‘The worst thing that’s ever happened to me’: Inside Taskmaster’s best moments

Going into his fourth season of Taskmaster Australia, Tom Cashman is accustomed to our nation’s finest comedians calling him names. In fact, he kind of likes it.

“Some of the contestants I’m friends with, so it’s quite natural joking around,” he says. “But it is [strange tormenting] people like Julia Morris, Dave Hughes, Wil Anderson and Peter Helliar – the generation above me that I grew up watching … When it’s someone you idolise calling you a piece of shit, it’s like ‘Hey, I’m just glad you know my name!’”

Over the past three seasons, Cashman – who stars as the much-maligned referee-type figure, and is also involved in production – and the rest of the Taskmaster team have made a fine art of light humiliation. The show, based on Alex Horne’s hugely popular UK format that has run for a decade, subjects five comedians to strange tasks designed to provoke chaos, creativity and a fair amount of cringe.

The first episode of the new season included Cashman slyly bamboozling “Australia’s sweetheart” Lisa McCune, and Dave Hughes flopping over in the mud while trying to throw balls in the rain. But the real magic, Cashman says, is in the moments that catch you by surprise. Let’s look back at some of the best.

Danielle Walker’s passwords crisis

This infamous task from season one – which brought Cashman, the stoic straight man, to tears – required contestants to guess 26 passwords. Others soon figured out that each word must start with a different letter of the alphabet; Danielle Walker spent more than one-and-a-half hours naming every random word that came into her mind.

“This is someone truly going through a crisis,” Cashman says. The task took so long, he says, production had to pay the entire crew overtime.

“It was the last task we filmed on a Friday and I swear they structure the order of the tasks to mess with you psychologically,” Walker says. “My brain felt like it was melting.” When she watched the footage for the first time, she went even further: “That was the worst thing that’s ever happened to me in my whole life.”

Concetta Caristo and the mystery scales

“When you’re coming up with the tasks, you have a vague idea of what might happen,” Cashman says. The passwords one, for example, was designed for the turmoil Walker experienced. This task ... not so much. “Not in a million years would anyone have ever predicted that someone would think what Concetta thought.”

When asked to record the largest weight on a set of scales on a wall, an increasingly frustrated Caristo spent the whole time driving a truck onto an irrelevant mat on the floor thinking there was some kind of Bluetooth weighing machine underneath.

“It’s the hardest I’ve ever tried not to laugh [at] in my life,” Cashman says. He stayed stone-faced about it for months so it wouldn’t be spoiled for her before the studio reveal.

“Watching this back, I can’t believe it never occurred to me to take the scales off the wall,” Caristo says. “I didn’t win Taskmaster, but I did make Tom cry, which is way better.”

Peter Helliar laughing for nine minutes straight

It is exactly what it sounds like. Although, a little meaner. Peter Helliar was the only contestant given this task: to continuously laugh as long as possible.

“I had a headache for an hour after filming this,” Helliar says. “It was a rollercoaster because I would swing back and forth between fake laughing to real laughing. When I saw Tom Cashman crying and laughing that certainly helped.”

Cashman adds: “I reckon Peter Helliar was actually a bit annoyed. He had a sore neck for a few days afterwards. He mentioned it a few times. And then he found out he was the only one to do it … I do feel a bit bad. But the funny overwhelms the badness. He’s such a lovely and positive person. It’s funny to pervert that.”

Josh Thomas’ sock hunt

Clocking the longest time on this list, Josh Thomas spent one hour and 43 minutes hunting for a toy minivan in a red sock (it’s more entertaining than it sounds).

Others noticed fairly quickly that Cashman was wearing said item. But Thomas instead retrieved and inspected dozens of socks hanging from the exterior of the Taskmaster house. “Towards the end I was deliberately making quite clear puns about feet,” Cashman says. “I reckon I made 20 different allusions to the fact that [the toy] was in my shoe.”

When Thomas eventually realised what was going on, he immediately left the task. “He gets cranky when he’s tired so he was legitimately mad at me after that,” Cashman says.

Thomas was the only comedian unavailable to provide comment for this story. But let’s give him the benefit of the doubt that he’s not still mad about it.

Unholy Fists of the Very Aggrieved Scout

This season two task had contestants collaborate on a short film, each in isolation. Lloyd Langford wrote the script, a kung fu revenge story about a scout avenging the death of a brother. Jenny Tian and Wil Anderson acted. Josh Thomas contributed sound effects. Anne Edmonds did the soundtrack.

“Practically, it was one of the most ambitious tasks we’ve done,” Cashman says. “I’m proud of it! And very impressed at how creative people were. Anne Edmonds is so talented at music. It made me a bit emotional!”

Getting a first-hand glimpse at the creative process of these top-rate comedians is always a joy for Cashman. “If they’ve got 40 minutes to think about a sketch, the first 10 is always them being like “F---! What the f---. I’ve got no ideas … It’s nice to know everyone goes through the same thing.”

Taskmaster Australia airs on Thursdays at 8.30pm on 10 and 10Play. You can watch past seasons on 10Play.

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