I loved the Gen 2 games for a lot of reasons, but my big issue with them was always the level scaling. It never made any sense to me that you could play through Johto and Kanto both and even after beating every trainer in the game your team would still be ten levels lower than they were at the end of the Gen I games. I don't know if it was GF's intent, but I always thought of Whitney as a way to help you compensate for that. There's no way to have your whole team of 3 or 4 Pokemon at that Miltank's level or higher by the time you get to her if you just do trainer battles, so you end up grinding in the tall grass until you're strong enough to be sure of a victory, and that sets the stage for doing more of that later on in the game.
As far as tougher bosses, Nihlathak in Diablo 2 was a pain in the ass on almost every difficulty, especially for first-timers who didn't know what they were getting into.
Johto was intentionally designed with a "pick your own path" system after, I think, Badge 3. So the level curve was made so that any of the three available paths would be at your level. Which meant that like half the region wasn't available for being part of the level curve because of redundancy.
Kanto was similar in that you could technically do Badges 4-6 in roughly any order and the level curve was only slightly prohibitive to doing so. But it wasn't nearly to the level Johto was. And it didn't have a fucking final boss in the 80s with a super strong team, so you could just finish Red/Blue with a team leveled pretty normally into the high 50s and be happy.
Its how you can tell that the legions of people who claim HeartGold/SoulSilver are the best/favorite games play them exclusively on emulator or with traded from elsewhere Pokemon. Because playing them actually like they were designed is literal misery no matter what other good they bring.
And I played the original on Gameboy, where it had the excuse of being super primitive as to why its filled with bad decisions and design, instead of a full price remake that spent its time adding half a dozen gimmicks instead of fixing one of the biggest issues with the game.
Pre-nerf Onyxia in vanilla WoW. Despite playing through dozens of solid games in my teens, WoW raids taught me what bosses even were. I could never have imagined wiping to overtuned or bugged bosses a bajillion times with friends would be so fun (before I realized how much time it cost me...).
Atma Weapon in Final Fantasy 6 (3). I have no idea why. I can't explain in detail the way you did. It just hit me out of nowhere. I was beating the bosses just fine until that guy on the floating continent completely halted my progress. Eventually I got help from a friend. We played the game in 2P mode where you can both fight battles together, and we stayed up all night eventually defeating it. Epic moments in JRPG gaming.
Haven't played Gold or Silver but when I encountered such challenging opponents, my typical strategy as a kid was to head back and level up until I thought that I was ready. This was the presumable purpose of this particular opponent to begin with.
Often times, after you'd dealt with the boss, you'd find out that you're much more powerful than anything that came after that for a while. :') Now-a-days I just consider that broken game design.
Matador from Shin Megami Tensei III: Nocturne. He singlehandedly taught an entire generation of gamers to never ignore buffs and debuffs. Not only in that game, but in every game in the SMT franchise going forward.
Crimson from Digimon World 2. He brings two very strong Ultimates who both have obscene status effects. The first literally blocks your two strongest attacks from being used, while the other heavily debuffs Vaccine type Digimon (the most common team people usually join). And one of them has obscene defense to stop you from nuking him before they get rolling. And he comes after another decent boss prior and has a fucking nother boss after him.
The entirety of Data Domain literally 2-3 missions later is even worse. Where you have a gauntlet of like 7 bosses in a row, all of which are confusion themed. Its usually recommended to just do 2 or so, leave and then come back. Because they stay defeated, and the hour+ time loss is easier than the huge item loss you'll use trying to recover after each one. Made even worse by the fact that most of their Mons are fucking terrible and would be a joke without the Confusion hell.
And its a dungeon crawler, so its not like you are ever walking up to them topped off on health/mana. You are getting fucking dragged by Digimon that are only a step below them attacking you constantly while you desperately try to find the Floor Portal to go down. While also staving off your Tank running out of health/mana itself (an instant return to base with a huge item loss cost), while also dodging Bug Traps because if you get unlucky and its a Return Bug (which will send 0-3 Digimon back home and out of your team) you basically have to just give up. All of these things can be fixed with items, but you have an item limit so any Healing Disc means one less Bug Zapper or Drill Missile you might need to progress.
Honestly, every boss in the game could qualify after the first 3rd.
Two (sets) come to mind for me immediately, though one is semi-optional (you have to fight, you don't have to necessarily win, but you can't just lose either).
Al-Van in Super Robot Wars J. Much like the later entry on this list... the secret is he's a boss from later in the game. At stage 20 you fight him. Al-Van's personal stats as a pilot are on par with what enemies of that point in the game should have. His robot's stats on the other hand, are roughly what they are later in the game when you fight him to the death, at stage 38. I think there may be a couple upgrades' difference for the robot but that amounts to a few hundred more points of armor and damage to weapons as well as a few points of dodge and accuracy that's more overshadowed by the level gap for the pilot, honestly. Al-Van hits like a truck, has a shield (chance to reduce damage to 40%, always used if defending and a chance to use when counterattacking/being counterattacked based on how much higher his Skill stat is than the other unit [as a boss he'll have higher skill unless you deliberately pumped that stat]), a strong attack that can one-shot your dodgier guys if they eat a crit (skill influences crit rates), and once the fight's been going a while and it hits 120 morale (trivially easy) the real fun starts. Two things activate at that point, a barrier that reduces all final damage by 1200 is added in, which is calculated after the shield, and a 50~% (skill gap influences exact chances) to just stop time and dodge an attack, regardless of what the hit rate says. The only way to circumvent the dodge is to use the Spirit command, Strike which forces a 100% hit rate and overrides everything else (including when the enemy is scripted to use Flash which is a 100% dodge). Al-Van also regenerates 30% of his energy every turn so a strategy of bleeding him dry doesn't hold up. It's a particularly rough "get serious" moment because when does he show up? As a third wave of enemy reinforcements. Most players not expecting this will have spent a lot of their SP on the previous enemies and then be caught unprepared for the ambush.
Super Robot Wars OG2 had a trio of semi-optional bosses on stage 15. They are endgame bosses (you fight them for real on stage 38 out of 43) with the same stats for their units as the endgame, but lower pilot stats (they're still overleveled for the stage) so you have an actual chance to hit them. Emphasis on chance. Your have four units for the stage and they're new with no prior chance to upgrade (or neglect, tbf) them that it's purely up to your stubbornness and awareness as a player if you want to fight them and if that fight is winnable. The mission objective is to escape, but you can fight and beat them. There's a big object that gives hp and energy regen, as well as defense and dodge bonuses. But you frankly have no chance of winning if the enemies position on that terrain themselves (Literally no chance, the hp regen will be greater than your damage output even if all your attacks hit). You need to control the AI and pace yourself for a marathon with knowledge that you WILL not be able to just plop units down and keep them there, since you have no resupply unit and have to move units into your battle ship to reload ammo so they'll be able to finish the fight. Fortunately the enemies and your party do talk before the fight starts and the bosses each call dibs on one particular unit, so you know who will be attacked by who and in theory won't have a string of just getting hammered more than you're able to deal with. It's about as pure a test of player knowledge as you can get in a game like that by making it default units only with no chance to dump all your resources into them before the fight or be screwed by just not using the unit and suddenly having them be a mandatory deploy. (Though if you kill the wrong enemy first he'll retreat and the other two will go with him, denying you the rewards for defeating them which are some really, really good items)
The boss in a tower in Ys 8 in which the perspective gets locked in a sort of isometric view and has some bullet hell style attacks. Very different from every other boss.
The little girl boss in Trails In The Sky who opened with a special attack on all which has a chance of instant death. I think I lost 3 out of 4 to that. I struggled to recover then quit and loaded an older save to equip an accessory to prevent instant death.
In Tales of Maj'Eyal, there's a "hidden tomb" that your character automatically finds early-mid-game. In a turn-based grid-movement RPG, it's filled TO THE BRIM with super high damage long range sniper casters. Even on normal, you're dying unless you git gud. And it's a roguelike, enjoy the two-three hour reroll to get back to that point. That ritual site is full of winding corridors and sharp corners, and the enemies will usually never hurt their own team, usually, so the entire engagement is all about learning your own positionals, and engaging tactically.
Even knowing this, many experienced players stand by skipping the dungeon entirely, because the nature of its time-limited appearance and appearing so early, before many classes have good movement or long-range-fighting options. It is, however, core to MANY unlocks in the roguelike system, so everyone will need to learn how to not stand in the crossfire of 50 rot mages eventually.
The Eye of Valmar from Grandia 2 is a standout to me.
Grandia 2 was one of the early RPGs to show you enemies on the world map and let you avoid them. In games like that it was commonplace to skip many of the "trash" battles and stay at a level that was just high enough to clear bosses with some challenge, but without fighting everything or grinding. This was great! ...Until you met the eye.
So picture a huge boss that uses wide AOE status effects and hits fairly hard by itself but has a shitton of HP. And its fast, getting 1.5 to 2 turns to your one if you're underleveled. It can put your party members to sleep with a hugely damaging special move, and once slept (assuming they survive the damage) they lose 3-4 turns unless you had happened to stock up on heretofore useless Smelling Salt items. Next the boss came with 3 minions. Little flying eyeball dudes, whose attacks were individually weak but fast, so they were constantly smacking your party members around for chip damage and forcing them down in the turn order because attacks reduce initiative.
All that was bad enough, but if all three minions were alive they could execute a team attack called Delta, which would VERY easily one hit kill a party member from full HP. And if someone died? Well revive items were rare and cost 5000G IIRC, and since you werent grinding you never had the money to buy more than a couple and you never needed them anyway so you probly don't have more than a handful.
And did I mention this boss had a nice, pretty save point right before its fight room in a dungeon that you couldn't leave once you entered? Yeah, this son of a bitch was a point of no return boss, so if you think you're gonna just go out and grind some G to buy the items you need then think again. If my memory serves me the Eye of Valmar was literally the TVTropes posterboy for both "Wakeup Call Boss" and "That One Boss" many years ago. I was one of the generation who got to experience it firsthand.
Honestly the fact it kept milking itself was what was left to linger in my mind. It was a very strange thing to imagine and absolutely obnoxious to deal with. It was one of the earliest forms of mechanical trolling I think I was exposed to.
It's admittedly a normie take, but I don't play a ton of games with that sort of standout boss. So I just thought, which Dark Souls bosses gave me trouble?
And, it's the classics, with the exception of Ornstein and Smough, who I found easy. But, dang, Knight Artorias made me work for it, as did Kalameet there at the end.
I loved the Gen 2 games for a lot of reasons, but my big issue with them was always the level scaling. It never made any sense to me that you could play through Johto and Kanto both and even after beating every trainer in the game your team would still be ten levels lower than they were at the end of the Gen I games. I don't know if it was GF's intent, but I always thought of Whitney as a way to help you compensate for that. There's no way to have your whole team of 3 or 4 Pokemon at that Miltank's level or higher by the time you get to her if you just do trainer battles, so you end up grinding in the tall grass until you're strong enough to be sure of a victory, and that sets the stage for doing more of that later on in the game.
As far as tougher bosses, Nihlathak in Diablo 2 was a pain in the ass on almost every difficulty, especially for first-timers who didn't know what they were getting into.
Johto was intentionally designed with a "pick your own path" system after, I think, Badge 3. So the level curve was made so that any of the three available paths would be at your level. Which meant that like half the region wasn't available for being part of the level curve because of redundancy.
Kanto was similar in that you could technically do Badges 4-6 in roughly any order and the level curve was only slightly prohibitive to doing so. But it wasn't nearly to the level Johto was. And it didn't have a fucking final boss in the 80s with a super strong team, so you could just finish Red/Blue with a team leveled pretty normally into the high 50s and be happy.
Its how you can tell that the legions of people who claim HeartGold/SoulSilver are the best/favorite games play them exclusively on emulator or with traded from elsewhere Pokemon. Because playing them actually like they were designed is literal misery no matter what other good they bring.
I played them originally on DS. I loved them. The Pokewalker was neat. Sit and spin.
And I played the original on Gameboy, where it had the excuse of being super primitive as to why its filled with bad decisions and design, instead of a full price remake that spent its time adding half a dozen gimmicks instead of fixing one of the biggest issues with the game.
The frustration when the mount finally drops and it just somehow happens to go to the guild leader's wife despite the roll.
Pre-nerf Onyxia in vanilla WoW. Despite playing through dozens of solid games in my teens, WoW raids taught me what bosses even were. I could never have imagined wiping to overtuned or bugged bosses a bajillion times with friends would be so fun (before I realized how much time it cost me...).
Atma Weapon in Final Fantasy 6 (3). I have no idea why. I can't explain in detail the way you did. It just hit me out of nowhere. I was beating the bosses just fine until that guy on the floating continent completely halted my progress. Eventually I got help from a friend. We played the game in 2P mode where you can both fight battles together, and we stayed up all night eventually defeating it. Epic moments in JRPG gaming.
Haven't played Gold or Silver but when I encountered such challenging opponents, my typical strategy as a kid was to head back and level up until I thought that I was ready. This was the presumable purpose of this particular opponent to begin with.
Often times, after you'd dealt with the boss, you'd find out that you're much more powerful than anything that came after that for a while. :') Now-a-days I just consider that broken game design.
Matador from Shin Megami Tensei III: Nocturne. He singlehandedly taught an entire generation of gamers to never ignore buffs and debuffs. Not only in that game, but in every game in the SMT franchise going forward.
Crimson from Digimon World 2. He brings two very strong Ultimates who both have obscene status effects. The first literally blocks your two strongest attacks from being used, while the other heavily debuffs Vaccine type Digimon (the most common team people usually join). And one of them has obscene defense to stop you from nuking him before they get rolling. And he comes after another decent boss prior and has a fucking nother boss after him.
The entirety of Data Domain literally 2-3 missions later is even worse. Where you have a gauntlet of like 7 bosses in a row, all of which are confusion themed. Its usually recommended to just do 2 or so, leave and then come back. Because they stay defeated, and the hour+ time loss is easier than the huge item loss you'll use trying to recover after each one. Made even worse by the fact that most of their Mons are fucking terrible and would be a joke without the Confusion hell.
And its a dungeon crawler, so its not like you are ever walking up to them topped off on health/mana. You are getting fucking dragged by Digimon that are only a step below them attacking you constantly while you desperately try to find the Floor Portal to go down. While also staving off your Tank running out of health/mana itself (an instant return to base with a huge item loss cost), while also dodging Bug Traps because if you get unlucky and its a Return Bug (which will send 0-3 Digimon back home and out of your team) you basically have to just give up. All of these things can be fixed with items, but you have an item limit so any Healing Disc means one less Bug Zapper or Drill Missile you might need to progress.
Honestly, every boss in the game could qualify after the first 3rd.
Two (sets) come to mind for me immediately, though one is semi-optional (you have to fight, you don't have to necessarily win, but you can't just lose either). Al-Van in Super Robot Wars J. Much like the later entry on this list... the secret is he's a boss from later in the game. At stage 20 you fight him. Al-Van's personal stats as a pilot are on par with what enemies of that point in the game should have. His robot's stats on the other hand, are roughly what they are later in the game when you fight him to the death, at stage 38. I think there may be a couple upgrades' difference for the robot but that amounts to a few hundred more points of armor and damage to weapons as well as a few points of dodge and accuracy that's more overshadowed by the level gap for the pilot, honestly. Al-Van hits like a truck, has a shield (chance to reduce damage to 40%, always used if defending and a chance to use when counterattacking/being counterattacked based on how much higher his Skill stat is than the other unit [as a boss he'll have higher skill unless you deliberately pumped that stat]), a strong attack that can one-shot your dodgier guys if they eat a crit (skill influences crit rates), and once the fight's been going a while and it hits 120 morale (trivially easy) the real fun starts. Two things activate at that point, a barrier that reduces all final damage by 1200 is added in, which is calculated after the shield, and a 50~% (skill gap influences exact chances) to just stop time and dodge an attack, regardless of what the hit rate says. The only way to circumvent the dodge is to use the Spirit command, Strike which forces a 100% hit rate and overrides everything else (including when the enemy is scripted to use Flash which is a 100% dodge). Al-Van also regenerates 30% of his energy every turn so a strategy of bleeding him dry doesn't hold up. It's a particularly rough "get serious" moment because when does he show up? As a third wave of enemy reinforcements. Most players not expecting this will have spent a lot of their SP on the previous enemies and then be caught unprepared for the ambush.
Super Robot Wars OG2 had a trio of semi-optional bosses on stage 15. They are endgame bosses (you fight them for real on stage 38 out of 43) with the same stats for their units as the endgame, but lower pilot stats (they're still overleveled for the stage) so you have an actual chance to hit them. Emphasis on chance. Your have four units for the stage and they're new with no prior chance to upgrade (or neglect, tbf) them that it's purely up to your stubbornness and awareness as a player if you want to fight them and if that fight is winnable. The mission objective is to escape, but you can fight and beat them. There's a big object that gives hp and energy regen, as well as defense and dodge bonuses. But you frankly have no chance of winning if the enemies position on that terrain themselves (Literally no chance, the hp regen will be greater than your damage output even if all your attacks hit). You need to control the AI and pace yourself for a marathon with knowledge that you WILL not be able to just plop units down and keep them there, since you have no resupply unit and have to move units into your battle ship to reload ammo so they'll be able to finish the fight. Fortunately the enemies and your party do talk before the fight starts and the bosses each call dibs on one particular unit, so you know who will be attacked by who and in theory won't have a string of just getting hammered more than you're able to deal with. It's about as pure a test of player knowledge as you can get in a game like that by making it default units only with no chance to dump all your resources into them before the fight or be screwed by just not using the unit and suddenly having them be a mandatory deploy. (Though if you kill the wrong enemy first he'll retreat and the other two will go with him, denying you the rewards for defeating them which are some really, really good items)
The boss in a tower in Ys 8 in which the perspective gets locked in a sort of isometric view and has some bullet hell style attacks. Very different from every other boss.
The little girl boss in Trails In The Sky who opened with a special attack on all which has a chance of instant death. I think I lost 3 out of 4 to that. I struggled to recover then quit and loaded an older save to equip an accessory to prevent instant death.
So a throwback to Ys 1? Interesting. I haven't touched the series since NISA got their hands on it.
Only very vaguely is it like Ys 1 and I certainly wasn't thinking that at the time.
In Tales of Maj'Eyal, there's a "hidden tomb" that your character automatically finds early-mid-game. In a turn-based grid-movement RPG, it's filled TO THE BRIM with super high damage long range sniper casters. Even on normal, you're dying unless you git gud. And it's a roguelike, enjoy the two-three hour reroll to get back to that point. That ritual site is full of winding corridors and sharp corners, and the enemies will usually never hurt their own team, usually, so the entire engagement is all about learning your own positionals, and engaging tactically.
Even knowing this, many experienced players stand by skipping the dungeon entirely, because the nature of its time-limited appearance and appearing so early, before many classes have good movement or long-range-fighting options. It is, however, core to MANY unlocks in the roguelike system, so everyone will need to learn how to not stand in the crossfire of 50 rot mages eventually.
The Eye of Valmar from Grandia 2 is a standout to me.
Grandia 2 was one of the early RPGs to show you enemies on the world map and let you avoid them. In games like that it was commonplace to skip many of the "trash" battles and stay at a level that was just high enough to clear bosses with some challenge, but without fighting everything or grinding. This was great! ...Until you met the eye.
So picture a huge boss that uses wide AOE status effects and hits fairly hard by itself but has a shitton of HP. And its fast, getting 1.5 to 2 turns to your one if you're underleveled. It can put your party members to sleep with a hugely damaging special move, and once slept (assuming they survive the damage) they lose 3-4 turns unless you had happened to stock up on heretofore useless Smelling Salt items. Next the boss came with 3 minions. Little flying eyeball dudes, whose attacks were individually weak but fast, so they were constantly smacking your party members around for chip damage and forcing them down in the turn order because attacks reduce initiative.
All that was bad enough, but if all three minions were alive they could execute a team attack called Delta, which would VERY easily one hit kill a party member from full HP. And if someone died? Well revive items were rare and cost 5000G IIRC, and since you werent grinding you never had the money to buy more than a couple and you never needed them anyway so you probly don't have more than a handful.
And did I mention this boss had a nice, pretty save point right before its fight room in a dungeon that you couldn't leave once you entered? Yeah, this son of a bitch was a point of no return boss, so if you think you're gonna just go out and grind some G to buy the items you need then think again. If my memory serves me the Eye of Valmar was literally the TVTropes posterboy for both "Wakeup Call Boss" and "That One Boss" many years ago. I was one of the generation who got to experience it firsthand.
Honestly the fact it kept milking itself was what was left to linger in my mind. It was a very strange thing to imagine and absolutely obnoxious to deal with. It was one of the earliest forms of mechanical trolling I think I was exposed to.
The office tower maze in red/blue
It's admittedly a normie take, but I don't play a ton of games with that sort of standout boss. So I just thought, which Dark Souls bosses gave me trouble?
And, it's the classics, with the exception of Ornstein and Smough, who I found easy. But, dang, Knight Artorias made me work for it, as did Kalameet there at the end.
kys
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