Fallout 2. Had played Fallout before and wanted to play the sequel.

Jagged Alliance & Jagged Alliance: Deadly Games

Got them the day my invite to the sites beta arrived in my inbox and all the prices were just in dollars, both were $9.99.

Dragonsphere, back when it was free.

Saw a message in another forum dedicated to old games about it on GOG and subscribe to get the game. The first game I purchased was Tales of Monkey Island.

Total Annihilation: Kingdoms :)

happy to have played it again and that is the game that got me hooked on wasting a shit load of money on this site hehe

Witcher 1, because I really wanted to play it before the 2nd part came out, which I did and loved. But Ironically I never played part 2.

Baldur's Gate: The original saga. My physical copy had scratches due to careless handling by myself...which meant I never got to see the werewolf island from the expansion :-( So I bought it here and finally, after many years, I played through the werewolf island. Was actually a bit disappointing though.

... No, not Teenagent,.. it was "Beneath a Steel Sky", seriously!

And I failed miserably, because I skipped Interplay's Fallout giveaway, which will never happen again, cause Bethesda's re-release dropped the extras.

I am gonna drag this shame together with me, till I drop:
"You failed to get Fallout. Permanent -1 CH, -3 INT (cause, def, of "failure")"

Might and Magi 1-6, mainly because that was the one major classic WRPG series that I hadn't played before. (Note that, by "classic", I am referring to series that have really old games; for example, Baldur's Gate 1 is too new.)

Well, I hadn't played any of the SSI AD&D games other than Dungeon Hack, but I don't like D&D mechanics that much for CRPGs, and I prefer the other mechanics computer games back in the day used (with some exceptions, of course). Note that this was well before I knew about the sexist rules of 1e AD&D. (I was more familiar with 2e, which had no such rule.)

Still M.A.X. + M.A.X. 2.

I've played the first M.A.X. game somewhat (years after the purchase)... but I don't quite like it. It is a bit too stressful strategy/tactical game to my taste, playing it feels like an uphill battle all the time. I don't get similar enjoyment out of it like from, say, Starcraft or Age of Empires 1-2.

The Witcher 2.

Giants: Citizen Kabuto. After being introduced to it by a friend in 2004 I spent years looking for away to buy the game myself, but couldn't find it anywhere until GOG.

I think the first game that I bought was XIII. They had a sale and a James Bond style spy game with comic book aesthetics in the way Archer was made just appealed to me a whole lot.

Blake Stone: Aliens on Gold from JAM Software - the very best game made on Wolf3D engine. For some reason it was not pirated that well in Russia like other FPS games: either it was a shareware vesion or a password protected game without a proper crack. And i always dreamed to buy this game some day along with the sequel and finish it for good. Well, good old games made my dream true! That was my third game and first game i purchased on GOG.

The very first game was freeware Lure of the Temptress which i didn't like much. And the very second was another freeware Beneath a Steel Sky which was the best point&click adventure in my life. I heard so much good things about Beneath a Steel Sky and then suddenly GOG gave it to me for free. What a happy man i was ;)

Amnesia: The Dark Descent

On the first Insomnia sale, I was looking for good games compatible with a mac.
Still the first game I played was The Witcher 1... I actually played Amnesia later on, it was not the second (King's Bounty the legend) or the thrird (the witcher 2).

My first game was Fallout, when it was given away for free. Now I have 407 games on GOG. Well played, GOG.