I've got my first PC back in 1997. and two PC games I've played first were Broken Sword II and Tomb Raider 2. In each of them I was stuck so many times because I was a total newbie. Plus, I didn't have an internet connection back then, so I couldn't consult any walkthrough.
But the two most difficult games I've played so far are probably Hitman 2: Silent Assassin and Commandos 2: Men of Courage. When it comes to Hitman, I'm a huge fan of the complete series, and each of the games is difficult and challenging in it's own way (that is, if you play them like you should - silently). But Silent Assassin is IMO the hardest so far, because of very harsh AI response. So completing the missions with the highest rank is not an easy job.
The same goes for the Commandos series (minus Commandos Strike Force). Although Commandos 2 is my favourite installment in the series and it's notoriously difficult, now I think that the first ones are even harder. I've started playing them a few days ago (never played them so far) and was suprised how tough they are, even to me who played Commandos 2 & 3 many times before. Maybe this is the reason, because many things you can do in the later games weren't yet introduced in the first two, so it's difficult to accustom to this.
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