomery says it wasn’t until 2021 – in a performance at the NZ Comedy Festival Gala – that he felt he was “really, properly funny”.
“I really could just feel the entirety of the set. And I knew that the laughs built on top of each other, and I remember coming off stage and thinking, ‘That’s what I want it to feel like,’ which was unique and different from coming off stage previously and being like, ‘Shit, that was a good gig.’ It was ‘that’s how I want to feel’.”
And despite two TV Spelling Bees putting his name in lights – or at least, a large retro font to match his suit – stand-up remains Montgomery’s priority.
Some of that is just practical, given the precarious state of broadcast media. Some of that is having found his voice, wanting to know what it might say next.
“I would love to continue to improve as a stand-up comedian. I think I’m the best I’ve been, but I don’t think I’m as good as I can be.
“I will also say, in the face of the changing winds of television and media, I feel kind of insulated more from the crumbling traditional media model.
“When I have a live stand-up show, I can tour and have a direct relationship to an audience that way. I would feel more scared of what’s happening at [Three owner] Warner Bros Discovery if I didn’t have stand-up.
“I feel more protected against whether or not someone wants you in their show, or whether people have to say yes for you to make a show.”
Guy Montgomery’s Guy Mont-Spelling Bee starts on Thursday, August 22, 7pm, on Three and ThreeNow.
