5Press Your Luck -- Amount Stolen: $110,237
Michael Larson had a part-time job as an ice cream truck driver, but was cursed to look like a wolf digging its way out of a child molester's corpse. This left him a lot of free time to watch game shows and daydream about free money. He taped them and rewatched them, almost certainly to an orchestra of tiny pleas for help coming from his freezer.
When you sit at home watching TV it's only a matter of time until you hit it big, and that's what happened to Michael. After six months of scrutiny, he noticed a fatal, exploitable weakness in the Press Your Luck scoreboard -- the Holy Grail of creepy shut-in discoveries. He left for Hollywood with the last of his savings and despite looking like an oyster dressed as Santa, they put him on TV.
On Press Your Luck, a box spun randomly around a board and you stopped it with your buzzer to win whatever it landed on. The catch was that contestants could land on a Whammy, which was a cartoon monster that took all your money. Michael discovered that there were two spots on the board that never had a Whammy and the "randomness" was actually the same five sequences over and over. With little trouble, he went apeshit on their cash and prizes. He kept winning and winning until they ran over their broadcast time, and Michael ended the day with $110,237. This was by far the most money ever won on a game show and the biggest victory for questionable ethics since the invention of the penis pump. As he celebrated, karma scratched its head. It didn't really know how to deal with something like Michael, but it knew it had to fuck him.
The producers obviously knew something was strange, but since he wasn't technically cheating, they gave him what he won. In 1984, he had what would be about a quarter million in today's dollars. That's so much more than you need to buy happiness if you're the kind of person content with game show rerun marathons. Michael went a different way with it. He invested all of it into a second get-rich-quick scheme: one dollar bills. This nutbar sat among piles of money and frantically pawed through them with his girlfriend in the hopes of matching the serial numbers read off by a radio game show for a $30,000 jackpot. It was as close to the exact opposite of buying happiness as you can get. Karma shrugged while it watched. "This is really weird," thought the cosmic principle.
Like all ideas stolen from the awful children in Willy Wonka and the Chocolate Factory, his plan ended badly. Michael's girlfriend and he left their cash to go to a Christmas party and came back to find it all missing. A burglar had kicked in their door, and after what had to be a whole lot of staring in disbelief, left with all the actual grocery bags full of cash. Michael immediately accused his girlfriend, so she left him and never came back. And as Mr. Larson was left penniless in a drafty, empty home, karma was just getting there and screaming, "Sorry I'm la-- holy shit. What happened here? I was just going to have him never win the radio contest. This is way, way more than I had in mind."
4Million Dollar Drop -- Amount Stolen: $800,000
Million Dollar Drop was a short-lived game show where couples had $1,000,000 they wagered on trivia knowledge. They placed stacks of bills on trapdoors that of course clanked open when they got a question wrong. It was crushing for people to watch their actual dreams fall away, but the demilich beneath FOX studios demanded a sacrifice of cash tainted with despair.
On the very first episode, Gabe Okoye and Brittany Mayi were asked to wager their million dollars on whether a Walkman or Post-It Notes were sold first. They didn't agree, which was perfect because the show let couples bicker for 60 seconds before the trapdoors ended their relationship. Gabe thought the answer was Post-It Notes because of a ridiculous amount of knowledge he had about the product's origin, uses and manufacturing process. Brittany thought it was the Walkman, just because. It was such a caricature of every argument I've had with a woman that my glands started preparing my body for angry makeup sex. "What's that musky smell?" shouted my neighborhood over the yowling calls of a thousand cats.
Gabe eventually won out and they placed $800,000 on Post-Its. Gabe was wrong. The trapdoor opened and said the only thing trapdoors say: "What you once loved belongs to the darkness now." They went on to lose the rest of their money too. The only thing Brittany won on Million Dollar Drop was with the final line of every argument she and Gabe would have for the rest of their lives.
Through a strange coincidence, the show was aired two weeks after a Financial Times interview with 3M inventors about the molecular structure of adhesives. In it, extremely boring people learned that Post-It Notes were test-marketed in certain cities before the Walkman and that Gabe was right. So obviously, the show was happy to admit its mistakes and send brave excavators in to retrieve the cash, right? Not even close. Look at the show's format. A pile of money sits there until a tragic spectacle rips it away unless they win, where literally nothing happens to it. That kind of idea really only comes out of your brain if you're some kind of monster. And so the first thing the producers did was deny their error through a semantic argument over the word "sold." Losing that, they offered to have Gabe and Brittany back on the program. But they didn't do that either since the show was canceled. $800,000 has never caused so much confusion and sadness since I distributed 200,000 throwing stars to the homeless.
The show's host, Kevin Pollak, argued that Gabe and Brittany shouldn't have gotten another shot at the money since they didn't know the final question and would have lost it all anyway. Great point, robot. Now, imagine you'd just won a fight with your wife and it turns out you were wrong. Spectacularly wrong, on national TV, and it cost the two of you almost a million dollars. No one has a point of reference for how psychologically brutal that would be. That's like your marriage counselor exploding during an argument and spelling out SHE WAS RIGHT THE WHOLE TIME with her remains. They weren't in any kind of state to play goddamn trivia games after that. Take a look at this misery:
The producers only made this show because there was no money in sitting at the foot of hospital beds and watching terminal patients die.