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Outcast brought me here, I accidentally found it on youtube and wanted to know wether it'll work on xp so I googled for it and GOG was one of the first pages that appeared, I knew I had seen GOG many times before because I'm constantly looking for old games to enjoy and the idea of running Outcast without any compatiblilty problems finally paved my way to GOG.
that's funny because even though I often saw GOG I had no idea what it was about and I never took the time to look it up because I always was sceptical towards digital distribution and gamestop, flea markets and saturn etc were the only places I bought games, but the troubles I had with running some games finally made me take the plunge in a completely new territory.
And I didn't regret it, I still prefer buying games which will work without problems, or have patches to make them working, physically in the store because I like filling up the shelves in my room more than the shelves on the internet, but for all the other games (and those are a lot, too) this is a wonderful place to be and the community is incredibly friendly ^.^
Freespace and Fallout series games.

I stayed for the Settlers2 (original), though!
Instabought the D&D classics almost as soon as they appeared here, too ^_^
Even plumped for a few of the newer, Indie releases. JJust because DRM-Free <3
Heroes Chronicles - only place on the internet to buy it.
Heroes III. I had two original CDs and both blew up in cd rom. So, i bought it here :D
Interstate '76, but it was DRM-free that made me stay.
None, but I was told there would be punch and pie.
I think it was Earth 2150. Back in April 2009. Some time after I bought Unreal Tournament 2003 and then I took quite a time before I started to buy here big time.
i think like many in the very early going, it was fallout.
Neverwinter Night 1 and 2. And 140 or so games later, my wallet is still screaming.
Not so much a game, but more the news that GOG was going to be DRM-free. I'd refused to buy anything digitally distributed up until that point.
The ultima series, then I found out that Ultima IV was free.Then I see all these great games like Neverwinter Nights 2.
So, here I am!
Duke Nukem 3D Atomic Edition. I had Duke Nukem 3D already but found myself in need of the Atomic Edition for Duke it Out in DC as well as the DS source port. The Eduke website has an ad for this site and there you have it.
Total Annihilation, Total Annihilation - Kingdoms and Heroes of Might and Magic III brought me here.
King of Dragon Pass. I have heard of that game many times, but it is pretty rare and expensive, so I didn't keep attention of it for a while. The Torment Tides of Numenera Kickstarter and especially the Georges Ziets interview (maybe it was the RPGCodex one, I am not sure) made me thinking of it once more, and while I had heard of GOG for years, I haven't purchased many digital games until I bought KoDP here (only The Secret of Monkey Island Special Edition on Steam at release and that's all).
I really wanted to play Planescape: Torment, as I had heard so much about it, and lo and behold here it was DRM free and for only $10. The site has grown so much since then and is now my go to site for both new games and classics!