With my own allowance money instead of asking for it as a gift?
Sim City 3000

First game as an adult with a job?
Halo 2

Pitfall by Activision for the Atari 2600. I'm old.

Purchased was Tomb Raider II. So worth it because I loved Indiana Jones.

The first game I ever bought 'by myself' was a sealed copy of Phantasy Star Online for GameCube long after its hayday in like 2011. I worked all summer for it, and it was 200 fucken dollars for an unopened copy. Worth every penny I still have it today, just used the disc to load it into Dolphin.

Orange box, everything before was pirated lol

My older sisters both had several games before I got one for myself. I think the first one that was actually mine wasn’t until Burnout 3 when we got a PS2. All the PS1 games were hand-me-downs.

Colin McRae Rally 2.0 for the PlayStation.

I wanted a PlayStation so much but simply didn’t have the money. I was saving for it.

But bought the game so I could go to my friend’s house and play it on his PlayStation.

Croc

First game I got or first one I bought for my own money? The first game I ever got and played was Super Mario Land for the GameBoy. I remember when the hype around Pokémon Red/Blue coming to Europe was building I was trying to calculate how many weeks of allowance I would need to save up to afford it, so that might have been the first one I actually purchased, I can't remember for sure if I bought it myself or got it as a gift. Diablo 2 launched a year later and I know I bought that one as I vividly remember the car ride back from the store, so otherwise that might be it.

All of these were of course incredibly worth it. I would never have gotten into video games without that GameBoy and Super Mario Land I think, and Pokémon was a formative experience for me as I got to participate in the whole Pokémania phenomenon. And Diablo 2 is one of the games I have the most hours in over my childhood, it kept resurfacing over my school years as me and the other gamers in my school would randomly get the urge to start playing Diablo 2 again randomly almost yearly over the course of like 8 years after its release.

Super smash brothers mele, gamecube

I don't know for sure if it was my money or just my choice, but I went with Strife (1996). I chose it in the store after a long deliberation, my uncle was trying to get me to go with Half Life but I was drawn in by something on the back of the box. PC games used to come in big empty boxes with a lot of art and info on them.

It was unforgettable. Basically if you made an RPG in the old Doom engine with the sensibilities of the nineties and an overly ambitious art department. It was surprisingly well written, and I've been chasing that sense of an expansive, dark yet cartoonish, novelistic RPG ever since.

Can't remember if I purchased it or asked for it, but it is the first game that was just for me on the PC and would have been in my early teens. Wanted it as a computer version of the tabletop Battletech game that I was introduced to by a friend's older brother.

https://en.wikipedia.org/wiki/BattleTech:_The_Crescent_Hawk%27s_Revenge

The play speed was tied to the CPU speed, so when we upgraded the family computer a couple years later all the movement happened at ludicrous speeds! Good thing it was turn based.

BATTLETECH 2019 was like a modern version which was pretty awesome and hit all the nostalgia buttons!

I think it was KotOR 🤔

I have no idea. I was probably 5, and had birthday money.

Pokemon SoulSilver for $20 when I was 8 or 9 years old. I don't have the cartridge or PokeWalker anymore and I weep at the value lost

https://www.lemon64.com/game/skate-crazy

All was pirated, because nobody actually sold games. Some shops specialized in electronics slowly started having random C64 titles. This was one of the first ones I ever saw.

Never had actual original covers on any of my pirated casettes.

Game was shit.