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Never broken a controller, I'm usually quite restrained, but I did snap my NFS Prostreet CD in two ouf of sheer disgust of how bad the game was.

I've found myself going for digital copies these days, I blame myself for being too lazy to visit a proper brick and mortar store to pick up a physical copy.

My uncle let me borrow his Sega Megadrive (Genesis for you Americans) and a few cartridges, including the original Sonic game.

I've gotta say Bioshock.
Inversely I'd say Deadly Skies 3, aka Air Force Delta Strike.

It's gotta be ones of the Ace Combat games, can't for the life of me decide which one though.

Pretty sure mine was the original Gran Turismo. Had some great times with that.