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The interesting thing is pretty much every single Ultima title was just mindblowing when it came out. There’s also “kinda” three series as the gameplay is far different, there’s other games in the “Ultima” series that come later but I’ll stick to the Dos ones here.

The “Ultima Underworld” games are 3d dungeon crawlers, the original System Shock actually uses the UUW 1 engine. Both are amazing, I like the large dungeon in UUW 1 a little better, but 2 improved gameplay and getting to fully explore brittania castle in 3d was cool as hell. If I was forced to pick only one though id pick UUW 1

For the “Mainline” Ultima series, it’s kinda broken into trilogies, 1-3 are the “stranger”‘s first journey’s into sorsaria, they’re a little older and haven’t aged as well as later games but still fun. 4 is probably the most iconic game in the series, Quest of the Avatar, I really can’t praise this game enough, gameplay-wise it’s still aged a bit though, 5 and 6 are good but not nearly as memorable. 7 starts the third “trilogy”, and is the transition to a new graphical style (as a note, the angle is pretty weird, and it’s been shown and had a mod which unfortunately no longer works that rotated the game 45 degrees to the right and that is ALL it took to make it look amazing), 7 also has two parts, the black gate and serpent isle, both are fantastic, it’s easily the best of the final trilogy. 8 is..again…an interesting game in itself (see a pattern here, lol) It improved the graphics and controls considerably from 7, building off it’s strengths. It’s big issue however is this is when EA was taking direct control of Origin so it was rushed and released missing large story chunks, still good but sadly a little anti-climactic in a few things. 9 we don’t talk about.

There’s also two “side story” games, Martian Dreams and Savage Empire, they both use the Ultima 6 engine and are interesting but it’s kinda just “more” U6 but with their own stories (doesn’t take place on the same planet)

If I was put at gunpoint and forced to choose, UUW1, U4, and U7 are the best 3, 1-3 are fantastic games but 4 is where the story gets a LOT better (though the twist in 2 is good) and it otherwise is just an improvment on the first 3 in every way. 7 introduced an entire new type of RPG, with mouse control and the ability to literally pick up ANYTHING in the world and take it/leave it wherever. UUW as you’ve played it you understand how amazing it is, though the walkthrough does kill a good part of the game, it’s really supposed to be a somewhat “open world” exploration game where you make your own path (there’s no “ONE” way to beat UUW)

It’s been kinda a sore spot for me for a long time how forgotten the Ultima series is, it literally DEFINED the computer rpg and everything from Baldurs gate to Dragon Quest used elements pioneered in the series, and every few games they tried new things (the series has everything from first person dungeons, open world maps, and full inventory systems as you go through the games) It was once THE RPG to compare to, but EA’s literally sat on the franchise so long it’s little more than a memory.