Guy Montgomery on making comedy in New Zealand – and why he’s moving to New York

You might know Guy Montgomery from winning the Billy T Award a few years ago, from his smash-hit podcast The Worst Idea of All Time, or from TV3’s Fail Army. Sam Brooks talks to Guy about his career in comedy and what he plans to do in New York.

Sam Brooks: Are you ready to be enthusiastically interviewed?

Guy Montgomery: My friend, I have woken up for this exact moment. I am just setting up my bluetooth speaker so I can soundtrack the interview.

What’s your soundtrack for the conversation?

It’s a playlist I am still making for the month of April but I mostly set it up to listen to this one song called ‘Tezeta’ by Mulatu Astatke. It makes it feel like I’m still asleep although I assure you, I am very much not.

Are you listening to anything?

I’m listening to The Shondes! They’re a Jewish feminist punk-pop band.

I do not know of the Shondes, I will listen to them.

Like five people have heard of them and it makes me feel incredibly superior and exclusive listening to them.

As well it should! They have quite low Spotify numbers.

They’re just waiting for that Jewish feminist punk-pop boom. It’ll be Pitbull, then them.

The Shondes set a very different tone to my man Mulatu. There are too many lyrics to focus on what I’m doing! This is madness. I’m sorry, I’m bailing out.

Now I am back with Mulatu.

So I’ve been trawling some of your interviews, and I realise that I have no idea what you did before you did comedy. So my first proper question: What did you do before you did comedy?

Before I did comedy I went to university in Wellington and worked in hospitality, supermarket promo, just did anything that avoided feeling like real work. Supermarket promo was the big earner, standing at the entrance to a New World encouraging people to try an exciting new range of cheese or whatever.

One summer I did promo for Bundaberg Peach during a big heat wave in Christchurch and you should have seen the roll I got on! The Bundaberg Peach is good to try a shot glass of but certainly no good for a whole bottle – it’s too sweet – but the sample sizes I was giving out were only a shot glass worth.

I could sell out the supermarket’s stock in less than an hour and you get paid for a full shift either way. Truly the halcyon days of supermarket promo.

Why on earth would you give that up for comedy?

I ask myself the same question every night before I walk on stage.

As it turns out, it wasn’t fulfilling on a long term basis.

Guy Montgomery.

So when did you transition into doing comedy?

Well after I finished my ever valuable BA I moved to Auckland and started flirting with media-adjacent work. Still working in a cafe and a restaurant but also angling to do whatever work I could for George FM, occasionally hosting a show with my friend Tim Lambourne who was and is much more established at the station.

Meanwhile all of my friends at university in Auckland were finishing degrees and settling into their ‘adult’ jobs and so all of the free time I’d been trying to hoard during the day by avoiding regular work was no longer as valuable and I realised I didn’t want to be doing three or four odd jobs while everyone grew up around me so I thought about it objectively in terms of ‘what do I like doing the best?’ and ‘what am I the best at doing?’ and the answer to both of those questions was being funny so I thought I’ll try and do that.

This is kind of a vague and wishy-washy question, but what’s important to you in comedy? Both as someone who does it and someone who probably watches a lot of it.

A wishy washy question demands a wishy washy answer and for me it is just being funny. When I watch Netflix or whatever, I would say 90% of the stuff I watch is comedy, that covers a broad spectrum of comedy but I just love the stuff.

That is exactly the answer I deserve for that kind of question.

For my own performance, it is very important that I am enjoying myself and that is something I’ve had to consciously work very hard on lately.

Why’s that?

Because this is my sixth year performing and I feel like the longer you go there will be patches where you plateau and patches when you hit a purple patch in form or achieve some sort of break through.

So for me, the last two years in terms of my stand up I feel like I’ve been plateauing and that marks it hard to enjoy yourself as much so I re-adjusted my focus to go back to why I got into it and what I enjoyed in the first place which was having fun, because I think (for me particularly) if I am enjoying myself there is a high chance the audience will also be enjoying themselves.

And this Melbourne [Comedy Festival] I have been having such a good time making sure I set myself at the start of the show, that everyone in the room is familiar with my energy and knows they are in safe hands and it has made for the most enjoyable run of gigs I’ve done in my life.

I am always afraid of spoiling the magic and sounding like a nerd but when you are in the midst of a month long festival you wind up talking about this stuff so much it kind of becomes unavoidable.

That’s really cool! I’ve never heard someone talk about comedy or performing in that way, but when you word it like that it seems super obvious and it makes complete sense. And I guess for a comedian who is as high energy as you are, it would be incredibly draining to do that, to put that much energy out into the world and the audience for an hour, if you’re not enjoying it.

Exactly! That was exactly the thing, and it is draining for an audience as well because whether or not they consciously or subconsciously know it, they can tell when you aren’t entirely present and then you have friction between you and them.

It’s also about self-care, right? As wanky as that sounds, but you’re your own product and if you’re not enjoying what you’re doing then you need to adjust and stuff.

There is an element of that, I made a very concerted effort this year to focus much, much more on stand up.

Which is why you’re moving to New York, yeah?

What I think can happen in New Zealand is you start doing stand up and you get quite good at doing it and because our industry is so small and overlaps with TV and radio, then you get picked up to work on comedy-adjacent projects which is awesome because the money is better and it is extremely validating but before you know it three years have gone past and stand up is the thing you do on the side rather than the main thing.

For me, I wanted to see if I liked doing it as much as I remembered and if I was as good or capable of getting as good as I wanted to be. And yeah, this is all part of why I am moving to New York because I am still young enough and hungry enough that I won’t mind starting from the bottom again.

And if I don’t measure myself against the biggest market in the world then I will never get to know how good I am or how good I could have become.

Do you know New York very well?

I have been a few times, I spent a month there during summer in 2013 but I am kind of going in cold. I have some non-comedy friends there and a few friends through Twitter and the podcast but it is going to be very interesting. I will, in essence, be starting from the ground up as a stand up.

That’s really exciting, and super cool. I can totally empathise with feeling like you’re getting stuck in your artform. I think NZ is so small and any artistic or creative industry is so small that you can end up at the top, or very close to it, very quickly and then you spend the rest of your life just treading water, which is the least creative thing in the world.

Yes exactly. And that is also what makes NZ so amazing, the opportunities you are afforded so quickly are second to none and this is stuff it takes ten years, twenty years to get to do in larger scenes. But once all of that happens then there is a bit of ‘what’s next?’.

Coming to Melbourne has also been great for that, this is a huge festival and you wind up measuring yourself against people who are streaks ahead of you either in terms of experience or talent or popularity and it is very challenging but also very fun and very good for your work ethic.

It’s really awesome to hear a comedian talk about it like it’s a craft and like, a proper artform and career, rather than just freaking out about their next hour or next spot. Which segues me into the obligatory boring last question: Why should people see you show and what’s it about?

They should see my show because it is really good, comfortably the best I have been since I started and I don’t want that feeling of being at my best to go away ever. The show itself is an hour of absolute nonsense, it is sort of surreal observational stuff, there are some  through lines to keep the nerds engaged but really it is about getting an audience full of people in a room and making sure all of us having an absolutely cracking time.

You can book tickets to Guy Montgomery: Let’s All Get In A Room Together in the NZ International Comedy Festival here.

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