For every good idea, there are a lot more bad ones. We make unfathomable amounts of dumb decisions every day. That’s why narrowing the all-time worst faux pas to a list of 16, as Bracketology has done, is so difficult. Please enjoy, but don’t get any ideas.
SWEET SIXTEEN
1. Invading Russia in Winter vs. 16. Licking a Frozen Flagpole
Invading Russia during the brutal, bitterly cold winter might seem like a much worse idea than touching your tongue to a freezing flagpole. However, in reality, Hitler and Napoleon attacked for the same exact reason as the kid from “A Christmas Story” licked: their pride led them to believe that the cold wouldn’t be a big deal. Even the results were the same: All three got stuck! I guess the stakes were kinda different though.
EDGE: Russian Winter.
8. Introducing a Band to Hard Drugs vs. 9. Introducing a Band Member to an Annoying Girlfriend
If “Behind the Music” has taught me anything, it’s that only two things can break a popular band apart: hard drugs and soft jugs. Yet how do we decide which influence is worse? Simple. Take The Beatles. Drugs only made them better. Yoko ruined everything.
EDGE: Girlfriend.
5. “Sports Illustrated” Cover Jinx vs. 12. Madden Cover Jinx
If you’re a famous athlete and you agree to appear on the cover of “Sports Illustrated,” something bad will happen to you — you’ll invariably lose a big game, pull a hammy, whatever. But if you appear on the cover of the Madden video game franchise, you could, I don’t know, get convicted for dog-fighting. And remember, America hates dog murder even more than human murder.
EDGE: Madden.
4. Prohibition vs. 13. Feeding a Mogwai After Midnight
The only thing stupider than giving Mogwais food after midnight (and thereby turning them into restless, bloodthirsty Gremlins) is denying Americans the right to drink (thereby turning our country’s population into restless, bloodthirsty Gremlins).
EDGE: Prohibition.
3. Going on the Titanic vs. 14. Caulking the Wagon and Floating it (in “Oregon Trail”)
Boarding the Titanic seems idiotic now, but remember that none of the passengers knew about the iceberg, the importance of life boats or Kate Winslet’s selfishness. When you’re crossing a river while playing “Oregon Trail,” though, you’re given a conscious choice: Are you going to take a ferry across? Hire a friendly Native American guide? No. You’re going to caulk the wagon and float it. Dumbass.
EDGE: Caulking.
6. “Not Having Sexual Relations” vs. 11. Having Sex in a Horror Movie
Which is the more harmful instance of hanky-panky: Is it having sex while a killer is on the loose when it is an ironclad horror movie law that “Virgins Live, Sluts Die?” Or were the Executive Office escapades of the Slick Willie even more misguided? The Presidency hasn’t seen such carelessness since...well, I guess it’s seen a lot of carelessness. But still.
EDGE: Sexual Relations.
7. New Coke vs. 10. The Segway
Both of these innovations represented unnecessary and spectacularly unsuccessful “improvements” to things people already liked: regular Coke and walking. But at least Coke was able to cut its losses by reintroducing “Coca-Cola Classic.” The Segway has joined Crocs and the Myspace gang sign as the symbol of lame people everywhere.
EDGE: Segway.
2. Selling Your Soul to Satan vs. 15. Selling Your Soul to Milhouse
In one of my favorite “Simpsons” episodes, Bart makes the ill-fated decision to sell his soul to Milhouse, who promptly resells it for Alf pogs. But at least that’s better than making a Faustian bargain with the devil. Satan is cunning, relentless and a surprisingly good fiddle player. Good luck, mortal.
EDGE: Satan.
ELITE EIGHT
1. Russian Winter vs. 9. Annoying Girlfriend
Girlfriends have ruined some of the best bands ever, but Mother Russia is the trickiest temptress of all.
EDGE: Russia.
12. Madden Cover vs. 4. Prohibition
America doesn’t really mind when bad things happen to football players. Quite frankly, it’s the reason we watch football. But this nation is nothing — nothing — without its sweet, sweet booze.
EDGE: Prohibition.
14. Caulking the Wagon vs. 6. “Sexual Relations”
I mean, it’s not like Bill Clinton thought he would get caught. But when you caulk the wagon, you know you’re basically ordering the deaths of two party members, three oxen, a wheel and an axle. Murderer.
EDGE: Caulking.
10. Segway vs. 2. Selling Soul to Satan
Would you sell your soul to attain your dream? You know what? You just might. But would you ever purchase a Segway? Of course not.
EDGE: Segway.
FINAL FOUR
1. Russian Winter vs. 4. Prohibition
Prohibition has no bearing on our lives now, but the Russian winter is potentially the reason we’re not living under a Nazi regime. That’s a pretty good bad idea.
EDGE: Russian Winter.
14. Caulking the Wagon vs. 10. Segway
Segways have helped disabled people immensely. Caulking the wagon (or, heaven forbid, fording it across the river) only helps the suicidal.
EDGE: Caulking.
CHAMPIONSHIP
1. Invasion in Russian Winter vs. 14. Caulking the Wagon
Yes, invading Russia in winter has caused unbelievable amounts of death and destruction. But at least Napoleon and Hitler came somewhat close to conquering. When you caulk the wagon in Oregon Trail, you’re basically facing certain computer death and you’re saying “whatever.” That’s the epitome of a dumb idea. (And yes, I caulk every time. Who cares if I never make it to Oregon? It’s good to be bad.)
CHAMP: Caulking the Wagon.
MVP: Meager Rations.

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