My worst one was when I first played Dark Souls (I had no idea it was supposed to be a super hard game) and I kept dying for HOURS in the same area. I kept getting more and more frustrated because I had to travel all the way back to where I fought the boss I was stuck at and then I just got rekt by a basic skeleton soldier and -blam!-ing smashed my controller into the ground and broke it. I NEVER raged in games until then and ever since then I've been so prone to raging. Dark souls broke me...
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This, I think I broke a controller playing that for the first time.