History GoddamnedBoss / Pokemon

* Lugia in [=HeartGold=] and Ho-Oh in ''[=SoulSilver=]'' learn the move Safeguard at level 65 (which blocks status effects for five turns), and are encountered at level 70. Because of this, you can count on them to spam it throughout the fight, especially later on once they've run out of PP for their attacking moves (and all their attacking moves have really low PP). This makes putting them to sleep or paralyzing them far more difficult, driving down their already low catch rates.

* Juan from ''Emerald'' isn't too bad until his ace Kingdra. He's only weak to Dragon, but unless you have a Kingdra of your own (which can only be acquired from trade) all possible Dragons are vulnerable to a 4x effective Ice Beam. However, this Kingdra in particular comes with the infuriating combo of Double Team and Rest. He'll start setting up Double Team and if you get hits in, heal himself up with Rest, which will also remove any status afflicted on it. If you're particularly unlucky, you'll be dealing with all your attacks unable to land on a sleeping Pokemon and he'll wake up to attack, raise evasion, and heal. This can rectified with any moves that bypass accuracy checks like Aerial Ace, though.

* In ''Black 2'' and ''White 2'' in the Pokemon World Tournament: Winona, specifically her Altaria. While most of the gym leaders will either give you an even battle [[ThatOneBoss or just murder you outright]], Winona's Altaria seems designed specifically to cause hair pulling. Of its four moves, only ''one'' is damaging (Dream Eater) and it only works when your mon is sleeping. The others put your Pokemon to sleep, preventing them from attacking and making them vulnerable to Dream Eater (Sing), recover health (Roost, and also Dream Eater if it works), or boost Altaria's defense (Cotton Guard). So a typical battle has her put your mon to sleep with Sing, heal any damage you may have done with Roost, and then bulk up with Cotton Guard and proceed to use Dream Eater until your Pokemon wakes up, in which case you had better hope you get a Super Effective Critical Hit before you get put to sleep again. It's not quite ThatOneBoss, because unless your mon is extremely vulnerable to Dream Eater, Altaria can't cause much damage, but its moveset seems basically designed to drag the match out as long as possible and make you waste all your good moves trying to KO Altaria before it can heal itself.

* In ''VideoGame/PokemonSwordAndShield'', the only thing keeping the Gigantamax forms of Pikachu and Eevee from being ThatOneBoss is that, not being fully evolved, their defenses are paper-thin. However, they both tend to run essentially the same strategy of trying to stop the player's side from getting to attack at all. Pikachu's signature move, G-Max Volt Crash, paralyzes the entire party, including Ground-types that the attack itself can't even hit, and then spams Double Team to try and make sure any Pokemon that do get to move will miss anyway. Eevee manages to be just as annoying; its signature move, G-Max Cuddle, inflicts infatuation on any opposing Pokemon of the opposite gender from Eevee itself, forcing them to stand by and do nothing 50% of the time, and as salt in the wound, Eevee also comes knowing Sand-Attack to lower the player's accuracy even further and ''Endure'', a move that guarantees itself a LastChanceHitPoint for a full turn, dragging the fight out even more.

* Agatha is infamously annoying for any player doing a SoloCharacterRun, to the point that she's been nicknamed "the Agatha Lottery." Her team consists of multiple versions of the Gastly line, plus Venomoth and Arbok, and she heavily emphasizes status effects, as well as having a randomized chance to switch every turn. Since Gengar has very high Speed, it's likely to get off a Confuse Ray or Hypnosis on the first turn, dragging out the fight even further, and while it is weak to Psychic and Ground-type moves, it's also totally immune to Normal-type moves, which many Pokémon rely on for offense. This leads to cases where [[LuckBasedMission sometimes Agatha does nothing of importance and dies in five attacks, and sometimes she stalls you out and chips you to death]].

* There's also Pre Gym Leader Justy from ''VideoGame/PokemonColosseum'', who uses a combination of Double Team, Sand Veil and Dig to keep you from hitting him. This leads to a tedious battle of spamming Faint Attack with Umbreon (if you taught it that; the Bite it comes with is usually more preferable) or Swift with Espeon (which no one does since it comes with Return).

* In ''Black 2'' and ''White 2'' in the Pokemon World Tournament: Winona, specifically her Altaria. While most of the gym leaders will either give you an even battle [[ThatOneBoss or just murder you outright]], Winona's Altaria seems designed specifically to cause hair pulling. Of it's four moves, only ''one'' is damaging (Dream Eater) and it only works when your mon is sleeping. The others put your Pokemon to sleep, preventing them from attacking and making them vulnerable to Dream Eater (Sing), recover health (Roost, and also Dream Eater if it works), or boost Altaria's defense (Cotton Guard). So a typical battle has her put your mon to sleep with Sing, heal any damage you may have done with Roost, and then bulk up with Cotton Guard and proceed to use Dream Eater until your Pokemon wakes up, in which case you had better hope you get a Super Effective Critical Hit before you get put to sleep again. It's not quite ThatOneBoss, because unless your mon is extremely vulnerable to Dream Eater, Altaria can't cause much damage, but its moveset seems basically designed to drag the match out as long as possible and make you waste all your good moves trying to KO Altaria before it can heal itself.

* Cotton Down Eldegoss is ''extremely'' tedious to fight in a Max Raid. While Eldegoss isn't strong enough to be that dangerous offensively, or quite durable enough to stall out the 10-turn limit, Eldegoss's Cotton Down ability makes it a total pest on a meta level. Cotton Down is an ability that activates every time Eldegoss is hit by a damaging move, which gives off cotton spores and lowers the Speed of everything except itself. This by itself is only mildly annoying, but the specifics of Cotton Down being on a Max Raid boss is what makes it truly aggravating: the ability activates ''every'' time Eldegoss gets hit, it gives a speed debuff to everyone else, and there are four Pokémon attacking it in one turn, meaning you'll be stuck sitting through as many as '''16''' unskippable "X's Speed fell!" text boxes per turn, four times each on all four raid members. It gets worse if you're unlucky to get saddled with someone who uses a multi-strike move on Eldegoss; Cotton Down will activate on each individual hit of the move, creating ''even more'' text boxes. You ''will'' want to bring in as many Pokémon immune to Cotton Down as you can, because the alternative is signing yourself up for the Pokémon equivalent of (quite literally) watching grass grow.

* Trying to catch practically any Legendary Pokémon will make them this. Knocking out a Legendary is easy, catching one is an exercise in frustration as they all have the lowest catch rate possible and you have to sustain continued attack from their moves while trying to catch them. It is not unusual to go through up to 30 Ultra Balls and Timer Balls or cause the Legendary to run out of PP causing them to faint from Struggle as the RandomNumberGod proceeds to not let you catch them. The only real exceptions are Legendaries that are plot mandatory to catch plus the Gen VII Mascots in ''Ultra Sun And Ultra Moon''. Of special note is Giratina in ''Platinum'', which has a measly total of ''30 PP'' across its entire moveset because it has three moves with only 5 PP. This means that after it moves 30 times, it will basically immediately Struggle itself to death. If it's at 1 HP exactly, you have a 3% of catching it per Dusk Ball. Good luck.
* Erika from ''VideoGame/PokemonRedAndBlue'' can qualify as this, with two of her three Pokemon knowing the Wrap/Bind moves (which, back in the day, did continuous but light damage over the course of 2 to 5 turns) and two of them using [[StatusEffects the status-inflicting Poisonpowder and Sleep Powder]]. Wrap/Bind was obnoxious because it forced the player's Pokemon to stay in for however many turns it lasted for, all just to do a pittance of damage. And while Poison and Sleep are easily cured with Antidotes and Awakenings, it forced the player to waste a turn dealing with the status. This could make Erika very annoying if the player's Pokemon were unable to take hers out in one shot.

* Deoxys in ''Omega Ruby'' and ''Alpha Sapphire''. Before you can even encounter it, you have to go through capturing Rayquaza, battling [[spoiler:Zinnia]] (who can be defeated in two minutes), and sitting through several minutes of cutscenes, all without saving. Once you finally get to Deoxys, it's a pain if you're trying to capture it. Deoxys is so strong that it can easily obliterate your Mega Rayquaza in one hit with Psycho Boost, and Hyper Beam can deal some serious damage atoo. Then it starts spamming Cosmic Power to buff its defenses and Recover to heal any damage you can deal to it. And if that's not all, it also has an abysmally low capture rate and just will not let itself be captured. If you didn't use your Master Ball, there are two options: KO it and return later[[note]][[GuideDangIt there's no indication]] it won't be lost if you knock it out, and trying again requires you to re-enter the Hall of Fame and return to Sky Pillar[[/note]], or despair endlessly trying to capture it the first time around. Remember: you have to sit through ten minutes of battles and cutscenes before you can fight Deoxys.
* Primal Groudon from ''Omega Ruby/Alpha Sapphire'' is not especially hard to defeat, but catching it is extremely tedious. Fire-Ground, as a type combination, has precisely two weaknesses out of seventeen types. One of those is Water, which is cancelled by Groudon's ability and, if you have means to subvert that ability, would likely kill it dead instead of weakening it appropriately. And when you do weaken it... It knows Rest. Which restores all HP. So basically, if you want to catch it, you have to weaken it about ten times over. And unless you have a Ground type on hand (and Primal Groudon has a ''very'' high Defence stat, which most Ground moves would go up against), you're going to be doing normal damage to it at best. As said, making P. Groudon weak is doable. ''Keeping'' it weak is a headache. Like any Rest-abuser, moves like Worry Seed and Heal Block will stop it being able to heal... but those are moves with very specific applications, and even if you have a Pokemon that can learn them there's a very reasonable chance you simply don't have them learned right that moment.

* Out of all the potential Max Raid bosses, the title of most tedious to fight has to go to Cotton Down Eldegoss. While Eldegoss isn't strong enough to be that dangerous offensively, or quite durable enough to stall out the 10-turn limit like other defensive nightmares like Obstagoon and Shuckle, Eldegoss manages to make itself a total pest on a meta level with its Cotton Down ability. Cotton Down is an ability that activates every time Eldegoss is hit by a damaging move, which gives off cotton spores and lowers the Speed of everything except itself, the goal being to drag everyone else down to its molasses-like Speed tier. This by itself is just mildly annoying and not that bad, but seeing this in action is when the math of it being on a Max Raid boss really hits you: Its ability activates ''every'' time it gets hit, it gives a speed debuff to ''everyone'' else, and there are four Pokémon attacking it in one turn, meaning you'll be stuck sitting through as many as '''16''' unskippable "X's Speed fell!" text boxes per turn, four times each on all four raid members, and that's assuming you weren't unlucky enough to get stuck with AI Jolteon or Maractus[[note]]Jolteon knows Double Kick, which will activate it for both hits if it uses it, and Maractus knows Pin Missile, which can activate it up to ''5'' times, adding up to '''20''' of these text boxes by itself[[/note]]. You ''will'' want to bring in as many Pokémon immune to Cotton Down as you can, because the alternative is signing yourself up for the ''Pokémon'' equivalent of (quite literally) watching grass grow.
* The Forces of Nature in ''Videogame/PokemonLegendsArceus''. For starters, they're surrounded by a small storm that has to be dispersed with a thrown items before you can catch or battle them, though it doesn't stay down for long. But they also fly around the area at a breakneck pace as soon as they spot you, making it difficult to aim items or catch up with them, and they're also generally found in areas that make stealth difficult and that also other wild Pokémon are in, including Alphas, who will all proceed to interfere with your attempts at capture. They can also all block your way with tornados, and if Enamorus hits you with one it'll cause confusion and throw off your inputs. Tornadus and Thundurus are also only found during specific weathers.

* Lugia in [=HeartGold=] and Ho-Oh in ''[=SoulSilver=]'' learn the move Safeguard at level 65 (which blocks status effects for five turns), and are encountered at level 70. Because of this, you can count on them to spam it throughout the fight, especially later on once they've run out of PP for their attacking moves. This makes putting them to sleep or paralyzing them far more difficult, driving down their already low catch rates.

* The Forces of Nature in ''Videogame/PokemonLegendsArceus''. For starters, they're surrounded by a small storm that has to be dispersed with a thrown items before you can catch or battle them, though it doesn't stay down for long. But they also fly around the area at a breakneck pace as soon as they spot you, making it difficult to aim items or catch up with them, and they're also generally found in areas that make stealth difficult and that also other wild Pokémon are in, including Alphas, who will all proceed to interfere with your attempts at capture. They can also all block your way with tornados, and if Enamorus hits you with one it'll cause confusion aand throw off your inputs. Tornadus and Thundurus are also only found during specific weathers.

* In ''Black 2'' and ''White 2'' in the Pokemon World Tournament: Winona, specifically her Altaria. While most of the gym leaders will either give you an even battle or [[ThatOneBoss or just murder you outright]], Winona's Altaria seems designed specifically to cause hair pulling. Of it's four moves, only ''one'' is damaging (Dream Eater) and it only works when your mon is sleeping. The others put your Pokemon to sleep, preventing them from attacking and making them vulnerable to Dream Eater (Sing), recover health (Roost, and also Dream Eater if it works), or boost Altaria's defense (Cotton Guard). So a typical battle has her put your mon to sleep with Sing, heal any damage you may have done with Roost, and then bulk up with Cotton Guard and proceed to use Dream Eater until your Pokemon wakes up, in which case you had better hope you get a Super Effective Critical Hit before you get put to sleep again. It's not quite ThatOneBoss, because unless your mon is extremely vulnerable to Dream Eater, Altaria can't cause much damage, but its moveset seems basically designed to drag the match out as long as possible and make you waste all your good moves trying to KO Altaria before it can heal itself.

** In the remakes, Flint's Drifblim knows Minimize and ''Baton Pass.'' Meaning once he maxes out on evasion, he'll then pass the boosts to [[SignatureMon Infernape]] and be incredibly frustrating. He also knows Will-o-Wisp and Strength Sap for both crippling your team and maintaining longevity. Thankfully, the move Taunt will render him useless. However, he can be a difficult curveball for the unprepared player, especially one who doesn't have knowledge of competitive play.

* Primal Groudon from ''Omega Ruby/Alpha Sapphire'' is not especially hard to defeat, but catching it is extremely difficult. Fire-Ground, as a type combination, has precisely two weaknesses out of seventeen types. One of those is Water, which is cancelled by Groudon's ability and, if you have means to subvert that ability, would likely kill it dead instead of weakening it appropriately. And when you do weaken it... It knows Rest. Which restores all HP. So basically, if you want to catch it, you have to weaken it about ten times over. And unless you have a Ground type on hand (and Primal Groudon has a ''very'' high Defence stat, which most Ground moves would go up against), you're going to be doing normal damage to it at best. As said, making P. Groudon weak is doable. ''Keeping'' it weak is a headache. Like any Rest-abuser, moves like Worry Seed and Heal Block will stop it being able to heal... but those are moves with very specific applications, and even if you have a Pokemon that can learn them there's a very reasonable chance you simply don't have them learned right that moment.

** About the only thing keeping the Gigantamax forms of Pikachu and Eevee from being ThatOneBoss is that, not being fully evolved, their defenses are paper-thin. However, they both tend to run essentially the same strategy of trying to stop the player's side from getting to attack at all. G-Max Pikachu's signature move, G-Max Volt Crash, paralyzes the entire party, including Ground-types that the attack itself can't even hit, and then spams Double Team to try and make sure any Pokemon that do get to move will miss anyway. G-Max Eevee manages to be just as annoying; its signature move, G-Max Cuddle inflicts infatuation on any opposing Pokemon of the opposite gender from Eevee itself, forcing them to stand by and do nothing 50% of the time, and as salt in the wound, Eevee also comes knowing Sand-Attack to lower the player's accuracy even further and ''Endure'', a move that guarantees itself a LastChanceHitPoint for a full turn, dragging the fight out even more.

* Erika from ''VideoGame/PokemonRedAndBlue'' can qualify as this, with two of her three Pokemon knowing the Wrap/Bind moves (which, back in the day, did continuous but light damage over the course of 2 to 5 turns) and two of them using [[StatusEffects the status-inflicting Poisonpowder and Sleep Powder]]. Wrap/Bind was obnoxious because it prevented switching and forced the player's Pokemon to stay in for however many turns it lasted for, all just to do a pittance of damage. And while Poison and Sleep are easily cured with Antidotes and Awakenings, it forced the player to waste a turn dealing with the status. This could make Erika very annoying if the player's Pokemon were unable to take hers out in one shot.