Ultima Underworld.
Saved a whole year for that one. Took a whole day to figure out how to configure the EMM386 line that would enable me to have enough memory to run the damn thing (tears of frustration were shed).

Absolutely worth it. Blew my little mind. Never got to finish it though, because of a bug in the quest in the last level T_T

World Grand Prix for the Sega Master System 2.

Technically the second ever game I owned, as the system came bundled with Alex the Kidd in Miracle World.

Was maybe 6? at the time.

One of those handheld football games with little red dots for players.

If you mean console or computer games, asteroids for Atari 2600.

The football game was too hard for a 5 year old.

I still like playing an occasional game of asteroids to this day.

Couldn’t tell you the very first game I bought, but I definitely remember one of the oldest being either Ed Edd n Eddy: The Mis-Ed-Ventures for gamecube or Sonic Unleashed for PS2.

I could at least say with certainty my first Steam game purchase was most likely Portal 2 since I wanted the level creator super bad as an xbox port owner.

I think it was either Soleil or Dune 2 for the Mega Drive/Genesis. I was 10 or 11 at the time.

The first game I ever bought with my own money was Metal Gear Solid 1. And the PS1 to play it on.

Super Mario All Stars bundled with a SNES. I remember going to the supermarket with my grandmother to get it.

Pokemon Blue. I saved up then learned about sales tax at the cashier, so my dad bailed me out with the extra $5

I can’t remember if I ever bought a NES game but I know I bought the SNES with turtles in time with my own allowance money when I was like 8 or 9. First PC games was Theme park and Transport tycoon deluxe bought at the same time.

Crash bandicoot 3.

Considering how uninformed I was back then, it was a hell of a success.

With my own money: Link to the Past. Most definitely.

Illusion of Gaia at an Alco for Christmas. A great SNES game. Graphics have aged very well and gameplay is still solid. It’s an ARPG like Zelda kind of. Lots of puzzles. Swap out your character for other heroes occasionally to tackle different puzzles/dungeons.

I was pretty young, around 11. It was in the clearance bin, like 30 bucks. I was initially kind of disappointed because most of the games there we had or they sucked. But that one stuck out. Was definitely worth it.

A couple Christmas(I was 13) later I got FF7 for PC. I had previously beaten 1 and 3(6). FF6 was great. I’d play that game start to finish in about 8 hrs. Which really isn’t that bad for 100% run.

Then I got really into StarCraft (bnet) UMS games. Cat v mouse varieties were especially fun.

Final Fantasy IV, completely worth it and I still have it. My parents were mad that it was $40 used.

I didn’t sell many games back, but for some reason, I sold that same game store Mega Man V for Game Boy complete-in-box, probably for a pittance.

https://en.wikipedia.org/wiki/Z_(video_game) Worth it, played the hell out of it. Though I’m not sure if I ever beat it.

Metroid Fusion. Such an awesomely replayable game.