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To my very limited knowledge, the most difficult software to crack was Steinberg Cubase. Such a PITA the hackers decided not to do it ever again. They quoted a ridiculously large figure for the amount code devoted to detect cracking (~30%), and having a significant impact on performance.

I had links about about bypassing anti-debugging techniques, I'll see if I can get my hands on them again.

Cubase was, by far, the hardest program to find a crack for. I remember a buddy of mine hooked me up with a cracked version that actually worked, but then I reinstalled and lost the files. Never found it again and stopped using Cubase. A year later I just purchased Ableton Live. I know so many people that use Live now because Cubase was too difficult to crack.

The current version of Live on the Macintosh itself took quite some time to crack.

Those guys at Ableton are serious business.

It's at http://www.blackhat.com/presentations/bh-europe-06/bh-eu-06-...

Ok, but not exactly the type of standalone software we are speaking upon, yes? edit: as an aside, adobe's subscription based model could be seen as a way to curtail.