I was fortunate enough to have a dad in IT with an interest in games, so I remember going pretty sequentially from DOS to Win 3.11, to Win95, Win98 and onwards from the early 90s-to 2000s on the family computer. I made up my own system from hand-me-downs from whatever my dad didn't want when he upgraded bits.
The gaming evolution was much the same. Doom, Duke 3d, Terminal Velocity into Quake, Quake II, Half-Life, Homeworld, Unreal, etc. basically in order. I remember going from a Voodoo 2 to Geforce 3 to run UT2004, and then an ATI Radeon card so I could run CS: Source.
There are times I'd give anything for my old PC back with a partitioned hard drive and dual-boot into either XP sp3 or 98. Better days.