If you can appreciate very old gameplay mechanics, like very rigged jumping in a platformer, start with Castlevania and Castlevania II: Simon's Quest. Skip Castlevania III. Move onto Super Castlevania IV and Dracula X as both have more evolved control mechanics.
Next find a way to play Symphony of the Night. I'm not kidding. It's the definitive Castlevania, and if you have any interest in the Pre-Prime Metroid series, you'll definitely adore it. Even if it's a matter of you playing a ROM over an emulator on your comp, just get this game somehow. I can't recommend it highly enough.
Lastly, move onto the GBA and then DS games. Skip all N64 and PS2 Castlevania's.








