Guy Mont-Spelling Bee host Guy Montgomery reflects on his weird and wonderful comedy journey and influences ahead of his Auckland stand-up show this August. Video / Cameron Pitney
It’s not hard to spell out that Guy Mont-Spelling Bee host Guy Montgomery is at the top of his comedy game right now. Through golf metaphors and golden nuggets of insight, he tells Mitchell Hageman about how family, friends, and failures helped navigate the often-fickle business of comedy.
“Do youplay golf?” Guy Montgomery asks me, as we segue from discussing the ebbs and flows of the intricate career that is comedy.
I tell him I do play, albeit not very well.
“Don’t you think the sooner you go out and play your first round, the sooner you can look forward to your second round and feel slightly better?” the 36-year-old game show host and comedian extraordinaire says, using the game as somewhat of a metaphor for his comedy career.
“And then at some point, it becomes addictive because you think ‘I’m getting better at this’, and you get to experience, you know, not necessarily mastery in that you are the best, but mastery to the standard that you’re capable of at that time, and that’s what’s satisfying.”
It’s an insightful way to look at a career that at times can be rather brutal on your confidence.
From his days doing open mic nights in Canadian clubs to hosting one of Australia’s most successful and insane quiz shows (Guy Montgomery’s Guy Mont-Spelling Bee), he’s one of Aotearoa’s most successful international comedians..
Guy Montgomery is a comedian and the host of Guy Montgomery's Guy Mont-Spelling Bee. Photo / Cameron Pitney.
Now also a regular fixture on the Australasian stand-up circuit, Montgomery admits there are still things he’s learning about himself as an artist and a human.
Starting his comedy journey doing stand-up in Canada was helpful, in his words, “to build an openness to failing away from people I knew”.
“I think doing [stand-up] in a place where I didn’t know anyone absolutely diminished the opportunity for embarrassment, and so probably emboldened me,” he says.
“There was a greater willingness for me to just go and be bad at something. It’s something that, oddly enough, I still feel I struggle with in ordinary life,” he says.
Montgomery’s stage exploits have since garnered rave reviews and even earned him both a Billy T and Fred Award.
“When you first do stand-up, you just do it sort of because you love it. You do it because you think you might be funny and you want to see what it feels like to stand up there and get a laugh,” he says.
“The actual practice of figuring out stand-up material and putting a show together doesn’t change from when you first are putting together a five-minute set to when you’re 15 years in and putting together an hour-long show.”
Guy Montgomery credits his fellow Kiwi comedians for helping him thrive. Photo / Andi Crown
Between his packed schedule of touring and TV, there’s also another string to Montgomery’s bow of life that’s close to his heart. For the last seven years, he’s taken on the role of stepfather to his partner Chelsie Preston Crayford’s (Underbelly: Razor, A Remarkable Place To Die) young daughter.
“I don’t know that I’m still taking it on so much as it’s part of the fabric of my life. I love it,” he says,
“It’s incredible, and it’s a funny thing because it’s not something that you necessarily expect for yourself, and not something that you necessarily aspire towards – it’s something that happens based on who you fall in love with, and it’s been amazing.”
Guy Montgomery and partner Chelsie Preston Crayford attend the New Zealand Television Awards 2023. Photo / Getty
With both Montgomery and Preston Crayford being involved in the entertainment industry, they understood the expectations of each other’s work-life balance.
“You do have to balance who’s doing what at what times, and exercise as much agency as you do over both of your calendars,” Montgomery says.
“It’s probably been really beneficial for our communication because there’s always open communication about what we’re both doing professionally and then that bleeds into your free time as well.”
There’s also a bit of healthy competition on the cards. Montgomery is up for the Graham Kennedy Award for Best Newcomer at the Logies in Australia, an award Preston Crayford won for her role in Underbelly.
“It’s kind of funny, I guess, like she has an AACTA award as well, which is the other big television and film awards night, and I got nominated for two AACTA awards this year and lost them both. This represents the last opportunity to even come close to squaring the ledger at home.”
He jokes that he’s taken Preston Crayford’s trophy for “a walk around the house” to visualise what it would be like.
“But it’s a popular vote, so you can tell people to vote, but you ultimately have limited agency on how it’s going to go.”
While a globetrotting Montgomery’s career has allowed him to perform in many iconic international venues, he says he’s excited to return home next month for a special Kiwi show in Auckland to end his tour.
He’s also grateful to the Kiwi comedy scene and his fellow comedians like podcaster Tim Batt and Two Hearts stalwart Joseph Moore, as well as those who worked on the long-running Basement theatre improv night SNORT in Auckland.
“I’m very lucky to have come of age at a time when SNORT materialised in the Basement, and to find that community with all of us being able to collaborate and push each other forward and support each other.”
And his advice to those wanting to get into his line of work is simple: just start trying.
“I would do as many stand-up comedy gigs as I could, any open mic I could, and perform in any space that would have me. I think that remains probably the most powerful way of improving and getting better,” he says, returning to his golf analogy.
“If you’re thinking about it, but it’s too embarrassing because you’re going to be bad, the reality is the sooner you get through being bad, the sooner you get to enjoy being good. You just have to start.”
