In its near three-decade history on air, Who Wants To Be A Millionaire has seen big winners – and an unlucky few who lost out life-changing sums of cash.
Only seven contestants have thus far won the ITV show’s jackpot, but plenty more found themselves tripped up on difficult questions.
In Sunday’s episode, Jen Essery Lillikakis took to the hot seat hoping to win big to pay for an exotic honeymoon with her newlywed husband Kyri, who was seated in the audience.
She tackled the early questions on topics including art, Shakespeare, sportswear brands and cookery with ease, before being left baffled.
Jen’s luck took a big downturn on the £500,000 question, when Jeremy asked her: ‘According to Guinness World Records, which of these has travelled at over 260 miles per hour during a competitive game or match?
‘Tennis ball, ice hockey puck, badminton shuttlecock or table tennis ball?’
She used the sole remaining lifeline, Phone A Friend, to ask her dad Chris, but he didn’t know the answer.
Jeremy issued a stern warning, saying: ‘You are now completely on your own and have no more lifelines. If you get this wrong, if you go for it and get it wrong, you lose £186,000.’
Jeremy also pointed out to Jen that she could choose to not answer the question and walk away with £250,000.
She responded: ‘Would I be more annoyed at giving it a go and getting it wrong… or not giving it a go?’
Jen selected ice hockey puck, only to soon discover the correct answer was badminton shuttlecock.
Reacting to the monumental loss, Jeremy said: ‘Oh my god you have just lost £186,000! It is unbelievable you took a punt on that. You need a bravery award for that.’
Taking it on the chin, Jen said: ‘Well, that’s fine. I have won £64,000’ – due to setting this as her safety net earlier in the game.
Here is a look at some of the other most unfortunate players over the years – as well as the questions that caught them out.
Nicholas Bennett
Nicholas Bennett (pictured) appeared on the programme last year – only to have a heartbreaking end to his game
Episode: May 25, 2025
Amount lost: £375,000
Nicholas, a data analyst from West Hempstead, correctly answered 14 questions before it all went wrong.
On the £1,000,000 question, he was asked: ‘Which of these words, each coined by a famous writer, was derived from the title of a fairy tale about three princes?’
The four options were A) Pandemonium, B) Serendipity, C) Utopia or D) Yahoo.
Nicholas used both the Ask the Host and Phone A Friend lifelines, but neither knew the answer.
He opted to take a risk by choosing D) Yahoo, only to discover the right answer was B) Serendipity.
Duncan Bickley
Helicopter instructor Duncan Bickley faced a question about Amy Johnson’s plane – and ended up with the wrong answer
Episode: October 21, 2000
Amount lost: £218,000
Helicopter instructor Duncan, from Brentwood in Essex, got through 13 questions during his game.
The 14th, which was for £500,000, asked: ‘What was the name of Amy Johnson’s plane in which she flew solo to Australia in 1930?’
The four possible answers were A) Achilles, B) Pegasus, C) Hercules or D) Jason
As Duncan didn’t know for certain, he used his last remaining lifeline: 50/50.
This left Pegasus and Jason – with Duncan believing that as Pegasus was a winged horse, it was the logical answer.
The host at the time, Chris Tarrant, reminded Duncan that not only was £500,000 the most anyone had won (at that point), but £218,000 would be the biggest loss.
Duncan went ahead with the gamble – only to discover the answer was, in fact, Jason after all.
As Duncan didn’t know for certain, he used his last remaining lifeline: 50/50.
This left Pegasus and Jason – with Duncan believing that as Pegasus was a winged horse, it was the logical answer.
The host at the time, Chris Tarrant, reminded Duncan that not only was £500,000 the most anyone had won (at that point), but £218,000 would be the biggest loss.
Duncan went ahead with the gamble – only to discover the answer was, in fact, Jason after all.
Rob Mitchell
Rob Mitchell faced a challenging question about the Oscars trophy – only to end up falling short in the end
Episode: November 1, 2003
Amount lost: £218,000
Rob, a database administrator from Leicestershire, reached the £500,000 question before misfortune struck.
The question asked: ‘How many inches tall is an Oscar statutette?’
The available options were A) Eight and a half, B) Eleven, C) Thirteen and a half and D) Sixteen
As Rob didn’t know the answer, he used Phone A Friend to ask his sister-in-law Moira, who was also in the dark.
He chose to take the risk regardless and went for Eleven – only for the answer to actually be Thirteen and a half.
Eleanor Ayres
Eleanor Aytes faced a question about Norwegian explorer Roald Amundsen only to fall short in the end
Episode: January 1, 2019
Amount lost: £125,000
Eleanor, a proofreader from Cambridge, also came up short on the £500,000 question.
Her conundrum posed: ‘The Norwegian explorer Roald Amundsen reached the South Pole on 14th December of which year?’
She had the options of either A) 1891, B) 1901, C) 1911 or D) 1921
Eleanor used Ask the Audience – and she chose the majority answer, which was 1901 – on 47%.
However, the answer turned out to actually be 1911.
Jim Titmuss
Jim Titmuss was asked about the highwayman Dick Turpin, only he ultimately did not choose the right answer
Episode: April 5, 2000
Amount lost: £93,000
Computer consultant Jim, from Middlesex, reached the £250,000 question before falling short.
His question was: ‘Where was the highwayman Dick Turpin hanged in 1739?’
The four possible answers were A) Glasgow, B) Carlisle, C) Norwich or D) York
Jim used 50/50 leaving only Carlisle and York – only to then incorrectly choose Carlisle as the answer.
John Brandon
John Brandon originally chose not to gamble, but instead opted to play the question and answered incorrectly
Episode: December 23, 2000
Amount lost: £93,000
Railways manager John, from Tunbridge in Kent, also reached the £250,000 question during his stint in the hot seat.
He was asked: ‘Which of these sports has an even number of players in a standard team?’
The four possible answers were A) Baseball, B) Rugby league, C) Netball and D) Volleyball
John at first decided not to gamble and just take the £125,000 – however, he reasoned that Baseball has 10 players, Rugby league has 13, Netball has 7, and Volleyball has 7.
He changed his mind and selected baseball – only for the correct answer to actually be volleyball.
Sheila McHale
Sheila, an IT consultant from Weston-super-mare, reached the £250,000 question during her stint
Episode: February 8, 2001
Amount lost: £93,000
Sheila, an IT consultant from Weston-super-mare, reached the £250,000 question during her stint.
She was asked: ‘Which is the most abundant metal in the Earth’s crust?’
The possible answers were: A) Silicon, B) Iron, C) Aluminum and D) Potassium.
As she was unsure, Sheila used her 50/50 lifeline to leave only Iron and Aluminium.
She chose Iron, but was incorrect, therefore losing £93,000.
Robert Brydges and Judith Chalmers
Past jackpot winner Robert Brydges teamed up with former travel presenter Judith Chalmers in a special episode
Episode: September 9, 2003
Amount lost: £93,000
A special episode saw past jackpot winner Robert Brydges team up with former travel presenter Judith Chalmers.
Together, they managed to reach the £250,000 question before being knocked out of the game.
Their question was: ‘Which of the Great Lakes of North America has the smallest surface area?’
Meanwhile, the four possible answers were A) Ontario, B) Superior, C) Michigan and D) Erie.
They incorrectly chose Erie, with the actual answer being Ontario.
Ken Owen
Promotional products manager Ken, from Kent, reached the £250,000 question before being eliminated
Episode: February 26, 2005
Amount lost: £93,000
Promotional products manager Ken, from Kent, reached the £250,000 question during his game.
This was: ‘Kermit was one of the middle names of which First Lady of America?’
And he had these options to choose from: A) Mamie Eisenhower, B) Edith Roosevelt, C) Patricia Nixon or D) Nancy Reagan.
Ken answered Nancy Reagan, but the right answer was actually Edith Roosevelt.
Jerry Walder
Patent agent Jerry, who was living in Suffolk, went out on a question about which actor was knighted in 1953
Episode: March 4, 2006
Amount lost: £93,000
Patent agent Jerry, who was living in Suffolk, got tripped up on the £250,000 question.
He was asked: ‘Which of these actors was knighted in 1953?’
The four possible answers were: A) Laurence Olivier, B) Charlie Chaplin, C) John Mills and D) John Gielgud.
Jerry used 50/50, leaving only Mills and Gielgud – only to incorrectly take a punt at the former.
Who Wants To Be A Millionaire airs on ITV1 and ITVX.
