Remember John Carpenter, the First Winner of “Who Wants to Be a Millionaire?” Look Back at His 1999 PEOPLE Interview

The iconic win was 25 years ago!

On the precipice of becoming the first-ever winner of Who Wants to Be a Millionaire? in 1999, John Carpenter knew there was one last thing to do: Call his dad.

In the now-iconic moment, Carpenter, who would become the franchise’s first-ever winner on Nov. 19, 1999, told host Regis Philbin he’d like to use his lifeline to call his parents after being asked to name which U.S. president had been on the television show Laugh-In. When his dad picked up, Carpenter famously said, “I don’t really need your help, I just wanted to let you know that I’m going to win the million dollars.”

“Because the U.S. president [who] appeared on Laugh-In is Richard Nixon. That’s my final answer,” he said.

“I didn’t want to seem overly cocky,” Carpenter, then 31, told PEOPLE of his performance on the show for a December 1999 cover story. “From the first show, I knew just about all the answers. I sort of expected to win the million dollars.”

The history-making win was followed immediately by an appearance on Saturday Night Live alongside musical guest Sting and host Jennifer Aniston.

The appearance came as part of the episode's now-foreshadowing cold open, which saw Darrell Hammond as Donald Trump announcing his run for presidency and Carpenter as his running mate.

“I come from total obscurity," Carpenter said of his time on the show, which included schmoozing with cast members and standing on stage with Aniston as the episode came to a close. "This is not my life. It was surreal. I thought the highlight of my 15 minutes of fame would be an interview with the wacky drive time guys on WPLR in New Haven, Connecticut.”

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His win secured him guest appearances on shows including Good Morning America, Entertainment Tonight, Access Hollywood, Late Night with David Letterman and of course, Live! with Regis & Kathie Lee.

“Tony Bennett stopped by my dressing room and told me Friday night was the best thing he’d ever seen on TV,” Carpenter told PEOPLE at the time of his appearance on Letterman. “I was just floored. What a gentleman.”

His friend and neighbor Melissa Parnoff said there was an “irony” to it all, as “John is so anti-pop culture. I had to drag him kicking and screaming into pop culture, and now he’s a pop-culture icon.”

PEOPLE described Carpenter as “an intense, wiry IRS investigator” who at the time of his win had been married just 15 months to his wife, Debbie, who appeared alongside John on the 1999 PEOPLE cover.

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He “ripped through his 15 questions with cold-blooded cyborg efficiency to win the first million-dollar jackpot on Who Wants to Be a Millionaire,” PEOPLE said of his performance, as he “became the biggest money winner in television history.”

Philbin himself described Carpenter as having “ice water in his veins” and being “a little on the cocky side.”

“And, yes, the network’s a little poorer now, but this could give the show a shot in the arm,” Philbin continued of the moment.

When PEOPLE spoke to the Carpenters following the big win, the two didn’t share any over-the-top plans for the new cash — which at the time PEOPLE explained would net out to $600,000 after $400,000 in taxes. Their wish list included “that J. Crew leather jacket for Christmas,” Debbie explained, as well as a trip to Paris. John joked that he would donate his money “to the Red Sox to help them sign another power pitcher to complement Pedro Martinez.”

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They also discussed pursuing some home improvements and the possibility of expanding their family: “We’ve been talking about a family, having nothing to do with money,” Debbie said. “Of course money makes it easier and moves things along.”

In terms of leaving his job with the IRS following the payout, at the time Carpenter spoke positively of his experience with the government agency, though with the newfound “cushion” said he might spread his wings.

“I’ve had a positive experience with great people,” he said. “But I have thought about expanding myself. Wondering if there’s something new. Now I have a cushion. I could start over fresh. I’m still a young guy.”

Carpenter, who caught up with The Washington Post in 2020, was still working at the IRS nearly 20 years later. 

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