I won't say "greatest" moment, but my most memorable one was when I came back from the 1996 Microfest (remember this?) with my dad. Normally knowing my dad, if I can ask even for a box of floppies, it would have been enough to keep me happy. Up until that point I was still using an AMD 386-SX/33 with 4MB RAM. No CDROM drive, no sound card. We came back from that Microfest with those 2 things. And also a pair of 39W speakers. Oh man, the ear to ear grin I had at that time.

For those who remember, most PC games from the 80s and early 90s used to have support for PC Speaker. Not actual speakers mind you, but the tinny 1-bit speaker inside your PC. Sometime in the mid 90s, a lot of games removed PC Speaker support, instead requiring a dedicated sound card to work at all. Games like X-Wing were one of the first to require a sound card. I spent the whole night just playing games, listening to all my games in 16-bit sound! The CDROM drive turned out to be crap (local brand, don't ask), but the sound card I remember as my most memorable gaming moment. It was "just" an ESS 16-bit card. Hardware come and go, but that card was the single most enjoyable time of my gaming life. I'm too macho to tell my dad how much I love him, but yeah, I loved him sooooo much for that. Fighting back tears right now just remembering that moment. Sniff! Thanks dad!