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Jurassic War -- maybe this isn't a bad game at all, but RTS was never really my thing, at the time I thought "dinosaurs were the shizzle" and that alone made me buy this. Never even got past level 1, and gave the game to a friend that was more of a strategy gamer. He never talked to me about the game, so I'm guessing it's bad even by RTS fans' standards.
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Outcast -- I only learned about this game a few months after joining GOG, and it's a pretty recent purchase. Fans of the game seem to love it and praise it as one of -- or downright *the* -- best game(s) ever made. I looked at the game's GOG page, from the descriptions it sounded like my type of game, and I decided I should buy it. Full price, even. As it turns out, I ended up hating it. Yes, it's revolutionary for its time, and I can certainly praise that, but it doesn't particularly excel at anything it aims at doing. Clunky controls, laughable script, bad voice acting... an impressive voxel engine that I admire as a piece of video game history, but that was outdated by the time the game was released, and a plot that is nothing more than Tintin meets Stargate (the movie). Even though many consider it the grandaddy of sand-box games, I highly doubt it had that much of an impact in the gaming world, as, from my understanding, it was kind of a commercial flop. People would have to have been *influenced* by it for me to consider it the grandaddy of whatever, and I have my doubts the devs of Grand Theft Auto III were major fans of Outcast.
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Shadow Man -- I'm a huge fan of the Legacy of Kain series (especially the brilliant Amy Hennig titles, starting from Soul Reaver; Blood Omen is a great game, but I think it's highly overrated and overhyped, Soul Reaver is definitely the better one, out of the two), and I thought I would enjoy this game, since it seemed similar in themes, world, gameplay and even aesthetics. Well, it's just a mess of a game. If you grew up playing Shadow Man, it's totally understandable for me that you still cherish it, but for newcomers... I wouldn't recommend it.
[EDIT] I would've mentioned
Divine Divinity, but I didn't purchase that one, someone gifted it to me thinking I would like it. To this day, I keep trying to get into it, with no success.