Bingo without the exciting social scene.
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Saying "cruiser" after B11 doesn't make it any more exciting.
All the fun of sitting around pulling random numbers out of your ass, and nothing else. Battleship is a cunning self-referential test of intelligence: If someone thinks it's involved in Battleship, they don't have any. This is a game of relentless random repetition. Even when you score a direct hit, your next four moves are iterating around that spot to find the target. Then you continue in the line those points define until the task is completed. That is exactly the sort of soul-killing algorithm we built computers to do for us.
"I AM PROGRAMMED NOT TO DETECT BOREDOM."
Then Hasbro ruined those computers by building Electronic Battleship. It's another intelligence test. Even regular Battleship was a waste of money, as the game can be played with pen and paper, and now you can give a corporation between $10 and $80 for it. Subtract that cost from 100 and you have your IQ. Paper's advantages are that it's faster, you can't lose pieces, it doesn't make constant goddamn noise, and you don't feel obligated to play it again after you discover how soul-crushingly boring it is.
What You Should Play Instead: Ricochet Robots
Ricochet Robots is a game where numbers don't mock the entirety of human progress. This is a real mental battle, cunningly turning "counting" into a breakneck race of demented machines ramming full speed into solid walls and each other.
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It's another excellent introductory game. The person asking "What?" at the start will be screaming "SEVEN!" with all the intensity and joy of a winning lotto number later that same game. It takes about two minutes to learn, but you'll actually feel your brain upgrading as it forces numbers through faster than ever before.
Risk is worse for family game night than incest. It simulates all the boredom and relentless repetition of trench warfare, but at least people really dying on the Eastern Front wished they were home with their beloved family. You are home, and now you hate the bastards.
"IF YOU KEEP LETTING HER TAKE AUSTRALIA, I WILL FEED YOU BOTH TO DINGOES!"
The worst part of Risk is victory by excruciation. A well-designed game has tactics and skill building to a climax, a thrilling race to victory, and when someone has clearly won, it's because the game is over. In Risk, someone can win hours before it ends, and they will not let you just admit it and leave. They spent hours carefully planning this victory, and by God you are going to sit there and patiently lose for just as many hours so that they can enjoy it properly. They've turned having fun into a zero-sum game.
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"MY JOY IS POWERED BY YOUR MISERY!"
This is the same psychopath who can be in control of two-thirds of the entire world and still whinge about how unfair it is that people are ganging up on them. The one who insists that there are more tactics than "Take Australia and try not to succumb to dice-rolling repetitive strain injury."
What You Should Play Instead: Settlers of Catan
Settlers of Catan is the binary test for "Have you actually played board games, or just terrible family ones?"
Settlers of Catan is the shining diamond to Risk's filthy smog of coal. It has the same ideas of territory control, building resources, and cursing the newly invented and extremely obscene gods you've incarnated specifically to build hells for your fellow players and the number seven like an evil Sesame Street. Except every move matters, it's fun, and it's possible to finish a game inside a day. You even learn the same important life lessons, like how, when it comes down to it, your own mother will destroy you for one chunk of stone.
The big bad, the final boss, the scabbed-over subconscious memory that motivates thousands of bored people to keep changing the channel in silence rather than risk opening the dusty Pandora's Box of family grief perched on top of the cupboard.
"Now with extra bullshit!"
The closest thing Monopoly has to actual gameplay is arguing over which piece you get to be. A fact Parker Brothers admitted by asking the Internet to do exactly that for a new piece, then printing a hundred thousand cat pieces before waiting for the answer, because obviously.
"No, Internet, you totally surprised us with that one."
It's the Constructicon of all terrible games, combining every terrible flaw into one unstoppable monster. You can buy a thousand pointlessly different boards to give them extra money for no reason -- it's entirely based on luck, layered on top of a single broken tactic with a tendency toward the orange properties, and it's the Romans vs. Jesus of victory by excruciation.
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YOU'RE NOT ALLOWED TO QUIT, YOU STILL HAVE ONE MORTGAGED BROWN AND TWO DOLLARS I WANT!
The whole point of the game is proving that capitalism is utterly broken and unfair, and people still play it to get their go at winning. Parents would be better off buying their kids a rack and a My Little Inquisition scalpel set. There's the same aspect of taking turns to torture each other, and at least that way the kids learn about anatomy.
And since we got these new pieces, no one wants to use the car anymore.
What You Should Play Instead: Power Grid
Power Grid is everything Monopoly should have been. You're genuinely aiming to build a monopoly, earning ever-increasing fountains of money, but you still have to spend every cent to stay ahead of the competition.
It's a masterpiece of interlocking game systems. You balance expanding networks, resource levels, and nuclear auctions in a game that upgrades your brain like ENIAC: forcing yourself to run calculations faster than ever before, designed specifically to target cities and destroy your enemies. You can genuinely pull off financial intimidation to win by screwing your enemy out of their last lump of coal.
The game perfectly cascades to a finish, early tactical choices and carefully husbanded resources progressing to mid-range border combat, climaxing with games of Brewster's Millions chicken as players throw fistfuls of cash at each other to claim the last few points. And just when you think it couldn't get any cooler, you learn that the original German name is Funkenschlag.
Who we're assuming is a board-game playing German pop-punk singer.
The Internet connects everyone with all kinds of interests. Getting together to roll cubes is one of the least weird and most fun of those activities, even when it isn't slang. We've got TableTop, the nerdebrity Web series all about board games, and a horde of iPad and smartphone app versions of board games, which kick the shit out of chronocidal iteration bullshit like Angry Birds. So grab your inelastic gravity chaos-to-integer reduction engines, and play.
These control more fantasy worlds than magic rings and Joss Whedon combined.
For more reasons why classic games suck, check out 5 Classic Board Games With Disturbing Origin Stories and Why the Board Game Guess Who Is Getting More Racist.