(Haven't read Red's article yet)
I've been here 14 years which is less than a lot of people, and cracking was well established then. I remember cracking an Amiga game straight off audio data cassette which had an encrypting loader. The mysterious depths of XOR I believe

. Anyway, that must be somewhere between 20 and 25 years ago, and there was plenty of cracked 'warez' around at that time. There were cracking groups before that, communicating by FidoNet and sharing data via direct modem dial-up ftp sites. The internet was in it's infancy and not something the majority of people had acess to unless you were in USA universities. Discussion was by Usenet news groups, distributed via Fidonet.
Of more interest and concern is when did cracking start dying|?
Git (old)