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The Four Kings (Dark Souls)
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Talk about a DPS test. The Four Kings are a required boss in DS1 and when the fight starts, you only have to deal with one of them, but after the first minute, a second one appears and then every minute after another appears. You can "kill" each of the kings, but if they still have health left before the time limit requirement, it's possible to fight five or six of them. They hit hard, have way better reach than they should, homing magic, a very powerful AoE ability for hip huggers, like to gang up on you, and have more health than some of the games optional challenge bosses. The only reason I was able to even beat these guys was because I lucked out and was able to summon a player with a very powerful sorcery build. Yet in every attempt to help another player beat them, I got trounced on pretty quickly. Did I mention that summoning help raises their health, effectively making this fight even harder since it raises the odds of always having four of them on the field at a time? There are certainly more challenging bosses in DS, but this one is required.
Redrum (Xenogears)
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Ah yes, the infamous Redrum. Xenogears vets will often tell you that he's the true final boss and everything after him is a cakewalk, and frankly that's not necessarily false. He's fast, loves to inflict confusion on party members to waste their turn, counters a lot, hits hard and has a special move that kills a party member and restores his own health with the character's drained health. That last move always works, can be used consecutively by the boss, and it doesn't matter if the boss hasn't been hit yet. Did I mention that two of the required party members for this fight have the highest HP in the game? He also has way more health than anything you've dealt with before. To make matters worse, he's the boss of the Kislev Sewers, yes a sewer dungeon, and one most players despise because it is incredibly easy to get lost in it. You're only safe bet to win, is to avoid using single Deathblows and charge up a 28 point Deathblow Chain Combo with all three party members and try to take him down in a single round. This may be an issue as well since Rico is a relatively new party member and will likely not have many strong deathblows by this point unless you grind in the dungeon. Even worse, he's the slowest party member as well, so getting him ready for this strategy may involve giving the boss extra rounds to out right murder a party member. Fun fact, halfway through the game, you can get into a battle where you have to fight two of them at once.
Kaiser Sigma (Mega Man X3)
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He is still the only Sigma I've never beater, but I may have to remedy that once Bloodborne and Persona 5 are finished with. He is certainly the hardest incarnation that doesn't have to rely on cheap one-hit-kills like some of his later incarnations. What makes this fight difficult is that Sigma's only weakness is his head, which is the smallest part of his body. He also takes very little damage when hit unless you have a certain upgrade that is itself a Guide Dang It and locks you into a slightly different ending. Part of the challenge is that this guy will turn the screen into a bullet hell nightmare with his various attacks, so trying to find an opening can be very challenging. The other issue, is that while the X-Buster upgrade seems ideal for this battle, it's probably one of the worst upgrades for the weapon in the series and simply makes timing the hits more difficult than necessary. I have simply not had the time or patience to deal with this boss properly, but he has given me far more grief than any other incarnation of the boss, including the awful X7 version.
Ouroboros (Shin Megami Tensei: Strange Journey)

Echoing Vermachtnis, meet Strange Journey's first (of many) Luck Based boss battle. The first form is manageable as the boss simply regenerates every round and uses Zio type spells than can easily be counters. Once that's part is done, the real battle begins. This boss has two really nasty attacks, Wave of Death, which is an absurdly powerful physical group hit that can do around 300+ of damage (max health in this game is 999 btw) and Disaster Cycle, a move that does moderate physical damage and has a high chance of inflicting one of the game various status effects on your whole party. Did someone get hit with Bomb status, well then they have to defend every round cause if they take a hit, they are instantly killed and the whole team takes damage equivalent to the amount of health the victim had at the time. Did you get hit with Stone? The character is counted as dead. Did I mention this was one of the SMT games that utilizes the whole "main character dies = Game over"? Even worse, there is no way to really protect your MC from any of these status effects either. So yeah, luck based mission.
The Dark One (Arc the Lad 2)
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smurf this guy. No seriously, this guy is the coup de grace of a blemish that seriously tarnishes what was ultimately an excellent SRPG title up until this point. This guy is the final boss, and he will make getting to the game's final ending a serious headache for you. He only has powerful elemental AoE moves, high evasions for a stationary boss, the highest HP of anything in the game at 9999hp (the previous boss had something like 4000HP to just put this in perspective), and ridiculous defense. To make matters worse, despite being a dude in a giant orb, he only takes damage from attacks directly in front of him and only one tile worth, meaning only one short range fight can hit him and everyone else will have to use magic (which he barely takes any damage from) or longer ranged weapons like guns and spears which often do pitiful damage. This fight pretty much took me an hour to win and the only saving grace I had was a simple A.I. exploit. He is programmed to always make Arc his primary target if he is on the playable team, so I simply had Arc move to the back of the map and try his best to survive the onslaught of enemy spells while the rest of the team moved forward and did as much damage as they could. Even with my best damage dealers, we were doing barely three digits worth of damage when they actually hit and I had to pretty much bring in two different healers to keep Arc alive long enough get the deed done, and I'm still pretty sure he eventually got killed because I blew through most of my MP for this fight. Part of me feels that I may have simply just missed some easy exploit that makes this fight trivial, but a quick look around the net shows that this may not likely be the case.
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