Persona 2. Trust me.

Depends on the tone you want in story earlier games for darker later for more lighthearted

Have you played P3 or P4?

Any of them from P2 to P4, the first one isn't that great in all honesty

Persona 2 is certainly a great game, but it and P1 are completely different from 3-5. If you want an experience similar to 5, go for either for 4 or 3. Although if you want a more hardcore experience that's more similar to Shin Megami Tensei, the franchise persona was born from, you'd want to try 1 or 2.

To add onto what Jun is saying:
Persona 2 carries on the darker tone P5 carries, as well as has demon negotiations, so you'll feel at home.
It remove the schoolboy theme, and social stats, and replaces it where your whole team is a wildcard user, and it's more of a classic RPG.
I've only played Innocent Sin, but a lot of people swear by Eternal Punishment.
Persona 2 IS is the first half. EP is the game's second half of the story.

Hmmm, I definitely want to go for a darker tone while sticking somewhat to 5. Sounds like a toss up between 2 and 3.

Do keep in mind that as the games get older the gameplay mechanics change a lot 4 is probably better for dungeons than three I haven't played two but if it's anything like one then it's gameplay changes drastically compared to 3-5

3, 4g are the most similar to 5

3 it is!

>.>
4G is nothing like P5 in terms of being dark.
It's the happiest scooby doo game of death I've ever seen.

First off, I'd like to thank Joker for expanding upon what I said as I know I did leave some info off from my last post. Second, I feel it's important to tell you that 3 and 4 have randomly generated dungeons while 1 and 2 do not, making them more similar to P5 in that aspect.

@Joker 4 is a better game than 3 but yes 3 is darker. But the simple fact is 3 and 4 share more with 5 in terms of similar gameplay than 1 or 2

Lol, nice use of the scooby doo. Yes, it is light-hearted but I think it's funny that way for a game about murder. So yes, scooby doo exactly hits the mark of what it is.

I would have gotten away with it too if it weren't for you meddling kids can be used to sum up 3 and 5 though too..

You'd really be missing out if you skip 4 though

I have a feeling I'm going to play 4 right after 3

Yeah, 4 is a must play. It's a really good game. It's just the most light-hearted one in the series. But, that in no way takes away from the fact that the characters and story are good.

4 and 3 are also more elaborated upon outside their original games I.e. P4 the animation p4 arena which expands on three as well p4 DAN etc

Like everyone said, P3 and P4 are very similar in gameplay so it's good to play them back to back. After that, I recommend going to P2.

How big is the system shock with the OG games? I literally know nothing about Shin Tegami Tensei