Schadenfreude (or: Games that are most fun when things go horribly wrong).
Tim
United States San Antonio Texas
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Schadenfreude. The pleasure derived from the misfortunes of others (and in this case, yourself too). The topic says it all.
This list is dedicated to the games that get better when things go horribly, abysmally, fantastically wrong -- even when they happen to you.
Games where things get better when you can say, "Check this out. It's going to be epic." and mean it.
Here are a few of my favorites, please add your own:
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Judy Krauss
United States Pittsburgh Pennsylvania
but I'm not the only one
My hands are small, I know, but they're not yours, they are my own
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When most of the board is radioactive...and the missiles just keep getting taller.
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Judy Krauss
United States Pittsburgh Pennsylvania
but I'm not the only one
My hands are small, I know, but they're not yours, they are my own
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This one is no fun unless everything starts going wrong. Although a solitaire game, it is best when played in a group (with the person across the table from you rolling your enemy attack dice and vice versa) so everyone can join in on the "Oh, no, were all going to die" fun.
Seriously, limping across Europe with most of your plane falling apart and enemies attacking from all sides, while you wonder if you will run out of ammo and/or crash because because your landing gear is stuck and both your pilot and co-pilot are out-of-the-action makes this game good fun.
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53.
Board Game: Steam
[Average Rating:7.88 Overall Rank:22]

Randall Bart
United States Granada Hills California
Red October
Earth is one of my favorite planets
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The death auction. It's an auction where two players have planned on getting a particular action, and whoever doesn't get it will lose horribly. Since the loser loses, he pushes his bid as high as he can, so the winner of the auction is also badly hurt. It's a lot of fun to watch.
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Tobi R.
Germany Cologne
My GeekBadge is still empty...
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The auction variation:
Nothing better than passing that dreaded wooden egg to a player with no beans left and watch her struggle to include it into her feeble tower!
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Does an excellent job of taking the player through the life cycle of a typical combat mission, starting from the enthusiasm and confidence associated with initial mission planning, the edginess and tension as units cross the line of departure and the frustration and despair when things start to go wrong.
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Scott Smith
United States Duncan South Carolina
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All engines pumped and zero power... Six or seven missiles bearing down on the ship... Cannon stuck in blast mode... Three quarters of the modules used/damaged/slagged... Ship careening across the map at maximum Out-Of-Control level and all the conscious crew are plastered against the bulkheads trying to crawl to the other side of the ship... And it's only Phase 2...
Seen it happen more than a few times...
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RJD
United States Quad-Cities Illinois
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In Crimson Skies - the original beauty from FASA, not the one using clix dials from Wizkids - all players' pre-planned movement for a turn are revealed simultaneously after being plotted in secret with the "Maneuver Template". It shows what moves are possible for your fighter, and requires a little mental gymnastics on your part to determine how it'll all translate to the actual map. Plot poorly and you'll either find your tail being blown off by your enemies while your own guns are pointed at nothing or, worse, you'll crash into a canyon wall.
I was teaching this to some friends on Friday, and one just could NOT get the hang of things. He'd asked to play the biggest, slowest, most heavily armed and armored flying tank I had available, not that it mattered. His flying fortress of a fighter would rumble onto the scene and then turn straight into a cliff face or a lonely building in the middle of nowhere. Even after we let him reboot several times, he still never managed to line up a shot on another plane but instead gave several frightening flybys at the Empire State Building, more a danger to himself than our fighters ever were.
It's difficult to show sympathy when you can't stop giggling. 
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James Sitz
United States
Illinois
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I once ran Sally into a swarm of Zombies to save the team, bearing a chain saw. I rolled all 1's on my dice, rerolled some, and still rolled poorly. She died immediately.
When really unexpected stuff happens, it lends itself well to a more colorful story.
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Elwyn Darden
United States Richmond Virginia
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There is no experience in gaming quite like the moment when, in desperation, you are forced to try an area weapon on a room filled with monsters, and you find out that it causes them to fragment. (Think: Sorcerer's Apprentice from Fantasia)
My record is a room with 23 fragments.
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Elwyn Darden
United States Richmond Virginia
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A great favorite with my group and one I have never won but always enjoyed.
My first game I had a great team of horses with the best possible endurance... and I had my whip stolen from me by another player.
There was the time I was beaten out of third place (that fourth place has been my best showing ever in 8 car competetion) by a charioteer who had fallen from his car, gotten tangled in the reins, and was dragged to death ahead of me.
Another outstanding moment was in a game where an opponent went into a curve just a bit too fast, ever so slightly, so that he only had to worry about flipping his chariot if he rolled an 18 on three dice. The odds are 215-to-1 that you will be able to guess what happened next.
Or how about those times that someone flips over in front of you and forces you to changes lanes, or even stop entirely.
Just when I think I have seen all the ways possible to lose a game, someone suggests we play Circus Maximus again and I realize my education is not complete
"There are more things in heaven and earth, Horatio, Than are dreamt of in your philosophy."
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Elwyn Darden
United States Richmond Virginia
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Nothing like having your canoes trampled by Hippos.
I had a friend once who decided that being captured by hostile tribes was not all that bad compared with going back to England and raising a new expedition. So when he finally escaped his captors he headed East not West and sought to make the first trip across the continent. He would find village after village, tribe after tribe, and would approach everyone in "an open and friendly manner". He would inevitably be captured by some, languish a while in their village, and make his escape and continue East.
Once you are reduced to a single man, with a ration or two, and no gifts, you pretty much suffered all you can.
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Elwyn Darden
United States Richmond Virginia
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When things go wrong.
The game begins with the players managing a ramshackle network of ill-fitted rail lines in the Old South. The Union Army keeps taking critical junctions, "liberating" your best paying customers, cutting your lines, destroying your engines and rolling stock, and, just when you think you might complete the best run you have had all year, your own War Department orders you to drop your current cargo and deliver tents to the troops in some distant sector.
You can sense a bit of Scarlett O'Hara in the game, and that is appropriate for the theme.
I know of no other game on the American Civil War that so successfully creates such a pall of doom. You can really feel the Anaconda.
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Elwyn Darden
United States Richmond Virginia
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The game uses a "luckless" combat resolution that is based on each player giving orders to each unit, using inverted counters indicating what each unit is supposed to do in the "Combat Movement" Phase. If any unit cannot complete its planned movement, any unit that was supposed to enter its hex is now jammed. This can create a situation where one section of your line is thoroughly jumbled. Since combat values are related to facing, your disoriented line is either ineffective or highly vulnerable.
Guessing your opponent's intentions and devising a sudden thrust or shift that will best discombobulate him is the heart of the game.
You can really have an impenetrable line fall apart is one turn, which is pretty much what happened in real life.
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64.
Board Game: Dune
[Average Rating:7.63 Overall Rank:91]

Christian Link
United States Basalt Colorado
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"It looks like CHOAM Charity for you."
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Siegfried Steurer
Austria
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Cant believe this wasnt posted already. Nuff said.
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Shane Beck
Australia Not Applicable
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You rolled a 6? Off to Chinatown for you. Let's see if you visit the brothel, fan tan gambling, opium den or the tongs. Getting out of Shanghai ahead of the communists? Let's see if you dodge the assassins first....
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david landes
United States oak hill Virginia
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Wait, I can't feed my monsters and their leaving?.. no, now I'm more evil.. OMG and here comes the Paladin.
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Jeff Q
United States Odenton Maryland
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It wouldn't be a game at all if things did not go horribly wrong!
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Jeff Q
United States Odenton Maryland
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It's much more fun when someone pushes just ONE step too far, and dies.
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Jeff Q
United States Odenton Maryland
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I have heard (though I do not own the game) that it is very possible to have an entertaining sequence of cascading consequences.
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Jeff Q
United States Odenton Maryland
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It's a very boring game if things go according to the novice nun's plans.
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Phil Campbell
United Kingdom Ilkeston Derbyshire
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If it ain't going horribly wrong (for everyone else) then you're doing it wrong!
There's nothing better than taking out someone else's block with a well placed thermo-bomb, cutting off their power supply leaving their blockers limping around their block like a one-legged man with a ball and chain or taking out their water tank and playing Mr Pyro with some fire-bombs! 
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Neil Christiansen
United States Mount Pleasant Michigan
OOK! OOK! OOK!
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"Armut!"
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Nate Lawrence
United States Bristow Virginia
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"Lalala, I'm only one tile away from walking out of here with 50,000G!"
*falls into catacombs*
*spends 6 turns lost but gets more gold on the way*
*finally gets a catacomb exit, also one tile away from dungeon exit*
*draws a bottomless pit card*
"NOOOOOOOOOOOO"
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Bret Clifton
United States Spokane Valley Washington
"You can buy anything in this world with money"--Lucifer
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The game only ends when someone has no more points.
I have 23 cubes worth of wood and a 6 cube 1 level truck...great
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