10. Astarte (PoR)-I'll admit, she may not be the coolest looking or the most original idea, but heck she is the only boss I can think of that can kill a level 80 in boss rush due to the fact that if Jonathan gets hit by her "temptation" spell, he goes on a murderous rampage and wastes Charlotte. Barbaric.
9. Behemoth(PoR)-This half rotted blue lion creature was scary when it chased you down in the beginning, but was even cooler during the boss battle. Those rotting worms were a good touch, too.
8. Tie-The Creature & The Werewolf (both being the ones from PoR)-They are both cool so they both stay. The Creature is the powerful frankenstein rip-off that will electrocute you to death, while the Werewolf is the big furry thing that throws lamp posts at you. I'll stay on 12th and 14th streets, mind you. (If you played the dungeon, you'd understand)
7. The Doppelganger(PoR and SotN)-This guy is rad. He is you, except stronger and more murderous. Have fun with the annoying ones in SotN, but in PoR, he dupes your armor too, so crappy armor is the key to a super simplistic fight.
6. Medusa(like freaking everything)-This chick is angry. If her heads aren't going to make you kill yourself (I almost did), then she will gladly. Though the SotN one was so easy due to the mirror armor, the one in PoR doesn't pull punches. That's why god invented the Greatest Five.
5. Fake Grant, Trevor, Sypha(PoR, SotN)-This ain't easy. You have the whip slinging, Richter-rip-off Trevor, Grant, the eerie spiderman assasin, and Sypha, the chick whos magic is best to be avoided. Cool boss. Ironically, Fake Trevor is in a game with Richter as a boss twice (SotN and Whip's Memory in PoR), so it is like you have to fight him twice.
4. Death(same as Medusa)-Nothing says old-school like the Grim Reaper. He is Dracula's right hand for a reason, being annoyingly hard (at lest for me) in PoR and Aria of Sorrow. Heck, he even combined with Dracula to make a huge demon. That's bad @$$.
3. Beezlebub(SotN)-Harkening to number one, this dude is baaaddd. It is a huge corpse suspended by chains that you have to slice up. Heck, he doesn't even hit you. So how can he be hard? Two words: giant flies.
2. Dracula(everything in the universe)-Why do Belmonts hate him? He is a good role model. He teaches you to be persistant. Veeerrryyy persistant.
1. Legion(AoS, HoD, PoR, SotN [under a different name])-I swear to the video game gods this is one of my favorite boss battles ever. This huge being is composed of hundreds of corpses. If that isn't bad enough, he constantly drops them on you, and even when you strip him down with your weapon, the inside is a huge tentacle monster. Lord. Oh, and the one from AoS with a face--*shudders