Top 30 Times Contestants Outsmarted the Taskmaster

#30: Tim Key Throws a Teabag“The Poet and the Egg”

Our first entry comes from the very first days of “Taskmaster”, and is potentially the first instance of someone really knowing how to play the game. Actor, writer and poet Tim Key went all in on his task, though it’s hard to say he really found a loophole or just bent the rules. The task of throwing a “teabag into a mug from the furthest distance” immediately inspired Key, who was delivering a laundry list of necessary items, whilst other contestants were still figuring out where the house had the longest room. Through a cobbled together delivery system of plastic sheets and tennis balls, it was a hole in one for Key, who’d go one to become a "Task Consultant" for every series thereafter.

#29: Matthew's Paranoia

"The Clever Side?”

The task "Completely fill the yellow box with sand" had both Jason Mantzoukas and Matthew Baynton realise there was a trick. Of course, why wouldn’t there be; this is “Taskmaster” after all. As the other contestants had to stay holding the box they’d picked up before reading said task, our two actors knew better–albeit for different reasons. Baynton's distinct British attitude of just knowing it'll inevitably go wrong, just about edges out Mantzoukas' Americana-attitude of everything will be alright. The former’s paranoia leads him to notice the red-herring a tad quicker, and gets the best time, with the use of both hands.

#28: Katherine Parkinson's Lying Down Approach

"Dog Meat Trifle"

Scientists suggest that, since time equals space, the fastest way of travelling between two points is by bringing them together. Clearly, actress Katherine Parkinson secretly knew that, as here she was, applying that same logic to… neatly putting clothes on a rail in the fastest time. And she did it, lying down. Literally. Without her feet leaving the safe zone, and playing on the fact she didn’t have to be standing, she rather ingeniously pulled the rail closer and got to work. Shame, despite clearly being a physicist, she didn’t notice the hangers. Admittedly, Parkinson’s time on “Taskmaster” turned out to be a gem that no-one expected, but is now historic.

#27: Rhod Gilbert's Satsuma in a Sock

"The Pendulum Draws the Eye"

By this point, Rhod is a Taskmaster legend, often through insulting Greg Davis, which given that the Taskmaster can, (and did) deduct points, probably wasn’t the wisest idea. What was particularly wise, was how close to the borders of cheating Gilbert could be, without crossing them. It’s on full display here – twice, as he initially tries to bend the rules one way to find the sock with the tangerine-instead-of-pool-ball without feeling, sniffing or punching them… but his luck was in during his quest for scissors. Instead, he finds a satsuma in the kitchen, and simply adds one to a random sock, reasoning that the fruit “didn’t have to be exclusively in there.” He’s not wrong!

#26: Andy Zaltzman's Bad Ass Painting

"I'm a Girl Who Likes a Clean Line."

Sometimes, contestants can outthink the Taskmaster, or find a clever workaround in a very subtle way. Andy Zaltzman, who as well as a comedian, is a professional statistician, clearly drew on the details here. The prize task wasn’t particularly elaborate: Bring the thing most likely to make Greg say: "Oh, Christ, now that is badass!" For Andy, that was simple: take it literally. He painted a donkey, very poorly, or–in other words, a bad ass. Whilst the Task did mandate that those six words had to be stated, there was nothing about adding a seventh tiny one–just one letter, ‘a’. Being detail-oriented served Andy well overall–he won the series.

#25: Robins Puts the Baby in the Corner

"Some Impropriety?"

It’s hard not to believe even “Taskmaster’s” assertion that comedian John Robins might be their greatest contestant. We could’ve focused on how he immediately found the grabber to hook a toy out of the box, or his very clever deduction when tasked to "Create Tension," that it could be physical, not emotional, as implied. However, our favourite, is how he completed the “Jobstacle course.” The baby, (or, jug of water) can't leave the baby carrier... but, Robins – to audience shock, quickly notes that the baby carrier can leave him. Setting it to one side, meant he spilled 0% of the contents during the physical course. All that Robins’ lacked was conviction in himself!

#24: Bonus Jason

"Getaway Sucks"

To put it bluntly, Jason Mantzoukas is “Taskmaster’s” proof that appearances really can be deceptive. He and his fellow series 19 contestants are tasked to simply "place something somewhere surprising," with big bonuses awarded if they provide the most surprising answer to Greg asking "How did that get there?" At first, Mantzoukas appears to have completely failed… What's so special about a banana peel in an under-counter cupboard? But those bonus points flooded in when footage showed Mantzoukas somehow delivering the banana into the hands of his semi-naked self. Did Jason have magic powers or employ video trickery? Nope, just a good old fashioned doppelganger, in Nish Kumar.

#23: Hugh Dennis Brings Alex his Dinner

"No Stars For Naughty Boys"

The task itself is a glorified obstacle course, through which contestants have to bring Alex his dinner… which would be fine, had they not been tricked into standing on one leg and now can only use that one. Whilst the others were hopping mad that they couldn’t adjust their posture for the route, the “Mock the Week” star had a better idea… adjust the route for his new posture. With a handy pair of scissors, he hopped to the line barriers, and cut them down… meaning Alex was well fed with food, and Hugh with points.

#22: Bob Mortimer Unties Himself

"A Wind-dried Puffin"

There is a contingent of people that, rightly believe, that Bob Mortimer is a National Treasure which should be protected at all costs. If you needed any further proof than his irreverent comedy then look at when “Taskmaster” tried to tie him up with rules. The contestants were asked to stand in a noose, and then begin the task. What we often forget is that Bob Mortimer used to be a solicitor… and those skills of dissecting the wording of documents; or lack thereof, came in very handy here. Unfortunately, those documents didn’t include atlases, it seems, since only naming three countries meant he shared first place with Mark Watson–who named half the world.

#21: Rhod Gilbert's Hole-in-One

"Twelve Blush Majesty Two"

Gilbert returns to prove how creative he really is. This is especially true when he–like Bob Mortimer–focused on what wasn’t written into a task; and then went much further with a literal loop-hole. Most would be deterred by the quantum physical dilemma of making something out of nothing – i.e. the void of a golf cup – but not the ADHD-powered Gilbert: It wouldn’t be allowed on the green, but by moving the area around it, the Welshman easily nabbed a hole-in-one.

#20: Paul Sinha’s Easy Finish

“Aquatic Sewing Machine”

Known for being a destructive quiz machine on “The Chase,” Paul “The Sinnerman” Sinha joined the “Taskmaster” crowd for series 8. For the task, “Make this beach ball cross the finishing line,” contestants had to move a beach ball to the finish line the fastest by only using water to touch the object. Rather than haphazardly spray the ball with a hose, Sinha decided to make the task far easier. He took the finish line and brought it closer, only requiring a fraction of the spraying power to finish the task. However, the time Sinha spent rebuilding the finish line caused him to finish with 4 points, as Iain Sterling skipped the course to take top place.

#19: Alice Levine's Big Bubble

“The Bubble Brothers”

Upon hearing the title of the task, “Make the biggest bubble and burst it with your nose,” most folks will picture making an air pocket with washing up liquid. After all, pretty much every participant did. But not radio DJ Levine. Joining the “Taskmaster” cast in series 6, she went about making a massive bubble from a black bin bag, successfully arguing that a bubble is essentially a ball of air with a membrane. With a lot of effort, Levine managed to pop the bag with pins taped to her nose. The presenter’s bubble came to a whopping 50 centimetres, over double the next biggest with Liza Tarbuck’s 20.3-centimetre attempt, earning Levine 5 points.

#18: Rylan Clark's Unique Perspective

“The Fastest Duck”

Sometimes, Greg Davies likes to cause havoc with his judgement. And in this case, we’re siding with him due to the ingenuity involved. In 2021, the first “Taskmaster's New Year Treat” series aired that featured non-comedians battling it out. For the solo episode contest, TV presenter Clark used his noggin in the task, “Get the biggest thing through the doughnut.” With the plastic cow statue that Clark named “Linda” after his mum, he used forced perspective camera trickery to make it look like the hefty item went through the treat. At 800,0000 cubic centimetres, it was the biggest by far, with 9,000 in second place. With the temptation of annoying the internet, Davies let it count and gave Clark 5 points.

#17: Tim Key's Ice Vanishing

“Down an Octave”

Now, while Davies can make stellar decisions…he can also make terrible ones. In the first series, the contestants were given the task, “Make this ice block disappear as fast as possible.” The self-explanatory mission had the majority melt it with hot water and/or smash it to bits. But Key had another idea. Using a wheelbarrow, he took it to the river and lobbed the block in. After 13 minutes and 40 seconds, Alex couldn’t see the ice anymore. So, with the next quickest time coming in at 17 minutes 4 seconds, Key should’ve been held aloft for his inventiveness. Instead, Davies decided it would take the ice an hour to melt and put him in last place, making this the biggest “Taskmaster” scandal ever.

#16: Johnny Vegas Watches Himself

“Hippopotamus”

Alex has perhaps never looked as creepy as he was for this task. In series 10, the contestants had to “Draw the animal that is watching you,” with the caveat that they couldn't leave the room, the animal was wearing a hat, and they had to keep looking at the mirror. With the real animal hidden behind the mirror with a switch that cost them time, Vegas didn’t search for the supposed object as he realised he was both an animal and wearing a hat. So, he did a self-portrait. With impressive artistic skills, considering Vegas had to look in the mirror, he pulled off a pretty good drawing. So much so that he netted 5 points!

#15: Sally Phillips’s Special Delivery

“Their Water's So Delicious”

When a task involved a camera, actor Phillips knocked it out of the park in series 5. After all, her intimate water cooler clip and the birthing of adult Little Alex Horne were iconic. But apparently, coconuts are another forte of hers. As everyone struggled not to touch the ground for “Get this coconut as far from here as possible,” Phillips remained seated and got Alex to send hers to the Prime Minister of Fiji. However, because coconuts are restricted by Fiji, the package stayed at the Post Office. But hope isn't lost! Due to the building being 1.1 miles, or 1770 metres away, Phillips destroyed Bob Mortimer’s second place of 33 metres to get 5 points.

#14: Noel Fielding Gets in the Fruit Bowl

“Hollowing Out a Baguette”

With shows like “The Mighty Boosh” and a long history of surrealist comedy, Fielding in “Taskmaster” was always going to be a spectacle. Appearing in series 4, Fielding’s standout work was for the task “Camouflage yourself.” Contestants had 10 minutes to hide themselves and another 10 to stage the photo. When Fielding’s interior caravan photo was displayed, we were really confused, as nothing looked out of the ordinary. And then, after zooming in on the fruit bowl, we see a little waving Fielding mimicking a banana. Using a green screen and his yellow costume to appear like the fruit, he bamboozled Davies, earning him 5 points.

#13: Sitting Bridget Christie

“The 75th Question”

You have to love literal thinking when it comes to “Taskmaster.” In series 13, the “Record the highest number on this pedometer” task was handed out. Most of the contestants did the obvious, complete some exercise or utilise objects to mimic movement to trick the pedometer for 20 minutes. Chris Ramsey nearly gave himself heatstroke with his attempt! Christie first tried some super weird, unsuccessful movements. But then, she had a lightbulb moment. She sat on the pedometer and then recorded herself on her phone saying the largest number she knew, “11 trillion gazillion.” While the “gazillion” part wasn’t included, since it’s a made-up figure, “11 trillion” was accepted, which destroyed second place at 2,789 steps.

#12: Mel Giedroyc’s Store Success

“Spatchcock It”

It’s always fun watching the contestants read the task multiple times to try and understand it or figure out a loophole. When comedian and presenter Giedroyc did just that, we could practically see the cogs in her noggin turn. In series 4, the contestants were given 10 minutes to “Get this camel through the smallest gap.” The men, for some reason, went with destroying the camel cuddly toy to squeeze it through things. Giedroyc had another idea. She took the teddy to the shop Baby Gap and ran through the building with it clutched in her hands. She made it out with 12 seconds to spare! Because Giedroyc took it through Gap’s smallest brand, technically doing the task, she got 5 points!

#11: Rhod Gilbert Turns the Tables

“I Can Hear it Gooping”

There may not be as chaotic a contestant as the Welshman. If he wasn’t mocking Davies with his childhood or THAT picture of him, he was making Little Alex Horne incredibly uncomfortable. In series 7, we had “Tie yourself up as securely as possible,” with the goal that the slowest time it takes Alex to untie a contestant wins. But, rather than do what's expected, Gilbert tied up Alex and later his own hands. However, an earlier task, “Put on a boiler suit and lie flat on the ground,” came into play. If he hadn't forgotten about the klaxon's meaning, Gilbert might’ve been first in both. Instead, he had to settle for winning the tying and coming second in the boiler suit.

#10: Katherine Parkinson’s Coconut Extraction

“Moments of Silence”

Taskmaster wouldn’t be the show it is without the hilarity of watching celebrities fail miserably at simple tasks. In Series 10, the contestants were presented with various tools to help them extract a tablespoon of water from a coconut as fast as possible, but not before adding one final fruity twist. Some decided to smash it open, believing everyone else would be too concerned with choosing a less obvious method, but this was hardly an original thought. Katherine Parkinson, however, headed to the fridge and conveniently found a carton of coconut water to drink with ease. Her unique interpretation of “extraction” won her “points for style” as well as the top spot in the task despite not being the quickest.

#9: Mawaan Rizwan’s Bin Juice Cocktail

“Hippopotamus”

Also during Series 10, everyone was given the straightforward task of making the prettiest and tastiest cocktail with the coolest name, but they had to achieve all of this without making a noise over 60 decibels - around the same volume as normal conversation. The assortment of glassware, metal utensils and ice proved to be a noisy cocktail in itself, and with every mistake they had to pour their hard work into the bin and shout a phrase. Mawaan Rizwan turned this unfortunate fate to his advantage, though, as his bin filled with more and more ingredients. Mawaan’s bespoke “bin juice” cocktail was born for Alex to enjoy, or at least try to.

#8: The Contestants Hack Charades

“The F.I.P.”

In the finale of the third series, the celebs split into groups to play charades with a few added rules. Wearing foam fingers at all times and with a 500-foot river separating them was more than enough to grind their gears. Dave Gorman decided that acting out his cards would be too much work, instead recruiting adventurer and TV presenter Ben Fogle who just happened to be passing by for a photoshoot. While the rules stated that the contestants may not raise their voices, that didn’t apply for those not involved in the game, meaning Ben could shout every answer across the river, bagging the team an impressive score of 19 out of 20.

#7: Al Murray Takes A Pea On A Journey

“Pea In A Haystack”

The Series 3 contestants were asked to “propel” a pea the furthest distance, to land and remain on a red carpet. While the majority began flinging their pea with no particular technique, Rob Beckett noted that “propel” simply meant to move something with force or drive, and proceeded to stroll around the garden with the pea in a wheelbarrow for 414 metres. However, it was Al Murray who took this ambiguous definition much further, quite literally, as he rolled his pea in the carpet and heaved it into a taxi, travelling up the motorway for nearly 18 miles. The £150 cab journey was a small price to pay for Taskmaster success.

#6: Roisin And Tim Utilize Alex

“The Pie Whisperer”

Show creator Alex Horne oversees all tasks and often calls the shots when it comes to fair play, but being in the vicinity of the contestants can lead to grim circumstances. In Series 1, when Roisin Conaty and Tim Key had to guess the contents of five pies without “breaching” them, they realised that the rules didn’t technically apply to Alex. Roisin ordered Alex to taste the pies and guessed what might be inside based on his reaction. However, she “created her own hurdles” by not looking at him as he ate them. Tim used the superior method of asking him to smash the pies so he could see what was inside, allowing him to win the task comfortably.

#5: Richard Osman’s Grammatical Interpretation

“Fear Of Failure”

As die-hard fans of “Taskmaster” will know, deciphering the exact words of the written instructions is key. The wording of one task in Series 2 caused some controversy. Some enlisted help from the public, while others were more full-on, rolling and kicking the balls up the hill with varying amounts of success. For Richard Osman, reading the instructions a second time revealed an obscure use of grammar, and he resolved that he could collect the mat and take it directly to the exercise balls at the foot of the hill. After a confused call to lexicographer Susie Dent, it was confirmed this was a valid understanding of the instructions, and Richard got to enjoy “Taskmaster” success and a less intense workout.

#4: Joe Lycett’s Zero-Second Victory

“No Stars For Naughty Boys”

Series 4 of Taskmaster brought us both hilarious and impressive moments, and what greater way is there to outsmart the Taskmaster than completing a task before it has even begun? That’s exactly what Joe Lycett did during a tiebreaker task in Episode 7. After entering the lab, he saw a jar of mayonnaise covered in vaseline and predicted exactly what the task would be. He then opened the jar before even reading the instructions. Although guessing the nature of the task was quite straightforward, it was a stroke of genius by Joe to be proactive and complete it before anyone could start a timer. This allowed him to win the task in an unbeatable zero seconds. It doesn’t get much better than that.

#3: Mark Watson Sheds Some Light

“The Leprechaun or the Lesbian”

“Taskmaster'' is extra special when a contestant manages to be clever yet still execute the task terribly. Series 4 contestant Hugh Dennis had many memorable moments, notably his clever solution to drawing someone he couldn’t look at directly by getting a mirror from the house. Mark Watson in the following series, however, swiftly asserted his dominance when tasked with painting a rainbow in a dark room, with only glow-in-the-dark brushes and paint pots. While everybody struggled, Mark did an obvious thing that everyone missed - he turned on the light. Yet, like Hugh, Mark still managed to create questionable art, despite his astuteness. Even so, his lightbulb moment had the other contestants kicking themselves for not being so sharp.

#2: Keep Alex Dry

“Tarpeters”

Tasks requiring effective teamwork often best reveal how well contestants respond under pressure. One team set themselves apart in Series 6 during a mission to keep Alex dry while he sat under a shower that would turn on after two minutes. While the first team haphazardly covered him in bin bags and other items in a mostly failed attempt, the second team calmly considered their options. They eventually disconnected the hose from the shower, establishing a safe distance between Alex and the flowing water. They even had time to make him a dry martini, as well as point hairdryers at him, resulting in an even drier Alex than at the beginning, and leaving the Taskmaster thoroughly impressed!

#1: Hugh Dennis’ Basketball On A Treadmill

“Look At Me”

Taking our top spot is the moment in Series 4 where Hugh Dennis gave it his all to achieve a time score in a task that was completely unsurpassable. In order to keep a basketball on a running treadmill for as long as possible, forbidden to touch both the basketball and the treadmill, Hugh covered the basketball with a large tub for stability as the treadmill began to speed up. This proved to be effective, but he decided he could do one better by asking Alex to bring the extension cable to him so he could pull the plug and cease the entire operation. With his basketball spending an extraordinary 4 months unmoved, he was much deserving of his round of applause!

Have you been keeping up with “Taskmaster” around the world, or are you solely rooted to the UK version? Let us know, in the comments.