We had a tandy with some weird manilla folder-based GUI for a short time, then an acer for an even shorter time, and in that same year, we got a Packard Bell Legend 386SX with 4 megs of ram, 104 megs of HDD, and a 16-mhz CPU.
That system survived floods, beer, me and my younger siblings, storms that took out TVs and stereos, and my early screwdriver-wielding days, and I used it until half way through high school. I loved that thing! I wish my dad didn't throw it out when I had it in storage. That think was built like a tank! 🙁
As for how I came to mac, I remember loving the macs we had in school (except for the G3 scary, fall-and-crush-your-kid machines. I hated those!). I loved the Performas and iMacs. Even as far back as grade school, I loved learning about how and why they worked the way they did. I remember the school's admin gave me his username and password to access everything in the district! I have no idea why he trusted a little kid with that, but I never abused that. Those login credentials carried me until high school!
After some really bad family issues, I had to live with my grandmother for a while. She was terrified of computers, and dad kept trying to get her different machines. The final straw was windows 95. That made her swear off of computers.
When I moved in, I had so many old machines I basically turned the basement into a lab, with parts everywhere, and enough machines to heat my room while I learned on them. I was tinkering with linux, SCO, and BeOS at the time. Grandma became interested again and asked me what I thought she could handle. An iMac G4 was ordered, and she took to it immediately! I remember Dad mocking us for getting a mac, then he watched it boot to X for the first time, with the animated setup guide (10.1.5) and he was dumbstruck.
Grandma now rocks an iPad and I kept and rebuilt the G4 for nostalgia.
EDIT: Renzatek, the gameboy pic made me smile. My kid brother went through several when we were growing up, but by the time pokemon came out, he and I were playing together, I was still rocking my big old classic gameboy. Last I checked, it still worked too!