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Long story short 2008 was my first purchase here, was total inhalation kingdoms, had all my games transferred over to my new account in 2012 cause I did not know you can change damn user names lol.... ever since I purchased over 517ish games and it has never ended.
Descent 1 & 2, baby! ;)

Funnily enough, I hadn't bought any other games until about a year later - Pro Pinball Big Race USA/Fantastic Journey + Settlers 2 - but I really only started buying on a more frequent basis in the Fall of 2010, so roughly ten years then. Biggest reason for that was due to me being wary of this at the time still relatively new online shop with no knowledge of how long it might be sticking around.

I can't be bothered to calculate the total amount spent since it'd take too long to add all that up, but I wouldn't be surprised if it was well above $3k (if not 4).
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F1ach: I played Obscure on...maybe the first Xbox? Cool game.
Oh heck it was!
The Kingpin remaster looks cool to me. Love that game!
First purchase was on February 13, 2009 and I got Colin McRae Rally 2005 and Screamer.

Still one of my best and most enjoyed purchases here, even though it has been quite some years since I last played them both.
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F1ach: I played Obscure on...maybe the first Xbox? Cool game.
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victorchopin: Oh heck it was!
The Kingpin remaster looks cool to me. Love that game!
I thought the video was the original gfx?
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victorchopin: Oh heck it was!
The Kingpin remaster looks cool to me. Love that game!
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F1ach: I thought the video was the original gfx?
This one's more up to it! :)
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F1ach: I thought the video was the original gfx?
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victorchopin: This one's more up to it! :)
Yes much better, would love to see in-game footage though...the music was great, nice hearing it again!
Looks like I'm one of the oldest posters here, alongside thraxman and Mr.Mumbles. First purchase was Sacred Gold on Nov 11, 2008, followed a month later by Gothic and Arx Fatalis. Currently at 337 games purchased, and I'm not going to count up what I've spent, as I'll either end up having to re-evaluate my spending priorities, or feel like I've ripped off GOG given the amount of entertainment they've provided me.

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Crosmando: So what was early GOG community like? As in the first few years.
It was a very... focused community, with most of the early members being a combination of folks who's grown up through the 80s with classic games, and those having a major axe to grind with DRM (at the time DRM was pretty ubiquitous and it was also quite difficult to get functional versions of older games). For the first few years it was a pretty small community with a dedicated group of regular posters who were actually a pretty cool group to converse with regularly. The release of The Witcher 2 in 2011 was essentially the Eternal September for the early GOG community, resulting in an explosion of new members. The fake shutdown publicity stunt in Sep 2010 also drove off quite a few community regulars, and the combination of those two events resulted in a pretty significant shift in the GOG community (changing from a small, insular core to a wider but less regular community). For those who aren't aware, The Witcher 2 actually contains a reference to the fake shutdown fiasco and the following GOG apology.

I actually had a chance to meet some of the key GOG people in-person at a meetup during the GDC in 2014, which included founder and CEO Marcin Iwiński, as well as a well-known community manager at the time with a distinctive hat. A lot of us were pretty awkward nerds at the time, but it was still really neat to meet many of the key people who had made GOG happen and drove quite a change in game distribution at the time (before GOG pretty much nobody was interested in distributing older games, and DRM was just regarded as a standard part of game releases that wasn't going to change).
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DarrkPhoenix: Looks like I'm one of the oldest posters here, alongside thraxman and Mr.Mumbles. First purchase was Sacred Gold on Nov 11, 2008, followed a month later by Gothic and Arx Fatalis. Currently at 337 games purchased, and I'm not going to count up what I've spent, as I'll either end up having to re-evaluate my spending priorities, or feel like I've ripped off GOG given the amount of entertainment they've provided me.

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Crosmando: So what was early GOG community like? As in the first few years.
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DarrkPhoenix: It was a very... focused community, with most of the early members being a combination of folks who's grown up through the 80s with classic games, and those having a major axe to grind with DRM (at the time DRM was pretty ubiquitous and it was also quite difficult to get functional versions of older games). For the first few years it was a pretty small community with a dedicated group of regular posters who were actually a pretty cool group to converse with regularly. The release of The Witcher 2 in 2011 was essentially the Eternal September for the early GOG community, resulting in an explosion of new members. The fake shutdown publicity stunt in Sep 2010 also drove off quite a few community regulars, and the combination of those two events resulted in a pretty significant shift in the GOG community (changing from a small, insular core to a wider but less regular community). For those who aren't aware, The Witcher 2 actually contains a reference to the fake shutdown fiasco and the following GOG apology.

I actually had a chance to meet some of the key GOG people in-person at a meetup during the GDC in 2014, which included founder and CEO Marcin Iwiński, as well as a well-known community manager at the time with a distinctive hat. A lot of us were pretty awkward nerds at the time, but it was still really neat to meet many of the key people who had made GOG happen and drove quite a change in game distribution at the time (before GOG pretty much nobody was interested in distributing older games, and DRM was just regarded as a standard part of game releases that wasn't going to change).
I remember the fake shutdown. I had just been burned by both STEAM and Stardock. I purchased my first game here and the next day I came here to download the game and found the shutdown notice. I was like, "Figures!"
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DarrkPhoenix: […] before GOG pretty much nobody was interested in distributing older games, and DRM was just regarded as a standard part of game releases that wasn't going to change […].
This is not to be underestimated.

Whatever happens in the future, Gog created a counter-narrative —— at least for a little while —— to support the individual against the prevailing corporate authoritarianism, which seemed to hold the gamer as a necessary evil to be dealt with in order to get their bank details.

It's an idle thought experiment, but imagine how much better gaming might be without the constraints of DRM. What exciting developments might have transpired if all that money and effort went into gaming, rather than authentication means & services.

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Edit:

Another, inescapable comparison this conversation forced me to make when I reviewed my first purchases was the huge increase in cost for games. If Deus Ex is worth less than a fiver, why would I pay triple or even TWENTY times that for a modern, lesser one?
Post edited September 19, 2020 by scientiae
First game I added to my library was Flight of the Amazon Queen.

First game I bought was Civilization IV.
My first purchase was The Witcher: Enhanced Edition Director's Cut, on July 4th, 2014. (This is ignoring the 7 free games that were auto-added to every newly-created account at that time.) I had been looking for a version of Morrowind (physical or downloadable) that I could confirm was DRM/client-free, But eventually gave up and got The Witcher instead. It was the first downloadable game I ever purchased (having just gotten back into the PC scene a half-year earlier), and remains one of only two DD games for which I've ever paid the full price (at the time). (Had I known just how often GOG put it on sale, I probably would've waited, but I can't say I didn't get my ten bucks' worth.)


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DreamedArtist: Long story short 2008 was my first purchase here, was total inhalation kingdoms, [...]
I've heard that game is breathtaking.