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Home / Entertainment

Ray O’Leary on comedy, travel and preparing for the Best Christmas Comedy Show

NZ Herald
5 Nov, 2025 04:00 AM4 mins to read

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Ray O'Leary speaks to the Herald about all things comedy. Photo / Supplied

Ray O'Leary speaks to the Herald about all things comedy. Photo / Supplied

Ray O’Leary had New Zealand in stitches in season four of Taskmaster New Zealand, and recently took his unique brand of comedy to the Melbourne Comedy Festival.

Now the Whanganui-raised comedian on the rise is busy preparing for the Best Christmas Comedy Show On Earth.

The 36-year-old took a moment, under a busy highway, to chat to the Herald about all things comedy, personal bests and his recent exotic adventures. Take his answers with, uh, a grain of salt...

Where does this email find you?

Standing under State Highway 1, trying to log into the free wifi at Mt Eden Corrections Facility to answer your questions.

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What’s been going on in your life recently?

I have begun writing next year’s show, and I try to draw from real life. Unfortunately, my life has been very dull, so I’ve begun trying to draw from other people’s conversations I overhear on the bus or the train. Annoyingly, everyone seems to be speaking about the same thing. They’re all saying, “Who is that guy and why is he writing down everything we’re talking about?” How am I supposed to get inspired?

We see you visited Vanuatu recently. Tell us a bit about your trip?

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It’s an excellent place, and I implore everyone to go. There are lots of adventurous things to do, like I went down rapids, jumped off platforms into the clearest water you’ve ever seen, and learnt about their traditional weaving by having a spider put on my face. A highlight was seeing the water music, which the Vanuatu women make by drumming the surface of the water, and seeing anyone within earshot come over and watch cause they could tell they were seeing something special.

I went with a film crew, and the director was insistent on getting shots of me running, which were very difficult to film as I move so quickly it does not show up on camera.

What are your summer plans?

I’ve grown up with a single mum, and most summers she sends me to camp. But last year at camp, I discovered I had an identical twin and we were separated at birth, so over the summer I am going to take his spot at his dad’s place, and he is going to take my spot at my mum’s place, and we are going to try to trick our parents into getting back together. We’re calling it “The Trap For Parents”.

Comedian Ray O'Leary stars in The Best Christmas Comedy Show on Earth. Photo / Supplied
Comedian Ray O'Leary stars in The Best Christmas Comedy Show on Earth. Photo / Supplied

You are part of the Best Christmas Comedy Show on Earth. Tell us a bit about it?

It is the greatest comedy show on the planet, and that is being printed in the newspaper so it must be true and 100% endorsed by the Herald as factual (the Herald also endorses everything else I have ever said). (Ed’s note: This might not be entirely true). It’s a line-up of some of the best comedians you’ve ever seen, and also me. The New Zealand stand-up scene is in a really great place right now, with so many of our artists going on to massive international success, so it’s your chance to see them while their tickets are still affordable.

What should people expect from your set in the show?

After watching the musical artist P!nk perform, I have decided that I will do my entire routine while being flung by ribbons and wires across SkyCity. The show will be run at a loss, and it will be very difficult to hear what I’m saying above the screaming (both mine and the audience).

What’s the best comedy show you’ve ever been to?

The Best Day After New Year’s Day Comedy Show on Earth.

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Favourite comedian or comedic inspiration and why?

Ultimately, all my inspiration is derived from our lord and saviour, the alien ruler Xenu.

What are you most excited about right now?

I recently achieved my personal best at the gym and can now lift 10 cars over my head with one hand.

What’s one thing you want people to know or pay attention to right now?

The book Doing Good Better by William MacAskill. A lot of people complain about the world as it is and this book shows you how you can make a positive difference to the world how to maximise that impact.

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See Ray O’Leary at the Best Christmas Comedy Show On Earth, a fundraiser show for the NZ Comedy Trust, on 28 November at SkyCity Theatre.

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