NOW if you want to be completely avant garde go for the Digital Devil Saga games! They are a short duology that's very different from both the main series and the other spin offs.
I've also heard Strange Journey is fantastic and it'll probably appeal to you a lot but I haven't played it yet.
Persona 3 and 4 are also excellent choices, very, very endearing characters and story, 3 is more gloomy and 4 more vibrant. You can ignore 5 though, it's trash
I'D SAY IV. IT HAS THE BEST CAST AND IT'S FAIRLY "EASY" I HOWEVER, do not recommend going for the true ending because it's an absolute pain in the ass. Nocturne is my favorite, it has the best atmosphere and artistically speaking is goddamn beautiful, but it's HARD and requires a lot of patience
Shin Megami IV is the best starting point (the requirements for the neutral ending suck, though). Devil Survivor on DS is also good, but again, it is easy to get locked into an ending you hate. I still love both games, but it's good to be aware of how endings work (at least that is how I felt)
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I've also heard Strange Journey is fantastic and it'll probably appeal to you a lot but I haven't played it yet.