This was a thing until well into the 2000s. VHS stayed around for a long time. We only got our first DVD player in 2003 (it was dirt-cheap - a tiny silver thing the size of a PSOne that cost maybe €35, a small fraction of the price we paid for our VCR in the '90s) and you could still get many of the latest movies on VHS at that point, both legally and illegally. There were regional differences though. From what I’ve heard, my country of Germany held onto this medium for longer than others.

Most piracy (in my experience at least) involved recording TV broadcasts and then duplicating it for friends and family or duplicating content that was otherwise available within your circle. Some people recorded DVDs onto VHS (there were even devices that had both disc and tape drive that did this very conveniently), but this wasn’t that common.

Slightly off-topic, but I had a neighbor who was very proud of being able to circumvent the copy protection and compress movies on DVD to fit onto a single CD (which would still play on a DVD player) at an acceptable level of quality that was somewhere between VHS and DVD (but closer to the latter with the right codec settings). I taught myself how to do this later on as well, although only in order to share movies and shows with others, since I quickly preferred having media on hard drives and USB drives instead of juggling discs around. My personal go-to method was to rent DVDs from the local library for free and then create backups of those I wanted to enjoy more than once. I did the same with PC games and software from that place…

I experimented with this as well, but since I was keeping full copies of the discs on my hard drives anyway, it was unnecessary in my case. I still have most of these disc images; now on my NAS.

I think the first time I tried N64 emulation must have been in late 2002. There were indeed still games released for this system at the time, although not many. Tony Hawk’s Pro Skater 3 (ported to the console in 2002) was one of the last big games for it. Fun fact: The PC version at lowest settings looks almost identical to the N64 port.

Early N64 emulation was spotty, but the fact that it worked at all absolutely blew my mind, especially since I was just in the process of switching from N64 to PC as my main gaming platform. Super Mario 64 was one of the first titles to be properly playable with next to no issues, but outside of that game, it was a bit of a gamble and remained so for years. Performance could vary wildly, glitches were very common (some titles remained unplayable until surprisingly recently, like the excellent voxel-based Command and Conquer port for the system) and the plugin system proved to be a nightmare, as it fractured development resources.

GameCopyWorld is still around today and still being updated. Looks the same as it did decades ago.

My go-to method was to create a disc image of games from the local library and then use either DaemonTools’ copy protection emulation feature or a crack from that site. They had and still have a really good selection of the latest titles (nothing 18+ though, the equivalent of the American M-rating), although it’s almost entirely console games now due to mandatory online activation with most PC games.

There was also software (probably still is) that records the state of your computer before using a program. Then you’d run the program and it recorded any changes (with filters, of course), which you were able to undo with a simple button press. At the time, it was usually a change to some registry entry. This was another method I used to reset timers and usage limits of software like the one you mentioned. As before, I tracked down registry changes by hand until I discovered a more convenient option. This was necessary, because many programs with usage limits left information behind when uninstalled so that you couldn’t just do what you did.

I could swear I did something like this (although obviously not at a kernel level) decades ago with trial versions of software that would only work for 30 days or similar. At first, I did this by hand for the entire system, but I’m pretty sure I had a program for Windows 9x that could independently set time and day for any given application, without affecting the rest of the system.