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[Rince Wind]

XCOM: TftD - I played the unreasonably hard demo and always lost. But those pedia screens after the loss hooked me. I didn't know it was the 2nd one back then. Only other game with a pedia I knew was
Civilization  - I didn't know what I was doing (ok, more childhood than teenage years) and never built any buildings, because having to lower the research rate to pay for them is bad, right? After a while I knew the tech tree by heart, so I could beat the copy protection.
I played a bit of X-Wing, but with only mouse and keyboard it was too hard. I tried
Tie Fighter - at a friends PC and was blown away. Once I could get my hands on a joystick I barely played anything else for quite a while.
Bundesliga Manager Professional - local multiplayer, I never cared for football, but it was a fun management game, especially with friends.

The first two games I payed full price for were
Alpha Centauri and
Jagged Alliance 2
and I played them so much my grades suffered.

[Zangi]

Chrono Trigger
Romance of the Three Kingdoms 4(I massively sucked at this game, but still put hours into it.)

A bit later then that would be the era of Diablo 1/2 and Starcraft, with MMOs like Lineage 1/2 and Ragnarok.

[Vicomt]

Repton (BBC Micro)
Elite (BBC Micro)
Descent (PC)
Wolfenstein 3D (PC)
Hexen (PC)
Heretic (PC)
Duke Nukem 3D (PC)
Doom (all of them) (PC)
Quake (all of them) (PC)
Unreal (all of them) (PC)

there's a few more, but those are the ones I remember after 30+ years
Elite was a literal gamechanger, and that 3d wireframe was what made me realise computers were where I wanted to be.

[LoSboccacc]

childhood probably monkey island, sim city and sensible soccer. definitly played games before and after, but these formed the core of my memories back then

teenage days it was probably total annihilation, carmageddon and black and white I played the most. duke nukem was my first multiplayer experience, so there's that.

I discovered many cult games from that era way later, I was already at uni for example when playing xcom for the first time.

[deoloth]

Black and White (1&2)
Star Trek Birth of the Federation (Good 4x game)
Romance of the Three Kingdoms 7.
MechWarrior 2 Mercenaries
Xcom UFO Defense.

Though the first Half-life and Unreal Tournament were the first ones that got me introduced the delight of early game mods. From that sorcery mod from unreal tournament whose name I don't remember to to halflife mods such as Science and Industry and Sven coop... frankly they had a much larger influence then the base games did on me.

Honorable mention would be Xwing Alliance. Played the previous and they were good but I really enjoyed the story of X-alliance and the concept of starting as a pilot for a family run trading company.

[crazyabe]

Childhood:
  Diablo 2
  Zax: The Alien Hunter ~ I'm pretty sure this and Diablo 2 are the only games on this list I can claim to have "won"
  Nox
  Baldur's gate
  Fallout (1/2) ~ I remember proudly telling my parents that I had killed *everyone* in one of them, they may have been concerned since I remember them taking my character from location to location looking for NPCs before finally putting the CD on a higher shelf
  Starcraft (original)
  Warcraft (1/2)
  Sly Cooper (1/2/3)
  [Microsoft] Paint ~ I'm pretty sure I spent a combined total of 2-3 years of my childhood having the time of my life poking at pixels
Teenage years
  Minecraft (Xbox360 edition demo)
  Supreme Commander (1/2)
  Overlord (1/2)
  Starcraft (Broodwar)
  Dwarf Fortress
  Rimworld (Pirated (A17/B18))
  Nox (Pirated)
  The Last Stand - Dead Zone

[LASD]

Weirdly, the only game that popped into my mind when I read the thread title is Creatures 3. Aside from Dwarf Fortress, I don't think any game has left as big an impression on me.

Anything that embraces the chaotic mess of biology and life in general has always been so captivating to me.

[Akura]

I remember having a lot of fun with Power Stone and its sequel. And I recently learned that both games will be part of Capcom Fighting Collection 2 being released on both Switch and Steam next year.

[Iceblaster]

Robotech Battlecry and Invasion are games that really Got Me as a kid, and while I never could beat Battlecry, I beat Invasion multiple times. It's a very 5/10 game and is kinda jank but it's got that mid 2000's FPS/TPS gameplay that just vibes with me.

[MonkeyHead]

Oh boy did I have some, uh, odd ones. As a Sega kid who backed the wrong horse with the Sega CD and Saturn, I had a limited choice.

Sonic CD, the best in the series.
Road Rash 2. Fighting on motorcycles? yes.
ToeJam and Earl. This actually got me into rougelikes.
Cannon Fodder. Still hurts to lose Jools, Jops, and Stoo.
Mega-lo-Mania. Odd god game that actually got me into all forms of strategy game.
Virtua Fighter. Square polygons could have been the future.
Theme Park. My spicy brain loved optimising the pathing to force coffee shop purches.
Lemmings. Oh god the music.
Speedball 2. Good old hyper violent future sport.
Soviet Strike. I have an unusual knack of identifying Russian mil gear thanks to this.
Civ 2. Gamebreaking Dragoons.
Sim City 2000. YOU CAN NOT CUT FUNDING.
Alien Trilogy. God that was hard.