Blending family into comedy
Comedian Guy Montgomery brings a subject close to his heart into his material, writes
There’s been a mix up. When organising a location to photograph comedian Guy Montgomery, The Hollywood in Avondale replies with an easy ‘yes’, he’s got a bunch of T-shirts to pick up from them anyway.
So when I arrive at the theatre and spot him sitting tall on the front steps, mug of coffee in hand, I open by saying I’m glad our photoshoot could facilitate the safe return of his merchandise. The conversable Montgomery says he’s “been hearing a lot about these T-shirts” but admits with a laugh he has no memory of them.
A few minutes later the venue manager arrives, clearing up the confusion - she’d misread our email and thought we were profiling Guy Williams. It’s an understandable muddle, given their shared name and profession, but at the moment Montgomery is the Guy in New Zealand comedy that everyone’s talking about.
The year 2023 could be considered something of a dream season for the 35-year-old comedian. He scooped best show awards at both the New Zealand International and Sydney Comedy Festivals, and debuted his now cult favourite TV show Guy Montgomery's Guy Mont-Spelling Bee on Three. His hosting of the comedically unconventional gameshow earned him a nomination for TV Personality of the Year at the NZ Television Awards.
The fortuitous spell seems to have carried over into the new year. When he starts the national tour of his new standup show 50,000,000 Guy Fans Can’t Be Wrong at the Wellington Opera House on May 11, he’ll be fresh from an extended run across Australia. Demand saw extra shows added in Adelaide, Canberra, Sydney,
Perth and the upcoming Brisbane dates. The second half of his month-long run at the Melbourne International Comedy Festival was upgraded to the larger main room of the town hall.
“The Melbourne festival is kind of the apex of southern hemisphere comedy festivals, that's where most of the energy and thought goes,” he tells me as we settle down at a table in the courtyard to chat. That’s where his mind’s turned now.
“My immediate dream is to get this show up to a standard I'm happy with where I don't have to worry about how it's going to go on the night. I can enjoy the experience of coming out and knowing it’s funny.”
Lauren Whitney, chief executive of the NZ International Comedy Festival, says the wide-recognition Montgomery’s getting is well-earned and also a sign of things to come. “He’s where comedy is at.
“He’s been achieving all sorts of things and he’s such a hard worker, an innovative thinker and he’s changed the game so many times already with podcasting Guy Montgomery’s Guy Mont-Spelling Bee, we haven’t seen everything yet.”
While appreciating the accolades, and acknowledging they help with ticket sales, Montgomery tries not to think about them too granularly, or at all really. “The healthy thing to do is to block out anything to do with awards,” he tells me.
This approach has worked for Montgomery, Monty to his friends, so far. When he found out he’d won the top prize at the Sydney Comedy Festival he was staying at a friend's place in Wellington. “I got an email while we were playing backgammon,” he recalls. “I thought ‘this is perfect’. I didn't have any stress about it, was just delivered a nice piece of news.”
Last year in an episode of the Wilosophy podcast Montgomery told host Wil Anderson that he landed in comedy because “I thought I wouldn’t have to work, because I was already funny”.
The middle of three children, flanked on either side by sisters, Montgomery was born in Wellington but his father’s career in finance saw the family move “to Sydney, then back to Wellington and then to Christchurch, all before memories”. He does have memories of childhood around comedy though, listening to Monty Python on CD during family road trips, his mum’s ‘big energy’ and Dad’s ‘dry’ humour.
Even so, comedy was never the plan, or the goal. Truth be told he didn’t really have one. “Christchurch is somewhat traditional so it was never advertised to me that these pathways were available, that you could become a comedian,” he told Anderson.
Instead he found his way back to Wellington, to Victoria University, getting a Bachelor of Arts in theatre, film and media without really exerting himself, happy to, in his words “shit it out on the day” because he had no intention of using any of this in real life. His priority was socialising. It wasn’t until his friends started to make tracks in their own careers that Montgomery took stock of where he was
headed. He landed on comedy after interrogating what he liked doing the best and what he seemed to be the best at doing; the answer was being funny.
But transitioning from being the funny guy in your friend group to being professionally comical isn’t as simple as getting a mic in hand. He joked on stage last year that “I was born, no obstacles were put in front of me, and now I'm here”, but talking to him about his approach I'm struck that he’s a hard worker and deep thinker. His warm and natural onstage delivery sometimes belies his earnestness.
When Montgomery decided to actually make a go of stand-up he uprooted himself to Canada - Montreal, then Toronto - seeking to better himself and his delivery away from people that knew him.
“I'd done maybe two or three open mics here before I left but I hadn’t taken them seriously,” says Montgomery. “I had a funny instinct but I wasn’t really good, I was going up half cut, I had no control. I went away, came back and I'd been working really hard. I wanted to re-introduce myself. I took that seriously.”
He still grapples with being green, but he’s bringing it to the stage now, putting it under the spotlight. “At the show's core is me feeling like I don’t have a hobby,” he explains.
“I think a big barrier to trade in me getting a hobby is that I don’t like not being good at something. The whole thing with having a hobby is you’re bad at it and then you improve. The pleasure is meant to be in the doing, not in the being good.”
Many of Montgomery’s outwardly goofy endeavours do delight in aspects of messy raw creativity. Take The Worst Idea of All Time, his decade-long podcast with comedian Tim Batt, that saw the pair watch a series of movies of debatable quality over and over again, starting with Grown Ups 2 and moving on to the Sex and the City and The Fast and the Furious franchises.
One of his earliest steady TV jobs was Fail Army for Three, a syndicated America’s Funniest Home Video style clip show that contractually couldn’t be re-edited, which he presented alongside Joseph Moore who he now writes Spelling Bee with. The pair drastically reframed the narrative using voice overs and pieces to camera that preceded the packages.
Montgomery says all these seeming artistic indulgences are actually examples of restrictions being a way to force creativity. “It’s all feeding towards the same thing you know, strengthening the muscle and discipline, the writing or the performing.
“To book a ticket with the discretionary spending that people have now, it's not an easy ‘yep’. You have to plan part of your month around this event and if you have children it's not just the ticket, it's the hours around it. That's why the show has to be good though.”
His own time is more precious now too. Previously he’d do multiple nights at medium sized venues but he’s now doing one-off shows in bigger venues. Prolonged stretches away now take him away from his partner, actor Chelsie Preston Crayford and stepdaughter Olive, 8.
“When I was younger I'd want to spend as long as I could [away], to see my friends and hang out, that's still really fun to do but the value on that is now lower than the value of actually just getting to be at home.”
“Every second family is a blended family but there's no public discourse about it, no representation in movies or TV, it's never been in stand-up that I've seen which is kind of why I wanted to talk about it.” Guy Montgomery
Being a step-parent was not the plan either. As he said on stage in last year's show: “You fall in love with who you fall in love with and if they have children or a family you absorb them into whatever version of a family you choose. For me that's being a step-parent. I say this with total sincerity: It's the single
most rewarding part of my life. I love it so much but I think the hardest part of being a step-parent is finding a family to break up. I kid, I kid - if you find the right family they would have done it themselves.”
The show, My Brain Is Blowing Me Crazy, named after an idiom coined by Olive, was about as personal as Montgomery’s stand-up has been.
“I was trying to be silly and funny at first when developing it, but the last third I was trying to stuff it with jokes and it became this reflection on the relationship with Chelsie and Olive.”
He says in the show: “Every second family is a blended family but there's no public discourse about it, no representation in movies or TV, it's never been in stand-up that I've seen which is kind of why I wanted to talk about it.”
The show this year is less personal, not necessarily by design, but instead the result of following his creative nose. He has no qualms about including more of his life in his comedy and knows the people in his life won’t hold back on their honest feedback. “If I say to Chelsie I'm thinking of a joke about this or that she’ll always say ‘it's hack’, which I love. Even if it's funny.”
When he is away from home, Montgomery is deliberately investing time and energy in the Australian market. The lucky country offers an accessible extension to the opportunity ceilings one rubs up against in a smaller market like New Zealand.
An Australian version of Spelling Bee, fronted by Montgomery, was commissioned by the ABC this month, a huge step for the show which was originally conceived as a way to entertain his friends during lockdown. Early episodes were streamed live on YouTube and drew on his global network of comedian friends, Tom Sainsbury, Rose Matafeo and The Bear star Ayo Edebiri all made appearances. The comedy camaraderie continued when the show got picked up by Three.
“It sets them up to be funny in their own voice and sets them up for success,”says Whitney. “He’s there to hold them in that space. He’s providing opportunities and programming people not just with big names but people getting their first TV slots.”
Abby Howells, who last year won The Billy T Award celebrating the growth of fresh talent in the New Zealand comedy industry the same night Montgomery won The Fred award for best show, says he sets an example for the local comedy scene in more ways than one.
“He works hard, he is constantly challenging himself to be better, he takes risks. And he is also really friendly to everyone and kind, he gives everyone the time of day.”
Howells recalls the first time they met in 2021. “I had come from Dunedin to perform my solo show for the first time in Auckland… Guy seemed so excited for me. He immediately bought tickets to see my show, right there in the bar. He came to see it the next night, sat in the front row and then went to work hyping me up online, trying to get more people to come to see my show.”
The support doesn’t stop there. “He’s consoled me after a break up, he’s encouraged me when I am down, I think he is a real pillar of strength for a lot of people in comedy.”
His personal and professional lives look different to when he started in comedy but more than a decade in, and at the top of his game, Montgomery’s still finding joy in the things he relished when starting out.
“I like that it's just language. I like that you just talk and you can create something for people… I like that you can do it with nothing in your pockets. It’s amazing, kind of this platonic ideal of what a job can be.”