StarCraft's campaign was a masterpiece. I get to include Brood War here too.
RetroGaming
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Since StarCraft and SC2 are free, you should check out SC2:Mass Recall. It's a mid for SC2 that brings in not only the original campaigns, but three other mini campaigns that I have never seen before.
The return of the Obra Dinn. Really fun unique game
I feel its been so long since i last played it might feel new to me, but still it wont be the same as first playthrough.
Portal or Arkham Asylum, something that surprised me in unexpected ways.
Portal because I thought I was getting a neat puzzle game (I was), but GLADoS blew me out of the water.
Arkham Asylum because of how effectively some of the Scarecrow sequences messed with me specifically (making me think my game had glitched, etc.)
Portal 2 and Undertale the true pacifist run
The original Luigi's Mansion. First off little kid me was still scared SHITLESS cause this game has ghosts everywhere. And that dumb kid didn't have a clue what "triangles" or animations" were so in his mind those ghosts could do ANYTHING to poor little Luigi just trying to save his brother.
And the story of course isn't anything super amazing of course, it's a non-rpg Mario game. But again little kid me doesn't know shit. In my mind I can remember thinking "what if E.Gadd is lying and is actually evil. What if I can still find Mario somewhere in this mansion and we can gtfo together.
My family used to rent that shit from Blockbuster all the time and I was youngest of three, so I barely got to play much back then and we wouldn't own it for years. But I can still remember major tears of joy when I finally did and Luigi just starts laughing at Mario with that vent stuck around his neck.
Others for my list that I've seen plenty here so won't gush about the same way is: Dark Souls 1, Both Portal, Destiny if I could experience it from release day and have the shitty content droughts D1 went through constantly, Halo 3, and another I haven't seen is JK: Jedi Outcast
Homeworld
Have you tried a link to the past randomizer . It makes it very fun and you can find different ways to progress through the game . Sometimes you have to do some of the dark world first or find clever ways to get into areas .
Skyrim. After 200 hours, you start becoming really aware of the "seams" and the clunkiness of the Creation Engine. Although, while you're still working your way through the quests, and every stat isn't at 100 yet, it's pure pure pure bliss. To have that original feeling back. Gah!
I agree with lots of what's already been said and haven't got much to add to those extant conversations, so let me try to add in some that I've not seen:
RuneScape is a candidate. I started way back with RS Classic (the sprite-based one!).
Oh, and Dwarf Fortress too. That began in 2009.
Achaea and/or Lusternia are way up there but I don't imagine anyone but me can share the experience.
Oh, as well, Mount & Blade: Warband. Quite the adventure(s).
I don't really game anymore. But this thread did dredge up some memories, old and new.
Thank you.
Dwarf Fortress is one of those games that I love to read about, but I don't think I would actually enjoy playing. Like Eve Online.
I know this is almost a stereotypical answer, but the Witcher 3. because after that game i went and read through all the books. so if i got to re experience it would be the difference of finding siri after 100 hours of gameplay and finding siri after 5000 hours of story. "find siri' is Geralt's primary motivation throughout the books. i can only imagine how satisfying and emotional that scene would feel for the first time with the weight of the books behind it.
Hotel Dusk.
Probably Fallout New Vegas (if that even counts as retro yet). I've played it to death ever since it came out and can't even remember the first time I completed it.
Read dead redemption 1. A masterpiece.
Ghost Trick: Phantom Detective
The story has so many great twists and turns even up to the very end. There was a distinct point about 75% of the way through when I came to the realization that I had to binge the rest of game. Even if it meant I got zero sleep that night, I had to see how it ended.
It was so good I wish I could experience it again blind.
If I were to experience it as I am today (and judge it versus games with modern graphics etc), I'd pick Ori and the Will of the Wisps. It quickly became one of my all-time favourite games, and I finished it three times in a year when I discovered it. Beautiful in so many ways.
Half-Life is probably the game that has had the biggest impact on me, though, so that would be my pick if I experienced it as I did around 1998.
That'd have to be Metroid: Zero Mission and The Legend of Zelda: Wind Waker. Two of some of the only games I actually 100%.
Bioshock. I am sure you can just replay it. The twist at the end... I wish I could relive the surprise again.
Half-Life 2 and Shining in the Darkness.
FF6, FF9 and Links Awakening
Dwarf Fortress was an amazing experience the first few times when you had no idea what to expect or do. My fortress designs have become much more boring (even if efficient) since, and I'm just unable to do the sort of artistic weirdness that happened during the first games.
I have seen no mention of Planescape Torment, so there you go.
Space Invaders
Asteroids
Pitfall