Hardest Boss Fights

There are a lot of games with incredibly difficult boss fights to consider even if I've only played Nintendo and some PSP games. While I never experienced playing the games that were deemed "Nintendo Hard" during the NES era, I have played some that were popularly addressed as such.
Like my Easiest Boss Fights list, this list will only include games that I've played on Nintendo and Sony handhelds. Also, the titles and boss fights listed here are all based on my opinion.

(The titles listed here are not in any specific order)

Title: Crisis Core Final Fantasy VII
Boss: Sephiroth
Reason: Sephiroth is the real big bad and ultimate in-game boss of Crisis Core. You think Genesis Avatar can do better, hah!, damn wrong. But it's not just about the boss fight, the scenario going towards the boss fight was part of it. You fight Sephiroth twice, both with frightening sudden death thanks to Heartless Angel if Phoenix Down and Curaga are out of reach. And as far as I remember, there're tons of cut-scenes at the beginning which you are forced to watch when you fall at long hair and long sword's superior SOLDIER 1st class skills.
Greatness Rating: 3/5

Title: Dissidia Final Fantasy
Boss: Chaos
the Edge of Madness arena (smallest home for the biggest enemy)
Reason: Surprise, surprise another Final Fantasy title. Maybe it's my mediocrity in 3D fighting games or just the space on the Edge of Madness stage and the damn size of the eldritch. The first time I fought Chaos was with Cloud at level 47, bad decision. So far the three best characters that I recommend for Chaos are Warrior of Light, Squall and Zidane. Warrior of Light's main attack starts of slow but it provides an all around protection during the move. Squall's Fated and Aerial Circle are quick and gets you closer to the enemy. Zidane is simply fast and small, 'nuff said.
One technique that I also found useful was when in Break mode don't go for a finisher, keep landing bravery attacks at critical and collect bravery points, the regen at Break mode is also helpful.
Greatness Rating: 2/5

Title: Super Mario 64 DS
Boss: Bowser
the Sky world is the two bottom pics
Reason: You fight Bowser three times at varying levels depending on which part of the adventure you are on. If I remember correctly, you need 5 stars on the first fight, 30 stars on the 2nd fight, and 70 in the last fight. The first two boss fights with Bowser in the creepy basement and the lava world were easy. The last boss fight was a leap of madness in difficulty. I don't know how many times I fell out of the course at Bowser in the Sky. It was such a long and tricky course to get to that you'd definitely trade in speed for patience. But the course was the least of my problems at that time.
When I finally got in the pipe that leads to Bowser, I suddenly found myself in one of the hardest boss fight during my elementary days. Bowser not only needed three hits to bite the dust, but he also turned the damn circular stage into damn star-shaped stage. It took me three months to finally get that damn Toadstool-crazy turtle-dinosaur to hit the last bomb.
Greatness Rating: 4/5

Title: Resident Evil Revelations
Boss: Rachel
Reason: Haha, Rachel isn't really that hard of a boss to fight in Revelations, what's more she's just the second boss in the whole damn game. But considering my Scaredy-cat ability which comes into play every now and forever you could or mostly could not imagine my face upon first encounter. Prior to Rachel's reappearance as an Ooze, a lot of Machine Gun and pistol ammo and bombs are lying around for you to collect if you use the Genesis smartly. By the time I got to Rachel, I had at least 300 bullets for the Machine Gun, 70 for the handgun, 30+ for the shotgun, 3 B.O.W. Decoys and 3 hand grenades, see the game itself was feeding all the ammo you can get. For the seasoned Resident Evil gamer, one hand grenade and the handgun might be enough but for me I had to run all the way back to the area with the Cafeteria to pick up Parker and join me in battling Rachel.

Rachel is a damn cheat. Every time she enters crisis mode she escapes at the vents above until you meet her finally at the cafeteria. It's definitely a long walk from there and with her stalking behind (or in front of you) with her sinister laughter and "I love you" chants, it's like having a date with paranoia. I didn't have any strategy fighting her. I just fire away, sometimes even forgetting the button input for reloading. I also used all four of my herbs to restore health. When she finally bite the dust (at least for now) I had only 3 bullets left for the handgun and 6 for the shotgun.
Sadly, that won't be the last of her.
Greatness Rating: 4/5

Title: Castlevania: Order of Ecclesia
Boss: Jiang-Shi
Jiang-Shi and Jiang-Shi Jr. know how to do da thrilla
Reason: Similar to Portrait of Ruin's Nest of Evil, Order of Ecclesia also has an extra difficult list of optional bosses in the Large Cavern area. But unlike Portrait of Ruin, Order of Ecclesia was already a difficult game on its own. The first bosses at the top of the stage are Weapon Masters and Double Hammers. I spent most of my healing items in my skirmish against them. I never dared to use the Nitesco + Melio Falcis combo drive because unlike Dracula, these guys were skedaddling all over the room. But they were nothing against the final boss of the Large Cavern - the Jiang-Shi.
The Jiang-Shi doesn't offer much physical offense against Shanoa, but its movement was tricky especially if those damn orbs starts flying all over the place, and he summons Jiang-Shi Jr. (the small version of himself).
One thing I still don't understand about this game is that, no matter how strong my equipment are, and how my high level is I still get heavy damage from a small bump.

It's also nice to note that never ever hit the Jiang-Shi again after the talisman has sealed him. Just go through the door, and keep on walking.
Greatness Rating: 2/5

Title: The Legend of Zelda: Ocarina of Time 3D
Boss: Bong-Bongo
Bongo-Bongo can really bongo, y'now? (I suck at rhyming)
Reason: Surprised that it's not Ganondorf? Don't worry, we'll get to that later. Bongo-Bongo is the boss of the eerie Shadow Temple. You fight him in his, yup you've guessed it, gigantic bongo drum. The Hover Boots are crucial in this boss fight, unless you want to bounce around trying to get a sure-spot hit but ultimately missing most of the time then by all means enter a sneak peek of Master Quest in Adventure Mode.
Bongo-Bongo's weak point is its eye which is visible through the Lens of Truth after hitting both hands when it comes charging at you. As with every Zelda bosses, precise timing and a fairy are crucial.
Greatness Rating: 3/5

Title: The Legend of Zelda: Ocarina of Time 3D
Boss: Ganondorf and Ganon
Reason: It took me a whole hour to finally get through these final boss fights. The first fight with Ganondorf atop Hyrule Castle was similar to the Phantom Ganon boss fight from the Forest Temple, to get a hit you must volley the magic projectile that Ganondorf launches at you until it hits him, then shoot a Light Arrow at him to stun him. Hookshot towards him then hack away. When he sustains enough damage, he will summon more dangerous projectiles before attacking with the one that can be volleyed. If ever Link sustains a great amount of damage, you can just climb down and break some pots to restore magic, hearts and items.

After Ganondorf is supposedly defeated, Princess Zelda will join you in escaping Ganon's Castle. It's just a few levels of dodging and defeating lesser enemies from there until you get out of the crumbling castle.
There will be some dialogue between  the two lovebirds and Navi, but wait there's more. Link will approach the castle ruins and to his surprise (but not ours) Ganondorf is alive, and powered up as Ganon (apparently the shorter the name, the stronger he is).
This second battle will be extra difficult because you don't have the Master Sword and there will definitely be a shortage of supplies. L-target Ganon's head as you move back avoiding his devastating attacks. Shoot a light arrow at his head and he will be stunned, once stunned quickly move beind him and L-target his tail and either shoot it with another light arrow or use the Goron's Knife (if you have one with you). Continue using this pattern until the next cut-scene where the flame barrier vanishes and Link can pick up the Master Sword.

If ever you fall short in health, magic and arrows, just hide behind the big crumbled walls inside the stage and wait until Ganon attacks it. If successful, the big walls will be destroyed but items will fall out from it. There's also a wall in the arena where red faeries will fly out (so bring a bottle with you).

When you've done enough damage, Zelda will join in the fray holding Ganon by force using her power. Deliver the final strike to Ganon's head and it's all over. Ganon is defeated and sealed away.
Greatness: 5/5

Title: Megaman Starforce Leo
Boss: Piano Jammers (I dunno what else to call them)
Reason: They aren't technically bosses but they did pose a great threat since they have the advantage in numbers making it sort of a boss rush. There will be no healing (only the battle chips will be restored per fight. All the enemies in each stage are all top tier. Some need specific types of battle chips for them to be defeated like the notorious blackhole which could only be damaged by blade type battle chips. I regret going into battle without any blade type battle chips. It was an endless fight against that damn black hole and I had no choice but to quit the game and restart the battle...it was heartbreaking. The reward for finishing the 10 battles and restoring peace in the piano is Zack's brotherband connection.
Greatness Rating: 1/5

Title: Super Mario 3D Land
Boss: Bowser (was there really anyone else?)
Reason: The last fight against Bowser wasn't technically a one-on-one dodge and attack fight like previous Super Mario titles. In 3D Land you, instead, escape from Bowser who's chasing Mario all the way to the top of the castle. At some point in the intense dodge and chase level, you'll have Bowser at the mercy of a press of a button. Mario, of course, with the right track of mind would step on the button that would make Bowser fall. But just when you think the chase is over, the clingy turtle dinosaur jumps right back up and we're up for another chase scene, this time a little harder though. While it's easy to dodge Bowser, the crumbling platforms are hard to predict. But there's no real worry here since, when you fall, you start over from the MIDPOINT of the whole final battle. I got stuck at one specific part during the second chase. It took me five tries (getting the Golden Tanooki suit in the process, which was useless in this case) before I finally got to the second platform button which gave Bowser is biggest dip in the game.
Greatness Rating: 5/5

Title: Mario and Luigi: Superstar Saga
Boss: Bowletta and Cackletta's soul
Bowletta
Reason: This boss fight is definitely one of the hardest that I had to endure and still came out victorious with only one try. Two reasons why I was really frustrated with this boss fight is that the R shoulder button of my very first Nintendo DS began malfunctioning mid-fight preventing me from using several moves which requires the button. What's more, I had to endure the match with the batteries on red.
Cackletta's soul
Bowletta is the resulting abomination when the soul of Cackletta possessed the body of Bowser. The first round battle with him/her/it whatever was already grueling with 500 HP to drain. When all was said and done in the first round, down goes the brothers inside Bowser and fights Cackletta's soul. Sounds simple? NO. The bros. start of at 1 HP. Of course, healing is first priority, but then again Cackletta's hard to predict attack is a real pain. She also has several super moves and that damn Fawful joining in the fray every now and then was really annoying. While Cackletta has a lower HP than Bowletta, she does have a lot of body parts to target.
I only experienced that grueling part once because I only borrowed the game cartridge from a friend. Needless to say, it's one of the most memorable boss fights during my elementary days.
Greatness Rating: 5/5

Title: Castlevania: Portrait of Ruin
Boss: Dracula and Death, True Dracula
Reason: Dracula is naturally the last boss in most Castlevania games. In Portrait of Ruin, it seemed to be the return of that formula after the Sorrow titles finished their run in the GBA and DS with Aria and Dawn, respectively. But Konami had another thing in mind for the last battle, it's two on two. Dracula's best friend, secretary, confidant, butler or whatever it is you want to call Death aids Dracula in the final battle. The first round was a tornado tag but it's best to keep only one of your characters on the screen to save MP. Dracula will attack the same way he has done for the past 10 centuries, teleporting then summoning fireballs and dark orbs rushing towards you. These are generally easy to dodge but Death will constantly slash through the screen either vertically or horizontally depending on your position.
The two also have three super moves signaled by Death positioning himself directly above Dracula with his arms spread out. These three super moves are the infamous Demonic Megiddo, an up-sized version of Dark Inferno and a rush of multi-hard hitting bats.

Round 2 starts when either Dracula are Death sustained enough damage equal to their first HP in round 1 (4444 for Death and 6666 for Dracula), after that Death will offer his power to Dracula, and Dracula will use soul steal to absorb Death. Round 2 will only feature a powered-up Dracula at 6666 HP. His attacks are more physical and brutal. I only consider two of his moves as super-moves. One will be his "Wing Crush" where he will go to the background and his wings will cover the screen. If his wings end up closing the whole screen, it will do a massive damage resulting in instant death. The other super move is where he throws scythes which flies towards a third of the the screen before flying upwards. I just continued hitting him with the Vampire Killer and Dual Crush of Greatest Five till his down for the count.
Greatness Rating: 5/5

*I'll still update this list whenever I encounter (or remember) a difficult boss fight

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