What was it like to win Who Wants To Be A Millionaire back in 2001?

Anyone alive and sentient in 2001 probably remembers the heated fervor that surrounded Who Wants To Be A Millionaire? The U.S. adaptation of the British game show that birthed “Is that your final answer?” premiered as a two-week special event in 1999, but didn’t actually produce a millionaire until November of that year. (That’s when winner John Carpenter became a national sensation for using his “Phone A Friend” on the final question to call his dad and tell him he was about to win.)

As the show rolled on, though, producers sought ways to make it more exciting, ultimately landing on a progressive jackpot for a winner. For each episode where no millionaire was crowned, $10,000 would be added to the pot, making audiences wonder when someone would strike it rich.

As it turned out, the answer was April 9 and 10, 2001, when environmental engineer and Michigander Kevin Olmstead ran the board, ultimately earning $2,180,000 and nabbing the record for the most money won on a game show ever. That record has since fallen in the era of multi-week Jeopardy! runs and that show’s Greatest Of All Time tournament, but in 1999, Olmstead’s achievement was monumental.

But what did it feel like for Olmstead, and how did he prep for his rec0rd-setting run? The A.V. Club tracked him down to find out.

The A.V. Club: Let’s start at the obvious place: How did you get on Who Wants To Be A Millionaire?

Kevin Olmstead: At that time, the networks let anyone who wanted to call in try out to be a contestant. They were not doing any auditions to speak of, which was good for geeks who wanted to pick up the phone.

AVC: Why did you want to be on Millionaire? Other than the million dollars, of course.

KO: The money.

I did [the dial-in entrance contests] regularly and even set it up so that I could do it when I was at my office. Because of the way they did it, the questions were similar to the fastest finger questions, so the garbled speaker that was doing the calls would say, “Arrange these words to form the title of a book,” and you’d use the keypad, so it would be like, “Two: Of. Three: Grapes,” and so on. So then you just go “one, three, four, whatever,” and if you did that right three times, you’d get the chance to be randomly drawn to be in a playoff.

If you were drawn into the playoffs and got five questions right in that manner, then hang by a phone because they’re going to call you. So I went through that process, and I think I made it to three playoffs.

On one of those playoffs, I was using a phone at home where it would save up the numbers and say, “Oh, you look like you’re dialing numbers for… let me put that together for you.” That phone is now gone. I remember the question on that one was going be tricky, too, because the question was like “put the people who were in Charlie’s Angels on TV and in the movie in order by age.”

The option that finally took was where I went into a conference room at the office and had a piece of paper where I could write down what is it that they’re looking for and what the order is that I were going, like if they were going biggest to smallest, shortest to tallest, whatever. I sketched it out and then would go ahead and do it. And that’s when it finally took.

So I picked whatever episode to be on, and I was in the circle. At that time, for the competition, anyone who got to New York, their trip was being picked up by the network. That was essentially their prize for getting through all of the above, a three-day trip to New York and being put up in the Empire Hotel, which is right at the Lincoln Center.

So anyway, we go to New York and I’ve taken my mother. We’re told to go up and check that our clothes are right for television because they want to make sure that they don’t have any labels or that sort of thing. It turned out that she had a perfectly nice little jacket with her, but they said it was too loud or something, but I got approved for my shirts.

AVC: It’s cute that you brought your mom.

KO: They put her in a companion chair, and had an assistant producer sitting next to her. So I found out all of this stuff later because they were being shuffled around and talked to while the contestants are off elsewhere.

So you get to the stage, and you sit down in the circle, and then they bring in the contestants that they walk out with or just walked out onto the stage with and play continues [from the previous episode]. We were coming down to the wire at this time, and if the time ran out, then we’re done.

In my case, there was a gal who was struggling with a question on spider anatomy. That question was essentially where on the spider’s body the web material forms, which, in correct terms, it’s in the abdomen, because spiders only have a head and a cephalothorax. So anyway, she’s answering that and the question is phrased really oddly, but when she missed it, I whispered to the guy [next to me], “We’re going to have a chance!”

They had time for one last fastest finger question, which I got, yay, and that got me to the hot seat. Two questions in, hurrah. Then I was set to tape the following episode. They were doing, some days, two episodes a day because they were running and running to stay in the same place.

AVC: I’m surprised they weren’t doing more, frankly, knowing what other game shows do.

KO: Yeah. Normally, your half-hour episodes, you get you do five of those in a day. That’s what they’ve been doing with Jeopardy.

The problem with Millionaire is that you also have the logistics of getting 10 people in. Because ABC has flown them in and put them up at the hotel, that, I suppose, is handy for them because they can put them on a shuttle bus and therefore are able to keep track of everybody.

So anyway. We’re in the break between episodes, wow, and they say “You can eat if you want to,” and I said, “I don’t think so.” I changed my shirt, which was a good thing. Then they checked my mic sound, and I just tried to calm down.

One of the lifelines was Phone-A-Friend, so I had a friend set up in a room so that they knew who to call. So that was one of the callable numbers. That’s what happened with all the Phone-A-Friend, is that they were preset numbers that could be called by depending on whose name you gave.

[Regis Philbin and I then] entered into the studio or maybe made a couple of attempts entering into the studio, and then Regis just started going. I started going with the question directions and we keep going and going.

There was one question [”Who settled and became the first governor of the Utah territory?”] where I went to the audience because I wasn’t sure of where, in the history of the Mormon faith, does Joseph Smith fall versus Brigham Young? The answer was that Brigham Young is the one who made it all the way to Utah. Joseph Smith kicked the bucket in Illinois.

AVC: It was always a question of how much you could trust the audience.

KO: That was the only one where I trusted the audience, and a friend later observed that possibly most of the audience had never heard of Joseph Smith.

The best way to handle that is to keep quiet, keep calm, and say nothing to the audience. You don’t want to gab around and have the audience hear, “Oh, it might be Joseph Smith, but I don’t remember.” You don’t give the audience any reason to vote for a wrong thing.

I had to use the 50/50 because, even though I’m an environmental engineer, I am not a tree hugger. The question was “Which of the following trees is not considered a conifer?” and I somehow had the phrase “cedar cone” sticking out in my head, so I went with Beech, which… Beechnut is a kind of gum.

For the Frank Sinatra question, which is that Quincy Jones worked with Frank [“In the 1950s and 1960s, Quincy Jones directed orchestras for which of these crooners?”], I somehow got that out of my mind, being a Frank Sinatra fan. I remember looking at album covers for Frank and I got somehow the Quincy Jones name into my mind. In retrospect, considering the other answers, the other three answers weren’t cool enough to do things with Quincy Jones.

So at that point, we’ve made it through and I had the $125,000 level in the bag. Then I did some phoning a friend. The friend that I phoned was, at the time, an archivist at Carleton University in Minnesota. He is a coach of quiz bowl there, and he has a list of books and authors, so that’s why we were done in 15 seconds. It would have been done faster but I forgot what I read.

The question was [“What writer collaborated with photographer Walker Evans on the 1941 book Let Us Praise Now Famous Men?”], and so I said, “Here’s the question,” he said “James Agee,” and I said, “Okay, cool.” Afterwards I picked up a copy of the book so I could say that I had it. It’s a sociological tract about tenement farmers in Alabama with accompanying photos by… I forget the guy’s name.

So with that, I have two questions to go. And then we move on to the next question, which is about the Earth’s geography. [”The Earth’s circumference at the equator is how many miles?”] That’s a quick question…

When the final question [”Who is credited with inventing the first mass-produced helicopter?”] showed up, I knew it immediately. And Mom, sitting next to the associate producer, whispered to him, “He’s going to know this.”

So, anyway, everything goes crazy. I was trying to do a dramatic pause. It looks like I’m hyperventilating. That was not the intent. And then what was going through my mind as as I hopped out of the hot seat was walking on a Plexiglas floor that now had confetti on it.

AVC: How well do you remember all of it? It’s been a long time.

KO: 20 years, I know! I have a fan boy in Australia who keeps watching his recording of my episode every year on his birthday, which, okay, fine. The final question is at least available widely on YouTube.

KO: The show’s name is Who Wants To Be A Millionaire?, but you won substantially more than that. How did the actual total factor into your nervousness?

KO: Well, the way I was playing, had I now known the final question, I would have been willing to walk away. They apparently had had a lot of people walking away, and so that’s why [Millionaire creators] Michael [Whitehill] and David [Briggs] thought that kicking up the money amount would sweeten the deal for people to take a shot. But for me, the answer is no.

AVC: People want any money versus no money.

KO: Essentially, that was the problem with Super Millionaire because Super Millionaire said, “Okay, we’re going to take the top prize amount to ten million dollars.” If someone has managed by dint of some work to get to the question at the $5 million dollar level, they have five million dollars in their hands. And so the show says, “Now we’re going to ask you this question and if you get it right, you get $10 million, and if you get it wrong, you’re going to fall back on” whatever the consolation prize was. Who’s going to take that?

I mean, you could see in the normal gameplay that people would throw all their lifelines and get to $64,000 grand. Then they’d take a look at the $125,000 question and say, “That’s all folks.”

AVC: If this isn’t too personal, how did the money pay out? Was it over the course of the past 20 years?

KO: Well, now it comes out annuitized, which is the over the year thing. Essentially, the annuities are the way that lotteries say, “We’re giving away a hundred million dollars!,” when they should be saying “We’re giving away a hundred million dollars over 30 years.” Really, taking it as an annuity is better if you have the chance, so then you spread the money out.

So that’s now what they do. I’m not sure if anyone who won the million ever had the annuity option. In my case, that check that was handed to me on Live With Regis And Kelly, that was the real check, with the routing number, the whole works.

Before I left the green room, I sent the ABC publicity guy who was with me out to the car to get my bag, in which I had the banking information that I was going to put the money into with a new account number. And I endorsed [the check] “for deposit only” to set account before I left.

AVC: I’ve read some articles about about you and I’ve read that you bought a van, but did you get anything else? What did you do for you?

KO: I bought a condo and then didn’t really have enough income to keep it up. I bought a van, but that’s pretty much gone.

But what I do now is that I’m an engineer, and I’m here in northeast Ohio with my husband—that’s the other thing. The post-show publicity blitz was interesting. I might be out to dinner somewhere and might see an older couple, and it’s like the lady of the couple is going, “Ask him! Ask him!”

AVC: I mean, you were fairly famous at the time. You had won quite a lot of money. In fact, you won the most money on a game show at that time. What did that feel like?

KO: I was the record holder on a U.S. game show until Ken [Jennings] passed me and, you know what? If anyone is going to pass you, that’s a pretty good one.

Essentially, I’m just one member of the club of people who were high money earners on game shows. Because I know a lot of people in the quiz community, it became for a while, “How much money has been won by people who have been in my living room?” I knew a couple of people who had been on Millionaire before, so that was an interesting criteria, because if you’re in a tournament with some of these people…

There’s an organization abbreviated TCONA, which is Trivia Championships Of North America and a lot of people in that room are people like Ken. Brad [Rutter], Mr. [James] Holzhauer, all these people who are into trivia games are in that bunch and when these people get together, it’s an interesting experience.

AVC: Looking back on the experience, how would you sum it up?

KO: I was very lucky because things fell just right to get me to New York. Things fell just right in the stack of questions coming out.