The original Sims was genuinely innovative for its time, and oddly subversive in a Theme Hospital kind of way.
The Sims 2 set the series on its trajectory of offering increasingly anodyne, smoothed-over features and utterly cynical cashgrab DLCs, however it had some of the old charm and is the one I remember the most fondly because I played it to death in my uni days. The best thing about it was that you could manipulate the facial feature sliders to produce some absolute grotesques, then breed them together to create even more disgusting children. Later iterations of course made sure you couldn’t do this, fucking idiots at Maxis who wouldn’t know fun if it bit them on the bum.
Sim City 2000 was one of the first video games I ever seriously played. My dad had it on his laptop and I was constantly badgering him to let me play it. I could never figure out why, after my city got to a population of about 20k it would suddenly start decaying, whole districts going derelict. I tried everything to stop it from happening, different designs and builds etc but nothing worked and I got really frustrated and even distressed about it. Turns out my dad’s laptop couldn’t handle a larger population than that, and that was how the game coped with the load. Note to video game developers: Please don’t design your game to do this.