336. Crime Doesn't Pay (The Legend of Zelda: Link's Awakening [DX])
I've mentioned this before, but I started Link's Awakening when I was 4 and somehow missed the hallway going left (ie, to the dungeon-required Roc's Feather) in Tail Cave for 4 years. That meant that (a) I spent an utterly absurd amount of time in the introductory areas and (b) I eventually hit seemingly unremovable barriers in every direction and became convinced I'd have to do something really weird to get through. So I repeatedly smashed all the bushes in the world and bought a bow for 600 rupees. Then the shopkeep replaced it with a shovel for 999 rupees, so I went back to grinding to get that, too. Right before hitting that total, I ran out of bombs (very cheap in LA) and decided to go buy some more. I had a ritual of trying to walk out the door with whatever I was buying, which normally resulted in the shopkeep stopping you and demanding money. This time, I took the long way and waltzed out of the store with free bombs. I went back to the field, gathered up the last few rupees I needed, went back to the shop prepared to (somehow) solve the mysteries with a shovel, and...
...Died horribly when the shopkeep turned out to be Aganhim in disguise. Now-five-year-old me was traumatized, and to make matters worse, I'd saved between stealing the bombs and reaching 999 rupees. No shovel for me.
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On a side note, there's a neat homage to this in Twilight Princess. You can take potions from the bird without paying, resulting in him chasing after you and doing a bit of damage. Alternatively, you can underpay (even just 1 rupee) and he'll just call you a cheapskate.