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I have all of Ultima games but didn't actually play any of them. I was a big fan of Ultima Online back in time and I am looking for that Ultima game which reflects UO the most. I mean - the world, cities, map layout, story, etc.

As such it looks like Ultima VII is closest candidate for such a game, but I have heard that previous Ultima games were much better.
From what I have played:

Ultima 1: Very simple game. Can be harsh at first, especially with 0 Food = game over, but it is interesting. One interesting mechanical quirk is that there is no max HP stat: You simply buy HP or earn some on leaving a dungeon, and there's no healing in the usual sense. There is a mandatory action mini game near the end, however.

Ultima 2: Haven't played, but from what I hear, it's the worst of the early Ultimas.

Ultima 3: First Ultima with a party, and the one with the best class system. What I like is that spells only need MP, which regenerates on its own. (Earlier games you buy individual casts of spells, while later games require reagents.)

Ultima 4: Introduces the modern map of Britannia, which makes the world map quite vast in comparison to earlier entries. Unfortunately, also introduces the need for reagents to cast spells, even basic ones. To beat the game, you must better yourself in the 8 virtues, which means you need to avoid doing things like stealing. It's worth noting that the two console ports (NES and SMS) of this particular Ultima game are the best console ports of the entire series, and they are quite different from one another. One flaw is that the game becomes more cumbersome when you recruit companions, and you can't get the ending unless you've recruited everyone. This game introduces dungeon rooms, which are my favorite new mechanic in the game.

Ultima 5: Much darker tone than Ultima 4. Introduces things like a day/night cycle (with it being dark at night) and ammo management for bows (but the strongest ranged weapon doesn't need ammo) and has the Underworld, a vast map the same size of the overworld, but harder to navigate. The Shadowlords, which randomly move between cities at midnight, can be annoying. Also, to level up, you must rest and hope that Lord British appears. On the other hand, you can mix multiple copies of a spell at once, and you can enter solo mode during battle so you only need to worry about controlling one character (useful in dungeon rooms after you've killed the enemies).

Ultima 6: Major change. There are no longer separate screens for the world map and towns, and no separate battle screens. No more first person dungeons. Unfortunately, you have to manage each character's inventory separately and there is a weight limit. On the other hand, at least you can control level ups, you no longer need to mix spells in advance (but you still need reagents), and food is only consumed when you rest. Note that the world is essentially persistent; if you kill an NPC, she will not come back when you leave the area. Also, there are many exploits in the engine (like magically locking an already locked door to overwrite the previous lock). Furthermore, only the Avatar is a good spellcaster, though there are a few companions with extremely limited magic abilities.

Ultima 7: Switches from turn based to real time, and the game is worse off as a result. Also, only the Avatar can be controlled, and only the Avatar gets access to magic.

In any case, Ultima 4 is the first Ultima whose world map is likely to resemble Ultima Online. I should point out that Serpent Isle and Ultima 8 do not take place in Britannia.
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dtgreene: <snip>
Hmmm, looks like each game has its pros and cons. Ultima 4/5 look like the games to try. Do they feature any kind of respawn or do they work like Ultima 6/7 in this regard?

Where does Ultima 8 take place? UO also wasn't limited by Britannia, it had Ilshenar added later on as well as Malas and some other facets. Though I must say that Britannia was the most detailed facet.
Post edited December 15, 2016 by Sarisio
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dtgreene: <snip>
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Sarisio: Hmmm, looks like each game has its pros and cons. Ultima 4/5 look like the games to try. Do they feature any kind of respawn or do they work like Ultima 6/7 in this regard?

Where does Ultima 8 take place? UO also wasn't limited by Britannia, it had Ilshenar added later on as well as Malas and some other facets. Though I must say that Britannia was the most detailed facet.
Ultima 4 and 5 do not keep long-term track of whether you have killed an NPC, so if you leave and return, the NPC will be back. Similarly, chests also respawn when you leave and come back (in Ultima 5, you can steal some nice treasures from the castle repeatedly).

Just be aware that stealing chests and killing innocent townspeople isn't considered virtuous, and will hurt your virtues in Ultima 4 (and you need them maxed to become an Avatar and beat the game) and your karma in Ultima 5 (which affects how much XP you lose when revived). (In Ultima 3 and earlier, there are no long-term repercussions for such acts, and in Ultima 1 and 2, you sometimes have to do such things.)

In Ultima 6/7, townspeople and NPCs stay dead; however, in the wilderness and dungeons, random monsters will spawn without limit.
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dtgreene: <snip>
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Sarisio: Hmmm, looks like each game has its pros and cons. Ultima 4/5 look like the games to try. Do they feature any kind of respawn or do they work like Ultima 6/7 in this regard?

Where does Ultima 8 take place? UO also wasn't limited by Britannia, it had Ilshenar added later on as well as Malas and some other facets. Though I must say that Britannia was the most detailed facet.
Ultima 8 takes place on 'Pagan' an entirely different world that had been reduced to a single island. It is the first single character game since 2 and much more 'actiony' (no party, real time combat though with only a few monster types, lot of platform jumping). 9 shares the single character aspect and while it returns to Britannia the rushed nature of the game and story rewrites leaves one feeling like it often isn't the Britannia they remember.
UO... My all time favourite, wasted most of my precious years on that game, lol. Anyway, the closest one is Ultima 7, it has the full map, excluding T2A and Ilshenar ofc. If you install the fan made remake you'll get a game witch comes very close to the UO look and feel.

Cheers, Alex
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Alex_Mars: UO... My all time favourite,
Not Age of Wonders?
Even Garriot himself considers Ultima VII to be his best title. Just don't be confused by all the subtitles; The Black Gate is the one you want. Serpent Isle is sort of Ultima VII.5, but is much more linear, shows pacing issues, and appears to lose its polish near the end.

Ultima VII, however, is the best in open-world from the early days of gaming. It's also very consistent, intuitive, well-written, with lots to do apart from the main quest. The graphics are also very good, particularly with Exult.
Here's one point in favor of Ultima 3:

Ultima 3 has more races, classes, and genders than any other game in the series (though it *might* be tied with 2 for races; I'm not sure about this).

Here are some details:

Races: Ultma 3 has 5 races to choose from. 4 and onward got rid of the race selection, so there's only one race at that point.

Classes: Ultima 3 has 11 classes, and there was some attempt made to balance them. Ultima 4 has only 8, and they're not as well balanced. (I can excuse Shepherd being weak, but why can't Fighters use any of the magical ranged weapons?) Ultima 5 has only 4, and the main character's class is always Avatar. Ultima 6 has only 3 classes among recruitable characters (there are no mage companions, and Jaana (Druid in 4 and Mage in 5) lacks any spellcasting ability, a discrepancy that is never explained), and Ultima 7 has 2 (the Avatar that can cast spells, and everyone else who can't).

Genders: Ultima 3 has 3 (try pressing 'O' when asked for a character's sex). Ultima 4 dropped the Other option, leaving you with only 2 choices. Ultima 8 further dropped the female option, with male being the only option here (and I consider this change to be a dealbreaker for me).
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dtgreene: Ultima 2: Haven't played, but from what I hear, it's the worst of the early Ultimas.
Can confirm. There are four classes, but one of them (Thief) is for masochists only. Two genders, and gender does matter in terms of starting stat bonuses.

Everything is expensive; spells must be bought, and can only be used in dungeons... but the key item you're searching for can also be randomly dropped by enemy thieves, making both spellcaster classes pretty much useless as well.

There is A LOT of early and midgame grinding, including earning enough to pay for stat increases (and spells, if you go that route); and the game is often unclear about what you have to do next. If you insist on playing it, I strongly recommend a walkthrough for this one.
Post edited December 15, 2016 by TwoHandedSword
Someone without nostalgia has the enviable ability to objectively judge each game according to its merits. Like many people, I prefer the middle games, Ultima IV through Ultima VII. If you start with Ultima IV, it will introduce the story of the Avatar, the ultimate embodiment of virtue. It's a reboot of the series in some ways. The earlier Ultima games allow you to play as an evil character and are more oriented toward hack and slash. Ultima VII introduces many modern gameplay elements, such as dialogue trees, real-time combat, and companions who chat with you. If you can't get into the earlier games, Ultima VII is a good one to try. The later games, well, they were made when EA controlled the property, and many older fans resent that. Without being blinded by nostalgia, you have a better chance of appreciating Ultima VIII.

Ultima Underworld is mostly separate. You'll want to try that eventually, but it's more like the Elder Scrolls series.
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krachtm: The earlier Ultima games allow you to play as an evil character.
Actually, in Ultima 4 and 5 it pays to be evil in the short term. For example, in Ultima 4, for the cost of virtue (which you don't need until later and can be farmed in various ways), you can easily get 99 of all the basic reagents for a total of only 6 gold; you can make up for it later when gold is less of an issue. In Ultima 5, stealing from the basement of Lord British's castle is *extremely* profitable early in the game, and you can regain karma with a series of 1gp donations.

In other words, evil is rewarding, as long as you make up for it afterwords.

Also, Ultima 4 has an item that can wipe out the population of an entire village, and Ultimas 6 and 7 have a spell that wipes out the population of the entire *world*. (Ultima 8 has a similar spell, but it also has the unfortunate effect of also killing the caster, giving you a game over.)
My personal favorites are 6, 7 (complete) and 8. I know that people have their reasoning for liking the older ones, and I do understand that the worlds are bigger in those, and for anyone that played them when they came out, nothing else could recreate that experience.

However, 6, 7, and 8 had amazing soundtracks, beautiful visuals (even today the art style is very interesting) a lot of depth and more fleshed out stories, and their atmosphere (the sum of all these parts) just pulls one in. (In my case anyway) I actually had seen and played the earlier ones a bit, but they never really got my full attention way back then. The one that finally really pulled me in was Pagan. The music alone set a dark and atmospheric tone, the down-trodden citizens eerie locations, interesting magic (if a bit awkward to cast in some cases) etc. were really a good introduction to Ulima for someone that hadn't played any. Each weapon in the game has an in-depth back story, there is plenty of history to the world of Pagan, lot's of books, etc. I hadn't played something so in depth (well, aside from System Shock which I played sometime around then.)

I played 7 afterwards, and it was my real introduction to Britania, and the more classic setting of Ultima. 7 also has a wonderful soundtrack, the party system, a lot of really fun secrets to discover, etc. This was my inspiration for playing more, which ended up being 6. 6 is like a mix between the modern and classic interfaces, and while a bit more primitive, had the same impact on me as 7.

Also, while it's no 6, 7, 8, and while it has many many shortcomings, if you patch it up, add the community patches, replace the speech with text (another patch) and can tolerate a some major differences, Ascension is actually a pretty good game all on its own. Is it a good finish to the series? No, absolutely not. Is it a good Ultima game? Yes and No. It has nowhere near the scale of the earlier games, but it does have a half-decent story, if a bit truncated, great soundtrack again, some very interesting locations, secrets, and some unfinished locations that actually add IMO to the mystery of the game. IMO the game's scale is so much smaller because it was pretty early in the game for expansive RPGs with 3D graphics. I think the switch from 2D to 3D at that time really limited what was possible for a game with the scope of Ultima. (not to mention the artificially set much-to-early release date that the monsters at EA imposed on the devs)

Anyway, I don't think you can really go wrong with an Ultima game, even if you basically play them backwards from the inside out :D like me. As far as feeling at home after playing UO though? Probably 6/7/8.

I have yet to play the Underworlds, but since they're like a mix of System Shock and Ultima, they are definitely on my list of must play games.

Anyway...
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Alex_Mars: UO... My all time favourite,
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PetrusOctavianus: Not Age of Wonders?
Singleplayer or PBM would be AoW, yes. :)

Cheers
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PetrusOctavianus: Not Age of Wonders?
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Alex_Mars: Singleplayer or PBM would be AoW, yes. :)

Cheers
I recall you made some pretty good maps back in the days. :-)