“I just want to say that I really was trying” – Ray O’Leary talks Taskmaster

Season four of Taskmaster NZ is about to hit screens, featuring a fresh cast of foolhardy contestants including Ray O’Leary, who joins Steve Newall for a chat about the unique experience of being on the sometimes torturous show.

One of TV’s great formats is back on screen next week, with the return of Aotearoa’s Taskmaster Jeremy Wells and his doting sidekick Paul Williams. This season they’ll be putting another well-assembled quintet through the wringer—as described by TVNZ: Actor and comedian Sieni Leo’o Olo aka Bubbah, comedy veteran Dai Henwood, the hilarious accidental actor Karen O’Leary, all-round funnywoman Melanie Bracewell and the second O’Leary vying for the coveted golden bonce, comedian and writer Ray O’Leary.

Since 2015, the original UK series—hosted by the acerbic Greg Davies and creator Alex Horne—has built a global following as it subjected various casts of comedians to a particular breed of humiliation: public failure at pointless tasks, sometimes painfully obvious to the audience. It’s not the first place comedians have had the opportunity to embarrass themselves (and it certainly won’t be last), but the show has really nailed its concept, and inspired Taskmaster series in Australia, Belgium, Croatia, Denmark, Finland, Norway, Portugal, Quebec, Sweden, Spain and the US alongside our New Zealand version.


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The three local seasons to date have delivered superbly, and as with the original series, a big part of Taskmaster NZ is spending a whole season getting a (sometimes frightening) better insight into the personalities on screen. That’s all the more true watching them struggle—or occasionally succeed—through ten episodes of lateral thinking challenges and tests of logic, coordination and creativity, all subjected to intense scrutiny and post-analysis by Wells.

While we await seeing Ray O’Leary’s efforts following in the footsteps of fellow local Taskmaster alums including the likes of Angella Dravid, Laura Daniel, Josh Thomson, Kura Forrester and Guy Montgomery (who shared his Taskmaster experiences with us in 2021) we joined him for a chat on the eve of the first eps airing.

Our conversation has been edited for length and clarity.

FLICKS: I imagine Taskmaster has a huge impact on your normal life and routines during filming.

RAY O’LEARY: It was definitely a big weight on my mind. Even just now, I was just setting up a modem before you called me—but even in my head, I was like, “This feels like I’m doing a task, an incredibly boring task, but it feels like I’m doing this task.”

I was fully in it, definitely when the show was filming, and yeah, the night before it was all I could think about. Like, “God, I have to get up tomorrow and do something and I have absolutely no idea what they’re about to ask me to do”. It’s incredibly stressful—but that’s what makes it so exhilarating and fun to do.

The show seems like a real bonding experience for the contestants, not just each season, but collectively over time.

It feels that way. It’s almost embarrassing, I feel, how close all five of us grew together, just over the course of filming the studio segments, which is done in a week. But, you know, you go through the baptism of fire. The five of us—and Paul to an extent—have all just been through this insane experience that nobody else has been through… and we couldn’t talk about it to each other.

And then we get to sit there in front of a live audience and watch our stupidity unfold in front of all of us. And it’s just a baptism of fire that no one else gets to experience, no one else can relate to, no one else can talk to you about apart from those people. We’re all very close now because of it.

Did you take cues from previous contestants, in terms of what – or what not – to do?

Exclusive scoop: Ray O’Leary has no respect for Guy Montgomery. Put that in your article. It’s got nothing to do with the show, but just let everyone know.

Sometimes I would have a task to do and I remember watching Josh Thomson. And it was also easy for him to come to mind because he was directing the days out doing the tasks, so he was always there. But I would remember he had such an incredible ability to build machines and machinery and do things like that. And I always remember thinking, “God I can’t do that”. And so it sort of pushed me to take a more lateral and maybe lazier option… well lazy compared to Josh’s mechanical brilliance.

The other thing about Taskmaster is that when you get that time limit—you know, when you open up the envelope and you see there’s only 15 minutes for you to do something—you don’t have time to be “how can I be more like Laura Daniel, Brynley Stent”, or whoever. It’s like a pure, unfiltered id comes out you know, your true horrifying self. And the first idea you have is basically the first idea you have to do—because you don’t have enough time to sit around and brainstorm and come up with, you know, the best, excellent, funniest idea ever.

You don’t have time to compare yourself to anyone, you’re just being this awful, sincere version of yourself that comes out.

It really does look like a battle between battle against yourself and a battle against panic.

I mean, I would describe every day as a struggle with myself—but, yeah, especially in the show. I don’t know if you pick it up from watching the show, but listening to Paul say, “all the information you need is on the task” is one of the most infuriating things you can hear in your life. But there’s a lot of panic, like every time I stepped into that room, or you know, wherever the envelope was, I always thought “I’m the only person doing this task. This one is going to be a prank on me. There’s some trick, there’s some prank. I don’t know what’s going on”.

It’s a show that encourages paranoia and hysteria. And I think that comes through in some of the creative choices I make.

You think to yourself “I should have done this, I should have done that.” And afterwards, you go “Of course, that was it. I just got it. I’m such an idiot.” And then you get into the studio and you watch and you see someone else did it even better, which I guess is the whole point of getting five different people. You realise, I guess, how insane your idea was. And of course, this was the proper way to do it. And of course, I completely missed it.

Taskmaster was a show that filled me with regret. You know, there was there was never a moment where I came out of a task thinking, “Oh, I nailed that.” Every single time I was like, “Oh, I’ve missed something. There was a trick. What was it? Should I have looked in Paul’s pants?” I just did, you know, so many insane things with you sellotape and wheelchairs and balloons and was never proud.

And then you’ve got Jeremy Wells pointing out exactly how bad things went…

That’s worse—there’s someone whose job it is to judge you and point out how demented you are. The other thing about Taskmaster is that you know something’s either gone really right or really wrong when they play you first or last. That’s a good rule of thumb for the show, I think. I definitely felt like I got played last a lot—and not for a good reason. There was one task I definitely felt like I nailed, but for the most part, I would say every time I realised what tasks they were about to show us, I would say, “oh, no, not this one“.

I would say I spent about 80% of my time in the studio with my head in my hands thinking, “Oh, God. So what have I done, what have I wrought upon these people?” I remember once in the studio, during an ad break, we’d just been talking about everyone else’s attempts. And Jeremy said, “Don’t worry, you haven’t seen Ray yet”.

That definitely felt like the vibe for a lot of it, where sometimes I was impressed with how much I managed to zig where everyone else zagged. There were a few tasks where I felt like I was completely different to everyone else; there were other times where I was just completely in line with what everybody else did.

And then there were a few times where my inability to do the task was just beyond comprehension. I don’t want I can’t spoil it, but one of the producers came into the room after I did a task and said they always think about how the task could go wrong. And they never once expected me to be able to ruin the task in the way that I did. Well, not ruin, but they never expected a grown adult to lack such a basic skill that I lacked that was so central to the task.

But that’s what Taskmaster does, it really shows how your brain works and what abilities you bring to the table. And my table was quite bare.

You know how a really good computer hacker might become a security consultant, does your inability to perform some of these tasks offer any career prospects?

Maybe they could get me back in to do dummy runs of all the tasks to see if we gave someone with absolutely zero skills, zero ability to function in the modern world, could this task still be done? And if the answer is yes, but just, then you know you’re onto a good task.

With one of the tasks, I remember Mel was sitting there looking at me going like, “what are you worried about?” Like, you know, we’ve seen all the different ways it could have possibly gone. What else could have happened? And I was just “Oh, Mel…”. But you think “here’s the right way to do the task”. And you know, there was a clear right way to do the task and sort of a clear wrong way to do the task. And, it turns out, there was an even more wrong, more embarrassing way to do the task—which I unlocked.

It’s truly embarrassing. I can’t believe it’s gonna be on TV. I can’t believe everyone’s going to see that. I think that one… maybe the way Jeremy scores it might cause some outrage. Because I’ve seen so much of the show or clips have popped up on Facebook or whatever, I’d think “Oh, I can’t be as good as this contestant” and it forced me to go in a completely different way that nobody else in the cast decided to explore—and it turns out for good reason.

If Taskmaster is an evil scientific experiment on comedians’ inability to function – and it might be – perhaps there’s a control group of civilians out there doing it too. How do you think everyday people would get on?

I think there’d be just as much floundering, just as much panic. You know, you watch the task and think “Oh, I could build that” or “I’m pretty good at arts and crafts,” and then you’re in the room and you’re painting a sandwich blue, and you’re like, “What am I doing with my life?”

I believe the sandwich is one that doesn’t get seen, but I did paint a sandwich blue, and no one ever has to see the monstrosity that I created. But it is a horrible scientific experiment, and I think everyone would panic. Everyone flounders under those kinds of insane conditions. The other thing I feel like I should note, is that I don’t know if it’s obvious to tell from how the tasks come out—but I just want to say that I really was trying, you know. I was actually putting an effort, and that’s what I hope the audience can at least see. Maybe what I did was dreadful. Maybe what I did was terrible. But, you know, I was trying my hardest.

How some of the tasks turned out suggests there’s only so far that trying can take you, it turns out. But you know, some of the other contestants, what they were able to bring to it floors you and it makes you think “God, how come I can’t do that? How did I not think of it that way?” It’s truly embarrassing, you know,

That’s the main takeaway that I want to give out. I really was trying and maybe the results, maybe what you see on screen doesn’t seem like I was trying, but I really was trying.

Taskmaster NZ starts Monday, 7.30pm on TVNZ 2 and TVNZ+ and continues on Tuesday.