NEED TO KNOW

• Who Wants to Be a Millionaire aired from 1999 to 2019

• The game show crowned 11 winners during its original run

• Many of the winners kept their day jobs and have since retired

Winning the million-dollar prize on Who Wants to Be a Millionaire was a ticket to instant fame during its primetime run in the early 2000s.

The series originally aired from 1999 to 2002 and had a syndicated run from 2002 to 2019. To win, each contestant had to correctly answer 15 trivia questions. Each question was worth a specific amount of money, and at the start of each round, contestants had the option to either submit their answer or walk away with the money they had won up to that point.

As the show’s primetime era host, Regis Philbin became famous for catchphrases like “Is that your final answer?” Later on, Meredith Vieira hosted the syndicated version from 2002 to 2013, after which celebrities like Cedric the Entertainer, Terry Crews and Chris Harrison took on the role.

Most recently, a celebrity edition of the show premiered in 2020 with Jimmy Kimmel as host. The reboot features celebrities who compete for the chance to send $1 million to the charity of their choice.

Here’s a look at where the winners of Who Wants to Be a Millionaire are now and how they spent their prize money.

John Carpenter (November 19, 1999)

In November 1999, John Carpenter made history when he became the first million-dollar winner of Who Wants to Be a Millionaire. Carpenter reached the final question without using any of his lifelines and famously used his phone-a-friend to call his dad and tell him that he was about to win.

“I didn’t want to seem overly cocky,” Carpenter told PEOPLE in 1999. “From the first show, I knew just about all the answers. I sort of expected to win the million dollars.”

Carpenter was a frugal spender and continued working for the IRS after winning the grand prize. He appeared on SNL the day after his big win and spent his money making charitable donations and purchasing a BMW and a home for his family. In July 2024, he paid a visit to Kimmel’s version of Who Wants to Be a Millionaire to celebrate the 25th anniversary of the game show.

Final Question: Which of these U.S. Presidents appeared on the television series “Laugh-In”?

Daniel Blonsky (January 18, 2000)

Florida-based attorney Daniel Blonsky was the second winner of the million-dollar prize. Blonsky invested most of the money, but in 2025 he admitted to making one “splurge.”

“Emeril Lagasse made us dinner. The dinner, ET paid for part of it, but it was like 15 of us or whatever, and I paid for the overage,” Blonsky told The U.S. Sunin July 2025.“That was my big splurge is I paid for Emeril’s dinner. But for the most part, it didn’t really change what I was doing.”

Today, Blonsky is married with two kids and is the chair of his law firm’s Employment Litigation Practice Group, according to the outlet.

Final Question: The Earth is approximately how many miles away from the Sun?

Joe Trela (March 23, 2000)

On March 23, 2000, 25-year-old Joe Trela’s life changed forever when he became the third million-dollar prize winner of Who Wants to Be a Millionaire. Trela, who was a customer service representative for a computer company at the time, ended up giving much of the money to his family.

“It seemed the natural way to do it. A big house is too much to clean and I can only drive one car at a time,” Trela told The Gilroy Dispatchof his decision in 2006.

In 2017, Trela told Waterbreak that he does freelance voiceovers, attends comic cons and spends time with his wife.

Final Question: Which insect shorted out an early supercomputer and inspired the term “computer bug”?

Bob House (June 13, 2000)

Bob House is another winner of Who Wants to Be a Millionaire who was conservative with his prize money. The then-36-year-old went back to his job as a high school history teacher after his big win in 2000 and helped make his wife and their two kids’ lives easier.

“It never even crossed my mind to quit,” House told Education World at the time. “Teaching is the best job in the world. It’s different every day. It’s great to be with the kids. They keep me young.”

In a 2000 story for PEOPLE, House said he and his wife paid off their student loans with the money, replaced her car and went to see a Broadway show. He also spent a portion of his money on a small airplane after earning his pilot’s license in high school, according to ABC 20/20.

Final Question: Which of the following men does not have a chemical element named for him?

Kim Hunt (July 6, 2000)

The fifth million-dollar winner was high school math teacher Kim Hunt, who used his prize money to transform his life. After winning, he quit his job and started a photography business.

“If not for that experience, I would never have met my wife; I would never have learned to speak Romanian. I would never have had my business,” Hunt told the Jackson Free Pressin August 2013. “I wouldn’t be doing what I am doing now.“

While Hunt told PEOPLE, “I don’t spend much more money than I did before,” he did buy a laptop, a used car and financed a trip to Europe with his winnings.

Final Question: Which of the following landlocked countries is entirely contained within another country?

David Goodman (July 11, 2000)

At 24 years old, environmental consultant David Goodman became the sixth and youngest winner of Who Wants to Be a Millionaire. Goodman spoke with the New York Postabout his plans that summer, however he has stayed out of the public eye since then.

“I need to get a car by the end of the year and I’m probably going to buy a place to live,” he said at the time. Goodman told PEOPLE he did end up buying that car and he also purchased a computer for his younger sister. The rest of the money, he said, went to investing in retirement.

Final Question: In the children’s book series, where is Paddington Bear originally from?

Kevin Olmstead (April 10, 2001)

Kevin Olmstead wasn’t just the seventh million-dollar winner; he also became the winner of the largest cash prize in game show history at the time. The show increased the jackpot by $10,000 for every episode that didn’t crown a winner, so that by the time Olmstead won, he took home a grand total of $2,180,000. Olmstead had also already been a contestant on Jeopardy!.

According to The Ann Arbor Observer, Olmstead continued working as an environmental engineer after he won and purchased a minivan and a luxury condo. He also gave money to his family members and to three universities.

In 2008, Olmstead’s investments dipped when the financial crisis hit. “It’s down to a couple hundred thousand, [but] it was never enough to retire on,” he told the outlet.

Final Question: Who is credited with inventing the first mass-produced helicopter?

Bernie Cullen (April 15, 2001)

Within a week of Olmstead’s win, Chicago-based graduate student Bernie Cullen sped through his questions to become the eighth winner of Who Wants to Be a Millionaire.

“I told [then-host Philbin] that I’m gonna buy a couch, I’m gonna get massages every week — I got my first one [Thursday] — and I’m gonna send my laundry out instead of doing it myself,” Cullen joked one day after his win, per the New York Post.

Like Olmstead, Cullen is also a former Jeopardy! contestant. He has largely avoided the spotlight since his million-dollar win.

Final Question: What letter must appear at the beginning of the registration number of all non-military aircraft in the U.S.?

Final Answer: N

09 of 11

Ed Toutant (September 7, 2001)

Another former Jeopardy! contestant, Ed Toutant won Who Wants to Be a Millionaire on Sept. 7, 2001, at which point the jackpot had increased to $1,860,000.

Toutant was the last winner of the original prime-time Millionaire era hosted by Philbin. He worked as an engineer at IBM until his retirement in 2003.

After his death in 2018 from brain cancer, a graduate fellowship endowment was created in his honor at the University of Louisville’s engineering school, per the school’s website.

The memorial shared, “he ran with the bulls in Pamplona, was a skydiver, traveled extensively and was an avid promoter of the arts community in Austin.”

Final Question: During WWII, U.S. soldiers used the first commercial aerosol cans to hold what?

Kevin Smith (February 18, 2003)

Kevin Smith became the first contestant to win the million dollars on the series’s syndicated version, which Vieira hosted from 2002 to 2013. The retired truck driver had devoted his time to studying for the game show before making his debut in 2003.

“I just reevaluated my life and decided I needed to do what I really wanted,” Smith told the Los Angeles Times in 2003 of his decision to pursue his love of trivia full-time.

Smith also told the outlet that he planned on giving his winnings to his mother and one of his sisters and would not be going on a spending spree.

Final Question: The U.S. icon “Uncle Sam” was based on Samuel Wilson, who worked during the War of 1812 as a what?

Nancy Christy (May 8, 2003)

In 2003, Nancy Christy made Who Wants to Be a Millionaire history by becoming the first woman to ever win the grand prize. Before going on the show, she was a middle school English teacher in Tulsa, Okla., according to News on 6.

“I saw the question come up, and without even the answers, the choices, I just thought to myself, ‘I’ve won a million dollars,’ because I knew the answer cold,” Christy later recalled in a 2024 interview with the show.

Final Question: Who did artist Grant Wood use as the model for the farmer in his classic painting “American Gothic”?

The pressure was on for the 31-day Jeopardy! champion Jamie Ding as he competed on Who Wants to Be a Millionaire? with Ben Affleck. When the pair got to the $250,000 question, Ding, a bureaucrat, was stuck. Did Affleck help him out of a bind?

The Season 5 premiere began with Larry David and his daughter, Cazzie. They lost on the $64,000 question and took home $32,000 for their charity.

Then, it was time for Ding and Affleck. Their pairing brought ack memories of  last season when Jeopardy! host Ken Jennings teamed up with Affleck’s friend and host Jimmy Kimmel‘s “enemy,” Matt Damon. They went on to win $1 million.

“I’m literally here riding this guy’s coattails,” Affleck said. “I’m lucky to be here.”

Ding wore a black suit with his signature orange tie. During his Jeopardy! run, he shared that orange was his favorite color and that he wore it on every episode to bring him luck.

The team played for Eastern Congo Initiative. They flew through the first five questions, easily winning $1,000.

On the sixth question, Affleck believed he knew it, but turned to Ding to make sure he was right. When Ding said he was, he locked in the answer, and they continued their streak. Affleck shared that he was “betting” on Ding during the next question.

The men were on a roll with the questions, but decided to use their Audience Life-line during the $32,000 question. “Unless you specifically ask for more, which McDonald’s sandwich is served with a half slice of cheese?” the question read.

The options were McRib, Filet-O-Fish, McCripsy, and Big Mac. With 50 percent, the audience chose Filet-O-Fish. Ding and Affleck both agreed with that option, chose it, and won the $32,000.

The team deliberated on the $125,000 question, guessed, and got it right. Their episode ended on the $250,000 question. The question was “During the annual Spanish festival El Colacho, men dressed in devil costumes run and jump over what?”

The choices were hot coals, stacks of money, babies, and hats. Ding was shocked at the option of babies and made a surprised face. “When Matt was on this show, I was sitting there like ‘I can answer that, no problem,” Affleck said. “He had this  New Year’s Eve question, which what do you eat? Grapes, was the answer.”

“I didn’t know that. I Google ‘Spain’ and their customs because I said I speak a bit of Spanish and know a bit about the Spanish-speaking world. I Googled the customs and stuff that happen, and this was one of them,” he said.

When Kimmel asked Ding if he knew it, he said he had a guess. “Colacho looks kind of like coals, so that would be mine, but it’s just a guess,” he said.

‘Who Wants to Be A Millionaire?’ Fans Beg Show to Make This Change

“It’s actually the one you were shocked by. It’s babies,” Affleck said.

“Whoa!” Ding replied.

“It’s the devil jumping over babies and relieving it of Original Sin and all that,” the actor said.

“I trust you, Ben,” Ding replied.

“Jamie, how does it feel to be riding Ben’s coattails now?” Kimmel asked.

“It feels good. It’s a team effort,” Ding said. They locked in babies and were right, winning $250,000.

On Jeopardy!, Ding won a total of $885,605, including the second-place prize for his 32nd game. Find out if they win the $1 million for their charity next Wednesday.

Who Wants to Be a Millionaire?, Wednesdays, 8/7c, ABC, stream next day on Hulu

Read the latest entertainment news on TV Insider.

Every day, TVLine’s What to Watch column spotlights new and returning English-language shows (and select movies) premiering or airing fresh episodes across broadcast, cable and streaming — organized below by release time and alphabetically within each slot.

On TV this Wednesday: Larry and Cazzie David compete on “Who Wants to Be a Millionaire,” “The Ultimatum” wraps Season 4, and “Christmas at Sea” heads back to port.

July 22, 2026

Enjoyed this article? Sign up to TVLine’s free newsletter, and follow us on Google or add us as a preferred search source for the latest in TV, streaming and movie news.

Read the original article on TVLine.