With my own money, it would have been some ZX Spectrum budget title. I clearly remember Fantasy World Dizzy being mine and I think I bought it with my own money rather than it being purchased for me, so I'm going to go with that.
Games

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It was either Lost World: Jurassic Park, or Williams Arcade's Greatest Hits for the Game.com. I think I was the only kid in the world who had a game.com lol
Space Quest IV: Roger Wilco and the Time Rippers.
The 3.5" floppy version for PC.
In a box, off the shelf at Kmart.
Must have been Gran Turismo 3, during those days I was switching from pocket money to spending my own income so it's not sure if GT3 was still a gift and GT4 was actually my first self bought game.
I do remember i owned the platinum edition of GT3 and GT4 was bought at release.
It was definitely worth it, Up until today I still dream about owning a race sim setup to do some serious racing and developing my skill. But I never got past a used Logitech G29 mounted to a desk and a chair that kept rolling away from the pedals type of setup.
I had a fairly long term of being unemployed during Covid which ended up in me buying that G29 as I spent a lot of time playing GT sport and finally for the first time ever got all gold on the licenses, so I knew I was making some good progress from all the time spent.
I even dared to try online racing and as I got better slowly managed to hold myself among others, which made me happy.
Tales of Symphonia, GameCube.
Final Fantasy 7 for the PS1.
Secret of Mana. I was 12, and went and worked under the table stripping tobacco. The game was well worth what I paid, the job wasn't.
Secret of Mana is responsible for one of my earliest memories (gaming or otherwise) where my dad had given me a controller and convinced me I was playing with him. I dont know how long he got away with that because the memory is me slowly figuring out it means nothing.
Well that was a shit thing for him to do. One of the reasons I got the game is that my younger brother was 9 and youngest was 4. I also got a third controller and the 4 controller adapter.
I played Poppoi, younger bro got Marle, and youngest bro was given the sword boy and told where to go. Younger bro got quite good as the healer.
The three of us got all the spells to level 8:99, and yes, I do mean ALL. We also got all the extra weapon orbs out of the Mana Fortress, though I found out later that we did miss some really nice weapon and armor drops before the thing takes off.
I dont remember which I bought for myself first since I used to raid gamestop regularly in high school but I remember my cool aunt taking me to gamestop when I was a kid and I asked her to get me Metroid Prime 2 and that shit was excellent
Some Atari ST game, not sure which. Maybe Spacola? Early teens.
First game I ever bought myself was also a console. Bought a Jaguar with DOOM, even had the insert on the controller for all the weapons. Was totally worth it because it was bitchin'. Bought it from a car boot sale with my pocket money for £5.
Didnt last long because I melted it by trying to use the SNES power pack with it. I was about 7 so things like amps and watts didnt feature into my reasoning. Plug fit, plug works, its fine. And it was for about 5 minutes until it started smoking.
I lived in a pretty rural town at the time. This was the best game zcmi had for our brand new 386. World Gamee
Left 4 dead 1&2, I was early 20's, and I arrived to gaming late in life. Was it worth it? Yeah, I was pretty addicted to zombie shit back in the day. XD I only played the campaigns tho, wasn't confident in my ability to play with others.
I'm pretty sure it was Jedi Knight: Dark Forces II. I don't actually remember buying it and might have played Warcraft 2 beforehand, but I spent many ... Many happy hours on DF2. One of those two was my introduction to multiplayer gaming, but for sure I spent a lot more time on DF2.
As for whether it was worth it, it arguably shaped a lot of my life to date. Also I met at least one friend whom I still talk to (though rarely) to this day. I would say yes.
It’s been a long time ago….
For a console: probably https://en.wikipedia.org/wiki/Kaboom!_(video_game)
For a computer: for my C64 https://en.wikipedia.org/wiki/Ultima_IV%3A_Quest_of_the_Avatar
Just Cause 2
I was 13 and wanted to play it with my friend. God that was awful.
Baldur's Gate 2. The manual was so good, and the map. You'd pay $200 for some kind of special edition for that quality these days. Totally worth it.
Two answers to this question.
The first game that my parents bought for me was Wing Commander from a garage sale when I was like six.
The first game I bought on my own was Freelancer when I was around fifteen via eBay.
Both were totally worth it.
Sid Meier's Civ 5, and I was 24 😆 (growing up, my family was piracy-only, so this was the first game I actually bought)
and was absolutely worth it :) I paid ~15 GBP for the base game + some expansions and DLC, and so far put 500+ hours into the game. I still reinstall it every few years.
I think it was the GameCube version of Sims 2. I remember going with a friend to get it to play before another friend came over for a sleepover. We loved Sims Bustin Out when I rented it from Blockbuster, but figured Sims 2 was even better cause....I mean it has a number in the title so it was probably the sequel to Bustin Out. I also remember being extremely nervous cause it was rated T and I was like 11 or something.
It was a game for the C64 and I was 12, but I am not sure what game it was. Such a long time ago.
I really think it was that set of three games, Half Life, Portal, and whatever the other one was. The orange box was it?
Where did I get that first xbox 360? I think it was given to me or traded... I dont remember, but I think I went out and got Portal as my first ever game purchase.
we had games and consoles before that, but I didnt buy them.
I think my buddy back then, got the ring of death, and he got it fixed through the mail. They sent him two xboxes on accident, so he gave me the extra one. I think thats how I got it.
I def remmeber going to game stop to make the game purchas though, I was giddy with excitement
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
Pokemon Blue. I saved up then learned about sales tax at the cashier, so my dad bailed me out with the extra $5
King.
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.
Starcraft
Same. Was playing custom maps with a 33k modem. Oh the memories...
The first game I ever bought with my own money was Metal Gear Solid 1. And the PS1 to play it on.
I wanted FF7 but they didn't have it. But MGS was a good second choice. It was also the first time ever buying anything from a second-hand store. I wish I could remember the name of the store; it wasn't Funcoland or EB. They had a logo that was an anthropomorphic SNES cart, tho.
Rise of the Triads. It was not worth it because there was a fault on the 5th floppy disk so it never worked and I couldn't bring it back to the store because I was 13 and wasn't supposed to be buying violent games but I bought it without telling my parents. So I couldn't take it back without them finding out.
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.
I think it was either Soleil or Dune 2 for the Mega Drive/Genesis. I was 10 or 11 at the time.
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.
This might not actually be the first one, but one of the earliest games I definitely remember actually buying with my own money was Geoff Crammond's Grand Prix 2. I would have been around 7 or so.
Definitely worth it, great game and the demos on the CD introduced me to Transport Tycoon, and the XCom and Worms franchises - and things kind of snowballed from there!
With my own money: Link to the Past. Most definitely.
Crash bandicoot 3.
Considering how uninformed I was back then, it was a hell of a success.
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.
You’ve gotten my curiosity with this RPG I’m going to dig into this!
Thanks for the story and info