Just buy a $10-20 controller for your PC. It's always a good idea to have one just in case you find something worthwhile. I can't stress enough how much you need to play Symphony of the Night though. If this were Zelda, this would be the equivalent of never having played Ocarina of Time. Or if you don't have anything against Sony personally, spend the cash on a PSOne and a copy of Symphony of the Night. You can probably grab a PSOne for $20 and Symphony for $40.

The original NES Castlevania is still my favorite, although I love virtually the entire series (with the exceptions of Castlevania Legends and the N64 games, which should be the last ones you try out). Of course the original NES game is cheap and easy to get a hold of, plus it's one of the best games ever with superb music and very challenging gameplay. If you aren't one to deal with challenge, try Symphony of the Night or Aria/Dawn of Sorrow, all very good stuff. Of the old GameBoy games, Belmont's Revenge is by far the best and one of the best portable games ever.

You've also left off Dracula X for PC Engine (TurboDuo), but that is very expensive (although a great game). Another related (and good) game is Kid Dracula for GameBoy.

Is starting with the NES ones a good idea, I dont mind a challenge in games as I have alot of games that tend to lean to the easy side, so Im looking for something a little harder, also out of the 3, whats the order best to worst?

My take:

*Castlevania III (NES) is the best, tradtional, game in the series (i.e. not a riff on Metroid) and is also quite difficult.

*Castelvania: Legacy of Darkness (N64) is the most underrated by a large margin (mainly by people that have never played it).

*SOTN (PS1/XBLA/PSN) or Portrait of Ruin (DS) are the best "Castleroids" but both are very, very easy games.

*Super Castlevania IV (SNES) is probably the most overrated of the lot.

Hope that helps.

Seriously, if you want good challenge, play all the old Castlevanias (NES, SNES, GB). They don't have that RPG element where you level up from the PS1, GBA and DS... which obviously makes the game a lot easier. Stay away from the 3D ones, please!

Like everyone said, the series' best game is Symphony of the Night for the PS1, but you should really try Harmony Of Dissonance on the GBA. I really enjoyed it, and the main castle theme is just catchy! The Sega Genesis one is also very good.

For your question, I'd say:
Castlevania > Castlevania III > Castlevania II.

Have fun!

I'd suggest you start with the SNES games first(where the pre SOTN style was perfected)
and the maybe play the GBA games before moving on to the main course that is SOTN. You really have to savour it like Super Metroid or Ocarina Of Time.

Castlevania is one of my fav series! The earlier games are well hard & not as fun imo. I would suggest Castlevania Dawn of Sorrow. You can level up so if ur good u won't have to, but if ur having a hard time just level up. U can also buy potions & mana if ur having a hard time as well (kinda takes the fun away but if ur having a hard time it's there).

But main reason, there is so much customization, u can take souls of all the bad guys (and this gives u a move/ability), which means 100+ moves!

Am I the only one who thought Castlevania II was really cool! Okay, there's some things you have to do that are next to impossible to figure out on your own but I really like buying crystal and weapons, collecting hearts.

That being said, I would still recommend Symphony of the Night and Castlevania IV over Castlevania II.

Truck, you're not the only one. Castlevania II has a lot of things going for it. There are a few flaws, such as terrible translation leading to mangled/incomprehensible clues, and in some cases random puzzles with no clues at all, but still a very fun game to play through...but it is one of the few games where I recommend not being afraid to use a FAQ when necessary.

I'd still say start with the original, then Castlevania III on NES. Castlevania III is a longer game with multiple paths and multiple endings, three different partner characters, new elements, etc. Plus it has the best soundtrack of any game for any system ever, period. And it's just as challenging, if not more so, than the original (a game many people describe as one of the harder games they've ever played).

This has no bearing on the order in which to play the games, but I highly, HIGHLY recommend Aria of Sorrow. It's actually a toss-up for me between that game and SOTN for my favorite of the series. It's fairly short, but man, is it sweet.