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I usually recommend starting with the original Final Fantasy 1 (the PSP version) or IV (either the 3d remake on Steam or the 2d PSP complete collection version).
Final Fantasy 1: A timeless classic, but rather simplistic gameplay.
FF2: A dark, gritty story with tons of bloodshed and innocent body count. They experimented with a Skyrim-like leveling system where instead of XP, every stat and skill and attribute rises the more it's used. This means a lot of grinding to get stronger, but even if you just spend an hour or two at the very start having your party members beat each other up and casting spells on each other to raise their power, the difficulty is a bit unbalanced. You can 1-shot bosses with a Warp spell, only to get curbstomped by the next gang of mooks. Also, exploring the dungeons is pretty frustrating with dead ends and doors that lead into empty trap rooms.
FF3: the last of the true turn-based games. Summon magic and job switching were introduced, but 5 and X-2 did them better. It takes a lot of grinding to max out jobs, which you'll have to do if you're an achievement ♥♥♥♥♥.
FF4 and After Years: The soundtrack is in the top 5 musical score. They replaced simple turn-based gameplay with the ATB system which would be standard for most of the franchise. The story is lovely. The sprite-based PSP version and 3d remake version have some major differences in gameplay mechanics and I like them both, even though the PSP version nerfed Edward back to being ♥♥♥♥♥♥♥ useless. Edward is the main reason Bards have been a punchline in RPGs at large for years. The remake made him strategically powerful, but then the PSP version reverted him to being useless baggage. Also, I hate that the PSP version completely broke Rosa's pray. The 3D version has the augment system which allows for great customization options and strats, but is missing the Interlude chapter.
FF5 is my personal favorite with the job system at it's best and endless ability customization and an incredible story. The steam version is kind of ugly, though, so look up the reshade fix to remove the blur filter.
FF6 is has a slightly better OST (Uematsu's finest work, IMO) than 5, and a brilliant, heart-wretching story. The Steam version is kind of a mess, though. Aside from the blur filter, the mobile-style menus are atrocious.
FF7 is fairly overrated. It's got brilliant story, music and gameplay, but visually has aged horribly and the Steam version has broken DRM that frequently looses your save and prevents it from even running. Only get the Steam version if you're planning to use the 7th Heaven mod manager.
FF8 is really a black sheep. The gameplay mechanics are just plain weird and the story is so convoluted that it would give Hideo Kojima a headache. It's a good game once you get used to it, at any rate. Just get the original version and load it with Roses and Wine.
FF9 is very nearly perfect. Intentionally created as a tribute to the NES/SNES era. The chibi style rubs me the wrong way, but is otherwise brilliant.
X and X-2 are visually stunning, but this is where the emphasis on exploration and discovery starts dying. Things are railroaded a fair bit. The voice acting isn't nearly as bad as some people say, but the poor lip-synching is distracting. The ATB system is retired and things get more hectic with the CTB system of entering actions into a queue.
11 is an MMO. Don't bother.
12 was a rushed mess for the original western release, but everything was fixed with the Zodiac Age remaster. It's the last really worthy entry in the franchise.
13 would have worked okay as it's own original IP, but is basically unrecognizable as a Final Fantasy.
14 is an MMO. Don't bother.
I have not played 15 and have no intention to. "Games as a service" model? Seasonal events? BOOOOOO!
If you do want to buy FF games, consider buying used physical copies so you're not supporting SE. I'll just tell myself you're doing that for my own peace of mind.
III is one of the best because it's turn based, IMO. I hate the ATB system. The CTB is a little better in FFX, but FFX-2 has real time elements when you are switching dress spheres so it's kinda meh.
XV is good since it's TRUE action.........well, action with pause. But, as mentioend above, I don't like how they're trying to milk people. If you wanna buy the base game go for it. It's pretty fun for a while. AMAZING graphics, AMAZING music, AMAZINGly fun gameplay, and a great story.
My favorites would be:
X > XV > VIII > IX > III > everything else
(Emulating) FF1 on PSP or FF5 on GBA is the best choice for a first Final Fantasy game imo. But if you absolutely want to start with a Steam game to play Final Fantasy, personally I recommend XII. The Zodiac Age is a great port and it captures a lot about what makes Final Fantasy good (interesting designs, good soundtrack, expansive worlds, the job system, fantasy races).
But overall it is a decent game.
Only thing that kinda does suck is.. if you want to be a completionist. You have to keep an eye out on bestiary. Because if you miss some monsters on places you cant return too.. then you are screwed and have to start the game all over again. Unless you dont care, and just want that achievement. Then you could always just make save file nr 2 just to get it.
Overall i will say its an overall ok game. Just dont play it forced, play it the way its intended. Only way that is forced that makes sense is the black belt at end of game since that gives you high HP if you keep on using it "if you want to get to hp 9999"
But i say its an alright game. But its not for everyone
FFIII: very simple, basic story (light and darkness). Simple yet charming characters; my first introduction to the job system, turn-based combat (I disliked ATB combat in FFIV), humour, wit, charm, tropes that are present in the FF series [Fat Chocobo] and a fabulous musical score. Again, the music for Fat Chocobo never fails to make me smile.
It does suffer from random enemies, a LOT of random enemies (which is a hallmark of most JRPGs), but does allow you to grind / level. The story is very simple, so do not get expect a narrative experience or memorable characters. The absolute worst aspect is sadly, the final bosses design: you cannot save in dungeons, so first there is an hour or so dungeon crawl, and then a moment of no return i.e. it's do or die (if you fail, back to your save file, losing hours of progress).
Every 1/3 of the time, the game 'decides' that the final bosses are un-killable, and no matter your level, equipment, job, tactics, etc, the game will flat out kill you. Back to your save position, losing hours of progress. I can attest that this happened to me, read up about this online as a forum that I was a member of at the time were doing a 'Let's Play FFIII' play-along, and one of the warnings for any players who wanted to join-in was the final bosses section.
I never finished FFIII for this reason.
FFIV: a much darker and grittier narrative and tone than FFIII. A well-developed story that provides drama, and explores some mature concepts.
The job system makes way for a character narrative as you play the main character [Cecil], and the turn-based battle system sadly makes way for Active Time Battle [ATB] system. ATB is real-time, and different actions take varying amount of time to occur.
FFIV has a much more memorable narrative, strong characters, a good musical score that is appropriate in tone (musical score is a hallmark of the FF series), and retains certain FF tropes and humour, whilst balancing with more emotionally charged scenes.
FFIV retains random enemies, and is a lot more difficult at the start of the game than FFIII.
I would recommend FFIII with serious reservations, and would consider the suggestions to start with FFV (I have yet to play - on my list), and then FFIV (on my list to replay as only played 2/3rds through).
I recommend starting with IV. The game's not terribly long, the story is great, characters have a very fleshed out backstory, and this is one of the few FF games to receive a direct sequel letting you get more of the characters if you love it. As for the version, I'd say GBA > PSP > Pixel Remaster. The Pixel Remaster is missing the bonus dungeons of the first two. The PSP has redesigned artwork that looks nice, but is vastly different than the original.
Yes I know it's not the best place to begin but I needed a casual start and by doing this it also leaves the best part for last. Once I'm done with her I'm gonna get down dirty with FF III-to-XII.
Will probably skip XIV (cause the fever for that online title has worn off) and try out XV and the very first one but we'll see.