The Guild of Dungeoneering has a cheevo for dying in the tutorial fight - which is actually *really *hard to do because both the player and the monster’s card decks are already set and heavily favour the player ; while the monster only has one “do damage” card IIRC. It’s not quite “break the game”, but I still had fun puzzling it out. It’s a reverse challenge, really - “try to be foolish beyond our foolproof design” kinda thing.
Oh, and in the same vein, I really like that* Pathfinder:Kingmaker* has achievements, not for actually “breaking the game” (in the sense of abusing glitches or hexediting saves or whatnot) but for min/maxing one’s character above and beyond. I haven’t gotten it yet, but I’m currently chasing an achievement for breaking 1.000 damage with a single Monk punch.
I think I’ve mathed out a combination of feats and gear that will allow it (on a crit), but… more testing required 
My favorite is from Fable 3. Marry 6 people and kill 2 after being king. The achievement is called Henry VIII.
Is shooting Shooty McShootface in the face in Borderlands 2 an achievement or just the greatest mission in video game history?
Something I thought while watching a bit of an LP that dollar to donuts is going to be “it was all just a dream” in 10 minutes or so : I think something fun could be done if there was a way for devs/Steam to actually take away achievements earned. I could see two interesting/amusing things that could be done to fuck with the player :
- the rather common tutorial/prologue where the player has every power unlocked and maxed out, is having fun being invisible and smashing tanks with his fists (hi Prototype 2) and you’re racking all kinds of super hard cheevos that would be mechanically hard to set up but the enemies just line up perfectly - I’m talking stuff like “three headshots with the same bullet” à la Deadpool movie, that kind of thing… then you lose them in the invariable depowering sequence/flashback. And have the re-earn “honestly”
- more fun and thought provoking : conditional cheevos, to tie in with the in-game morality system. For example you could get a “living saint” cheevo for being a very good boy, but after earning it you’d lose it the first time you do something bad and can’t get it again. Or maybe something less carictatural but along those lines - give the player himself a meta stake in their character, that kind of thing. Achievements that not only need to be earned, but maintained.
(well, what do you know, 13 minutes, asylum akshully)
Balance, it sounds like you’d make a good beta tester. Beta testing isn’t just about a group of people playing the game; it’s about people trying to figure out all of the edge cases that could cause bugs, so they can be found and fixed before people stumble across them accidentally.
As for dying in a safe zone, I don’t remember all of the details, but Torchlight 2 has an exploitable bug that’s triggered by dying in town. Ordinarily it’s impossible, but there’s a joke item that you get as a quest reward that’s a cursed potion of healing, which does some ludicrous amount of damage to you over time instead of healing you.
Oh, that’s another good category of achievements: Games will sometimes include some sort of super-lethal trap option as a joke, but sometimes it’s possible (with extreme effort) to survive it anyways. But the only one I can think of off the top of my head is one from a (tabletop) D&D adventure: There’s an underground river that a character can fall into, which makes you save every 10’ or something or take bludgeoning damage, and the river doesn’t empty out for five miles, and some guy over on GiantITP figured out how to make a 4th-level character (the intended level for the adventure) who can survive it.
Burlew should figure a way to include that trick into an OOTS strip.
I’m a software engineer and have done plenty of testing professionally. My ability to break software–whether to wreck it or to make it do useful things it wasn’t designed to do–borders on legendary. I consider it a point of pride that I made a game dev call me a bastard (or at least me-too someone who did) on the game’s official forums. 
On the positive side, I generally submit very good bug reports. I like to include clear steps-to-reproduce and sometimes the module (or even line number) where the bug is hiding, if I have access to the source.
Achievement unlocked: Taught grandmother how to suck eggs.
In Civ 6 it’s actually Leonardo, Michelangelo, and Donatello - Raphael isn’t in the game.
“That’s just wrong.” Killing a certain number of jawas with your party jawa with you.
Aww I love Blizz. 
From Crusader Kings II:
Bön Appétit! Eat a character of the Bön religion