I may or may not have done some cracking since the early 90s.
Back then three things were true for me to start that hobby:

1. Had a computer and lots of free time.
2. Had 0 money but friends that would lend me a game for a week or two.
3. Had access to burnable media.

This was mostly me trying to keep playing games after giving the disk (or disks) back.
However, once I might have cracked GTA (the original), the rush of finally understanding how a debugger worked and figuring it out, made actually playing less apealing than the whole figuring it out.

It made me rent games then just try figuring out how to crack them, but that was financially killing me as again I had nothing to begin with and I was now at minus some.

Granted that none of the early protections were anything similar to Denuvo.
In most cases, it was just a case of blocking a cd check here and there. Some had hilarious protections where the game would screw the player if detected: RA2 would be probably the most famous I remember. Often than not it made me paranoid if I had triped a trap and the game was being unfair or bugged.

Somehow I kept going until I shifted towards the Hackintosh scene.

Then when the first humble bundle appeared and people pirated it, it disgusted me to no avail and finally left this part of my life.