Who wants to become a millionaire? The biggest losers ever and the questions that hit them: Contestant to miss out on £186,000 after Phone A Friend disaster
In the almost thirty years that Who Wants To Be A Millionaire has been on the air, it has had big winners – and a few unlucky ones who lost life-changing sums of money.
Only seven contestants have hit the ITV show’s jackpot so far, but many more have stumbled over tough questions.
On Sunday’s episode, Jen Essery Lillikakis sat in the hot seat hoping to win big to pay for an exotic honeymoon with her newlywed husband Kyri, who was in the audience.
She easily answered initial questions on topics such as art, Shakespeare, sportswear brands and cooking, before being left stunned.
Jen’s luck suffered a major setback at the £500,000 question, when Jeremy asked her: ‘Which of these, according to Guinness World Records, has traveled at a speed of more than 260 miles per hour in a competitive game or match?
‘Tennis ball, ice hockey puck, badminton shuttle or table tennis ball?’
She used the only remaining lifeline, Phone A Friend, to ask her father Chris, but he didn’t know the answer.
Jeremy warned sternly: ‘You are now completely alone and have no lifelines left. If you do this wrong, if you go for it and do it wrong, you will lose £186,000.”
Jeremy also pointed out to Jen that she could choose not to answer the question and walk away with £250,000.
She replied, “Would I be more annoyed if I tried and got it wrong…or if I didn’t try?”
Jen selected a hockey puck, but quickly discovered that the correct answer was a badminton shuttlecock.
Reacting to the huge loss, Jeremy said: ‘Oh my god, you’ve just lost £186,000! It’s incredible that you made an issue of that. You need a bravery award for that.’
Jen took it on the chin and said, “Well, that’s fine. I won £64,000 because I set this as a safety net earlier in the game.
Here’s a look at some of the other most unlucky players over the years, as well as the questions that stood out to them.
Nicholas Bennett
Nicholas Bennett (pictured) appeared on the program last year but suffered a heartbreaking end to his match
Episode: May 25, 2025
Amount lost: £375,000
Nicholas, a data analyst from West Hempstead, answered fourteen questions correctly before it all went wrong.
When asked for £1,000,000, he was asked: ‘Which of these words, each coined by a famous writer, is 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 decided to take a risk by choosing D) Yahoo, but discovered that the correct answer was B) Serendipity.
Duncan Bickley
Helicopter instructor Duncan Bickley was asked a question about Amy Johnson’s plane, but ended up getting the wrong answer
Episode: October 21, 2000
Amount lost: £218,000
Helicopter instructor Duncan, from Brentwood in Essex, answered 13 questions during his game.
The 14th, which cost £500,000, asked: ‘What was the name of Amy Johnson’s plane on which she flew solo to Australia in 1930?’
The four possible answers were A) Achilles, B) Pegasus, C) Hercules, or D) Jason
Unsure, Duncan used his last remaining lifeline: 50/50.
This left Pegasus and Jason, with Duncan believing that since Pegasus was a winged horse, this was the logical answer.
The then host, Chris Tarrant, reminded Duncan that not only was £500,000 the most anyone had won (at the time), but £218,000 would be the biggest loss.
Duncan took a chance, but discovered that the answer was ultimately Jason.
Unsure, Duncan used his last remaining lifeline: 50/50.
This left Pegasus and Jason, with Duncan believing that since Pegasus was a winged horse, this was the logical answer.
The then host, Chris Tarrant, reminded Duncan that not only was £500,000 the most anyone had won (at the time), but £218,000 would be the biggest loss.
Duncan took a chance, but discovered that the answer was ultimately Jason.
Rob Mitchell
Rob Mitchell was faced with a challenging question about the Oscars trophy, but ultimately came up short
Episode: November 1, 2003
Amount lost: £218,000
Rob, a database administrator from Leicestershire, had reached £500,000 in demand before disaster struck.
The question was asked: ‘How many centimeters long is an Oscar statute?’
The available options were A) Eight and a half, B) Eleven, C) Thirteen and a half and D) Sixteen
Not knowing the answer, Rob used Phone A Friend to ask his sister-in-law Moira, who was also in the dark.
He decided to take the risk anyway and chose Eleven, but the answer was actually Thirteen and a half.
Eleanor Ayres
Eleanor Aytes was asked a question about Norwegian explorer Roald Amundsen, but ultimately came up short
Episode: January 1, 2019
Amount lost: £125,000
Eleanor, a proofreader from Cambridge, also fell short of the £500,000 question.
Her riddle was: ‘Norwegian explorer Roald Amundsen reached the South Pole on December 14 of what year?’
She had the options A) 1891, B) 1901, C) 1911 or D) 1921
Eleanor used Ask the Audience – and she chose the majority answer, which was 1901 – at 47%.
However, the answer actually turned out to be 1911.
Jim Titmuss
Jim Titmuss was asked about the highwayman Dick Turpin, but he ultimately did not choose the correct answer
Episode: April 5, 2000
Amount lost: £93,000
Computer consultant Jim from Middlesex reached the £250,000 ask before falling short.
His question was, “Where was 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, but then incorrectly chose Carlisle as the answer.
John Brandon
John Brandon originally chose not to gamble, but chose to play the question and answered incorrectly
Episode: December 23, 2000
Amount lost: £93,000
Railway manager John, from Tunbridge in Kent, also reached the £250,000 asking mark during his time in the hot seat.
He was asked, “Which of these sports has an even number of players on a standard team?”
The four possible answers were A) Baseball, B) Rugby League, C) Netball and D) Volleyball
John initially decided not to gamble and just take the £125,000, but he reasoned that baseball has 10 players, rugby league 13, netball 7 and volleyball 7.
He changed his mind and chose baseball, only because the correct answer was volleyball.
Sheila McHale
Sheila, an IT consultant from Weston-super-mare, reached £250,000 in demand during her stint
Episode: February 8, 2001
Amount lost: £93,000
Sheila, an IT consultant from Weston-super-mare, reached £250,000 in demand during her stint.
She was asked, “What is the most abundant metal in the Earth’s crust?”
The possible answers were: A) Silicon, B) Iron, C) Aluminum and D) Potassium.
Unsure, Sheila used her 50/50 lifeline to leave only iron and aluminum.
She chose Iron but was wrong and lost £93,000 as a result.
Robert Brydges and Judith Chalmers
Former jackpot winner Robert Brydges teamed up with former travel presenter Judith Chalmers in a special episode
Episode: September 9, 2003
Amount lost: £93,000
In a special episode, former jackpot winner Robert Brydges teamed up with former travel presenter Judith Chalmers.
Together they managed to reach the £250,000 asking before being eliminated from the game.
Their question was, “Which of North America’s Great Lakes has the smallest surface area?”
Meanwhile, the four possible answers were A) Ontario, B) Superior, C) Michigan, and D) Erie.
They incorrectly chose Erie, when the actual answer was Ontario.
Ken Owen
Promotional product manager Ken, from Kent, reached the £250,000 ask before being eliminated
Episode: February 26, 2005
Amount lost: £93,000
Promotional product manager Ken, from Kent, reached the £250,000 ask during his play.
This was: “Kermit was one of the middle names of which First Lady of America?”
And he had the following options to choose from: A) Mamie Eisenhower, B) Edith Roosevelt, C) Patricia Nixon or D) Nancy Reagan.
Ken answered Nancy Reagan, but the correct answer was actually Edith Roosevelt.
Jerry Walder
Patent attorney Jerry, who lived in Suffolk, set out to find out which actor was knighted in 1953
Episode: March 4, 2006
Amount lost: £93,000
Patent attorney Jerry, who lived in Suffolk, stumbled over 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, but he wrongly took a kick to the first.
Who Wants To Be A Millionaire airs on ITV1 and ITVX.