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1[[GottaCatchThemAll Catching 'em all]] would be a lot easier if it weren't for [[ThatOneLevel these levels]].
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4[[foldercontrol]]
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6[[folder:Gen I and Remakes]]
7* Rock Tunnel. You need Flash to get through it, and it's full of ComMons like Geodude and Zubat. It's just a minor thing, but it's a maelstrom of GoddamnedBats.
8* Silph Co., an enormous, 11-floor skyscraper with a maze-like layout, confusing teleporters, half the dungeon hidden behind locked doors, and no hint as to the location of the Card Key and the teleporter leading to Giovanni. Absolute hell for a first-time player. It's made worse by how, out of all the teleporters in the entire area, there's only ''a single one'' that is actually necessary as every single other one takes you to an area that's either already reachable or behind a keycard door and said keycard can be found without ever using a teleporter -- they're basically there to [[TrollingCreator ensure a first-time player spends about three hours miserably groping around this pointless labyrinthine nightmare]] rather than [[GuideDangIt going straight for the keycard and then trial-and-erroring every teleporter behind a locked door until they find the one that takes them to a new area]].
9* Seafoam Islands. If you want to catch the legendary Articuno, you have to travel through the underground caves. However, Articuno is located in a part of the caves only accessible by Surfing on water where the current is extremely fast, so you can't Surf normally until you use Strength to drop boulders through holes into the water, which will change its flow and slow the current.
10* The Pokémon Mansion. A huge [[SurpriseDifficulty jump in wild Pokémon levels]], a storm of GoddamnedBats, and [[DemonicSpiders Raticate and Weezing or Muk await to make your life hell.]] [[YouWillNotEvadeMe Raticate's high speed will deny your escape]] and, despite their low defenses, they WILL ZergRush you, [[TakingYouWithMe whereas Weezing will constantly Selfdestruct]], likely taking away a large chunk of your party's health. [[StoneWall And Muk...good luck killing it]] if you don't have a [[GameBreaker high-leveled Psychic-type that knows Psybeam and/or Psychic.]] Even worse, the level [[RidiculouslyDifficultRoute is a FREAKIN' MAZE]]. But it's a required dungeon, as the key to enter the Cinnabar Gym is hidden inside.
11[[/folder]]
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13[[folder:Gen II and Remakes]]
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15* [[http://bulbapedia.bulbagarden.net/wiki/Mt._Mortar Mt. Mortar]] is the largest cave in the entire series. It's basically an enormous [[MalevolentArchitecture maze]], it's pitch-black inside, it has countless [[BlockPuzzle Strength puzzles]], and, to top it all off, it has the highest possible [[RandomEncounters Pokémon encounter rate]], so when you inevitably get lost you'll spend five times as long getting out as you would otherwise. What's especially annoying is the whole point of going into Mt. Mortar is to get a rare Pokémon, but if you have all six party spots full by the time you reach the end, you have to leave, ditch the extra Pokémon, then ''go through it again''. [[GuideDangIt But the game doesn't tell you that until you actually get to the character who gives it to you. In fact, the game doesn't even tell you that you'll get a rare Pokémon by entering the mountain.]]
16* Johto Route 40-41. Most likely, it's the first time you'll be sailing/surfing on your Pokémon, as Cianwood City Gym would be your next gym after Ecruteak. On your way, you'll be facing Tentacools and Tentacruels, whose moves are likely to poison your Pokémon, requiring lots of antidotes and/or potions to be manageable. Repels may not necessarily work either, as there are Tentacruels which can go up to level 29, which is rather high for this stage in the game. [[note]]For reference, all of the swimmers' trainer battles on the way are mostly around 18-23. Eusine's Pokémon in the Cianwood City event battle are around 25 at the most. Chuck's Pokémon for the gym battle are 27-31.[[/note]] And this is in addition to any trainer battles you make along the way. At least, once you beat Chuck, you'll now have the option to fly straight back to Olivine City.
17* Whirl Islands, for those who are trying to find and capture Lugia. If going in without a map or prior knowledge, you will likely get lost in the maze-like structure. It doesn't help that the islands have multiple entrances and only one of them takes you to Lugia.
18* The Ice Path, between the ice sliding and pushing boulders through holes and more ice...
19* Mt. Silver from HGSS. The original version was a short cave with only three rooms, whereas this revamp takes inspiration from Mt. Coronet and requires Rock Climb to ascend. While Rock Climb is a fairly decent move as far as [=HMs=] go, it still means that you have to face the TrueFinalBoss with an [[JokeCharacter HM Slave]] in your party unless one of your mainstays has it. Though it's still an improvement on the original games, where you needed one of your Pokémon to know ''Flash'' to make it through the first room.
20[[/folder]]
21
22[[folder:Gen III and Remakes]]
23* The cracked floor in Dewford Cave is very annoying, especially since you have fairly narrow areas to steer through. Thankfully, this part of the cave is completely optional (and, if it's the first time you've played the game, you might not even think to go back there).
24* Some of the Trick House puzzles are noteworthy for being tricky to surpass, such as the rotating door maze and the arrow floor maze, using the same mechanics as Fortree and Mossdeep Gym.
25* Route 111's desert may not be ''difficult'', but it sure is frustrating. There's a permanent sandstorm, causing non-Rock, Ground, or Steel-type Pokémon to take chip damage every turn. Most of the Pokémon (wild and trained) have accuracy lowering moves, including Sandshrew and Sandslash, who have high Defense and ''also'' come with Sand Veil to make hitting them even more difficult. Additionally, if you encounter a wild Trapinch, it has a 50% chance of having the Arena Trap ability, meaning you're unable to run away and ''forced'' to make it faint if your lead Pokémon isn't airborne.
26* Wallace's cracked ice gym puzzle. Step on every tile to open the stairs to the next platform; step on the same tile twice and you fall through the floor. Fall through the floor and you have to repeat whatever puzzles you've already solved. Made significantly easier in the remakes.
27* The Sky Pillar, Rayquaza's roost. To navigate to where the dragon waits, you have to use the Mach Bike and do everything exactly right in regards to speed and sharp turns to get across the floor before you fall through it, and the resident Claydol, Altaria, Banette, and Sableye are no pushovers. And there's even a puzzle sneaked in - in one particular floor, the only way to advance is by falling down a floor, and you need to know where to stop so you can fall into the right spot. It's completely optional in Ruby and Sapphire, and while Emerald makes it a required area, the wild Pokémon are much weaker and the required climb doesn't have any pitfalls in your way. In the remake, they remove this challenge and instead give you an InfoDump.
28* Route 134, where the sunken area for the Regi sidequest is at. You have to watch the currents and try not to miss the small square, or fly back to Pacifidlog Town and do it all over again. Getting to all the trainers and items on the route is just as big a pain.
29* Victory Road in these games is generally considered up there with 4th Gen's and [=BW2=]'s as one of the hardest in the series. It's [[MarathonLevel long]] (the average LetsPlay takes around ''one and a half hours'' to get through it), requires Surf, Waterfall, Flash, Strength, and Rock Smash and is filled with tough trainers (and in Emerald, there's one Pokémon that uses [[MyRulesAreNotYourRules a move it can't normally learn]]). And at the end (Ruby, Sapphire, and ORAS) or beginning (Emerald) you have to fight Wally...who's taken a major [[TookALevelInBadass level in badass]] since you last saw him.
30[[/folder]]
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32[[folder:Gen IV and Remakes]]
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34* The northern parts of Route 210 (and part of Mt. Coronet) that feature fog. Fog lowers the accuracy of every Pokémon on the field, causing every battle to be extended by a good few minutes while you wait for your Pokémon to actually land an attack. Add to this the fact that Defog is just about the most useless HM ever [[note]]This changes in the competitive scene in Generation VI after it stops being a Hidden Machine, as it was modified to disable entry hazards like Stealth Rock and Spikes on both sides of the field.[[/note]] (and only Pokémon with wings can learn it, preventing you from giving it to common HM slaves like Bibarel).
35* The muddy terrain around Pastoria and inside the Great Marsh. There's a good chance of getting stuck when walking into a marsh tile, in which case the player must press different directional buttons repeatedly to become unstuck. This has to be done at practically ''every single step''. As if that wasn't excruciatingly slow enough, each of those little wiggles to free oneself can result in a wild Pokémon encounter. And ''even worse'' is that, while ''Platinum'' took mercy on players by making the deep parts of the bog slightly darker, they were completely indistinguishable in ''Diamond'' and ''Pearl'', so players just had to blindly guess their way through the areas.
36* Routes 216 and 217, especially 217. Lots of ice types, long distances, perpetual hail, the necessity of pushing through Mt. Coronet to even get there, and in the case of 217, a straightforward blizzard that makes it virtually impossible to see what you're doing or where you're going beyond "Snowpoint is ''up''". Then, just for giggles, remember that the first two games in this series had ''only one Fire type'' that could be caught in the wild prior to completing the main game.
37* Candice's Gym is just ridiculous. It's a big icy pit where you have to slide down towards the center while building up enough momentum to smash through the snowballs at the bottom. But there are trainers, snow patches, and stairs positioned just right to prevent you from just, y'know, ''sliding down normally''; instead you have to circle around the gym finding the most obtuse paths possible to get enough momentum. It's not unknown for first-time players to spend up to an ''hour'' solving this puzzle. Not helping is the fact that in ''Brilliant Diamond'' and ''Shining Pearl'', it's possible to accidentally softlock yourself in this gym if you get diagonal movement ''just'' wrong, sticking yourself in the lowest pit surrounded by snowballs you now can't break.
38* Victory Road, while not difficult to complete (and actually rather simple if you're not interested in all the trainers and items), requires Surf, Waterfall, Rock Smash, Strength and Rock Climb. If you want to complete the post-game section with Marley, you're probably bringing Defog as well.
39[[/folder]]
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41[[folder:Gen V]]
42
43!!''VideoGame/PokemonBlackAndWhite''
44* Pinwheel Forest. The sign outside more or less says "Pinwheel Forest: Hope you remembered some Antidote."
45* Chargestone Cave. The wild 'Mons are annoyingly tough (Boldore has a LastChanceHitPoint ability but thankfully can't explode at the levels it's found here; Joltik can prevent you from using Berry items and can slow you down with Electroweb; Klink is Steel-type and will whack you with Gear Grind, which hits twice; Ferroseed, which on top of being a StoneWall with only two weaknesses has an ability that costs you health every time you hit it; and Nosepass in the sequels, which is even more of a StoneWall, also has Sturdy, and prevents fleeing if the active 'Mon is a Steel-type). While most of them are slow enough that running away is easy, there will be a lot of encounters, and they will get very annoying very quickly. The cave is ''long'' and packed with Trainers. Also, the Doctor trainer is located somewhat off the beaten path. At least he's right before the start of the Team Plasma gauntlet, making healing much more convenient.
46** The worst part is Tynamo. Whether you're a {{Hundred Percent Completion}}ist looking to complete the PokéDex or you just want to have a [[MagikarpPower devastatingly strong]] [[PsychoElectricEel Eelektross]] on your team, the game doesn't make it easy. There is a 1 in ''50'' chance of this mon appearing unless you go to the bottom floor, in which case it's 1 in 12, but of course, going to the bottom floor is quite annoying in itself. On top of which, while Tynamo's final form may be monstrously strong, its base form has weak defenses, so good luck weakening it without False Swipe.
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48!!''VideoGame/PokemonBlack2AndWhite2''
49* The Driftveil Gym proves that combining TheMaze with a BlackoutBasement is extremely annoying. And the gym leader himself is ThatOneBoss.
50* The World Tournament can turn into this because you cannot predict which Gym Leaders you'll face, and it's hard to get type coverage for everything out of just three Pokémon.
51** One of the worst is the Kanto Leaders tournament. If you want to access all the other tournaments, you have to beat the first five regions' leaders, which turns them into brick walls. The worst part is that the Gen I (and the cross-generational evolutions of them) mons they use are ''strong.'' Lt. Surge's Electrode, Giovanni's Rhyperior, Misty's Starmie...they're all very nasty. And conveniently hold items that dampen your attacks or boost their one stat/move you were trying to use to get through them/don't want to be hit with. Unlike the other regions' Gym Leaders, their type specialties rarely share a common weakness, so your team would be more likely to be disadvantaged in either round.
52** The Mix/Mix Master Tournaments, which are similar to the rest of the tournaments...but the twist is, a random mon of your team and the opponent's team is switched. Your GameBreaker isn't so awesome when it's going against you, huh? Plus, you have to figure out how to work with the mon you received, which is a challenge in and of itself. A fun challenge, but still brutal.
53%% ZCE** The less said about the Champions' Tournament...[[SNKBoss the better.]] Needs more context
54* Black Tower/White Treehollow. The first half is fine, but after Area 5, all the areas have multiple floors for you to search through to find the gate boss. And you can't use items from your bag (though your Pokémon can hold berries or herbs or battle items). There are nurses scattered about, but remembering where they are can be tricky. Also, by the end, everyone's using level 70 and above Pokémon, including the Legendary Bird trio. Look out for their OHKO moves like Articuno's Sheer Cold. Thankfully though, it's open level and OlympusMons are allowed.
55* Though most of the main game is light on these areas, Victory Road has one tricky area. The trainers there use Pokémon at Levels 54 and 55 (and on Challenge Mode, ''58 and 59''), which is higher than the levels Ghetsis and Colress had in the Plasma Frigate that you just harrowed through. And nearly all of them, especially Veterans and Ace Trainers, have move sets on their Pokémon that often provide wide type coverage and can sneak up on you if you're not prepared for them. In addition, there are ''seven'' different areas that you can catch wild Pokémon in, and types including Ghost, Grass, Flying, Rock, Water, Fighting, Ground, Rock, and Dragon. And in the thick grass, they come out at Level 52-55, which tops at ''one level'' below what the Elite Four are packing. To put that in perspective, you could catch yourself at least half a team's worth and use that against the Elite Four. Finally, you have to fight your rival at the very end, and while he only has four Pokémon, they're four ''powerful'' Pokémon, especially his bulky new Bouffalant. This place may honestly be just as hard as the Elite Four and Champion themselves. The only mercy is that there's a Doctor not far in who will heal your Pokémon free of charge if you can beat his Clefable (that likes to be stupid with Minimize), although if you're deep in, it might be an unpleasant walk back to him unless you have Fly to return to the entrance.
56* Match 14 of the Battle Subway, on the regular lines. Before, you've been fighting unevolved Pokémon with a few singly-evolved ones and maybe a couple of weaker fully-evolved ones. Suddenly, the Trainers start throwing [[DemonicSpiders the Elemental Monkeys and Basculin]] at you, and pack other strong fully-evolved mons. Considering this is right at the end of a good winning streak, it hurts even more to lose. Then if you somehow win, you have to go through even ''more'' of Trainers like these. Then once you somehow beat the Subway Boss, you unlock the Super ___ Train, which consists of nothing but fully-evolved Pokémon from all generations.
57[[/folder]]
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59[[folder:Gen VI]]
60* The Reflection Cave is the first cave with random encounters (The Glittering Cave has a certain amount of wild Pokémon that are scripted to come out). There are tons of dead ends, and the worst part is you can find wild Wobbuffet here. All Wobbuffet have the ability Shadow Tag, which prevents any non-Ghost-type Pokémon from fleeing the battle or switching out. Its HP happens to be incredibly high enough that Wobbuffet can easily survive and it can use Counter and Mirror Coat to inflict double damage from physical and special attacks respectively. And the majority of the trainer in Reflection Cave cannot be avoided because they're facing at the mirrors, so they will see the player passing by behind them. This place can become a nightmare.
61* Route 13 is this in SPADES. On the plus side, there are no random encounters. However, they're replaced by digging Pokémon that move in erratic fashion, follow you relentlessly and are immune to repels. Combine that with an easterly wind that slows you down to a crawl (regardless if you walk, run, or use the Roller Skates or Bicycle), and those diggers are nigh unavoidable. And for navigation...well, it's not bad if you're just traveling between Coumarine City and Lumiose City. But have fun finding the Kalos Power Plant, and may Arceus help you if you're brave (or foolish) enough to go hunting for items. And that's not all — it's the only place in the entire game where you can evolve Magneton and Nosepass, so if you want Magnezone and/or Probopass on your team or just want to complete your Pokédex, you'll HAVE to return. At least one player has wondered why the Kalos government hasn't just carpet-bombed the entire route. What doesn't make things any better is that the encounters are mostly Dugtrio and Trapinch, both of which sport the infamous Arena Trap ability. Better lead with a Ghost-type or a Flying-type when going through the route. Or catch a Pokémon that has the "Run Away" ability.
62* While it's a bit strange for a ''city'' to be this, Lumiose City is easily one of the most hated areas of the game. Absurdly awkward camera angles make it very hard to see where you're going, the circular design makes all of the features seemingly blend into each other, there are few landmarks apart from the central tower, and everything looks almost exactly the same. Unless you use the Taxi system or have the patience to roam around the city long enough to get used to its design, finding anything other than the first Pokémon Center and Sycamore's Lab is an exercise in frustration, looking around seemingly everywhere with very few hints. It's also entirely possible to walk right by your destination without even noticing due to the camera angle. If you want access to the boutique, you need to visit every single place in the city - LastLousyPoint doesn't even begin to describe it. Sometimes, it's easy to wind up in the wrong building, especially through the error of slightly nudging yourself into the wrong door. And if all of this wasn't enough, there was a GameBreakingBug (now with available patch) where if you saved outside in the wrong place, it can permanently freeze your game and was hard to fix, as described [[http://www.gamefaqs.com/boards/696959-pokemon-x/67488169 here]].
63** The Post-Game has you going back and forth all over the city looking for lost Pokémon, thieves, and the like hidden all over the place. They are at three tricky to find alleys that you have to backtrack to multiple times, and which you cannot Taxi to.
64* Laverre Gym. It's another teleporter maze. In addition, the gym's specialty type is brand-new, so new players may not know how to deal with the Pokémon the trainers and Valerie have, and are decently high-leveled.
65* Route 20, or the Winding Woods as it's also referred to as. It's another forest, and when you go forward, should you attempt to go back through the same entrance, chances are you can end up in a completely different part of the forest from where you came in. This can make attempting to find certain parts of the area frustrating. What's even worse is that it's a pretty good location to grind your team in...if you don't mind all of the wild Level 50 Amoonguss that like to spam Solar Beam and Synthesis, and can status you with Effect Spore should you use contact moves against them.
66[[/folder]]
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68[[folder:Gen VII]]
69* The second visit to [[spoiler: Aether Paradise]]. The trainers have high leveled Pokémon, many fighting you in a row with no break to heal. Backtracking to heal and stock up on supplies is also rendered a pain by the size of the place. And to top is all off is two bosses that qualify as ThatOneBoss.
70* Vast Poni Canyon might not be named Victory Road but it does have all the required elements to be one. It is just as long as past Victory Roads (maybe even longer), full of tough trainers and wild Pokémon. There are also a lot of branching paths, some can be difficult to spot and most need a Poke Ride to go through. It also begins with a boss against Kahuna Hapu, whose highest levelled Pokémon are level 48, (trainers before and after her are in the mid forties) and ends with a trial against the region's Dragon psuedo-legendary (which is thankfully capable of being rendered anticlimactic). Then you have to face the BigBad and the Mascot Legendary. The only relief you get is periodic heals from Lillie.
71** ''Ultra Sun and Ultra Moon'' remove Hapu's battle at the start but make up for it by beefing up Totem Kommo-o to the point it could be considered ThatOneBoss. And you also have to deal with [[spoiler: Ultra Necrozma]] when finished though the appearance of a fly point does make it possible to stock up.
72[[/folder]]
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74[[folder:Mystery Dungeon]]
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76* Purity Forest, Celebi's domain. It's 99 floors long, you can only bring one Pokémon, said Pokémon is reduced to level 1, and all of your money and [[BagOfSharing toolbox]] contents are destroyed. You're pretty much at the random generator's mercy here. At least you don't have to ''fight'' Celebi at the end.
77** While not as bad, there's also Western Cave. 99 floors, no food items outside of Kecleon Shops, and Tyranitars swarm the middle floors and activate Sand Stream. This dungeon will throw everything at you, including the kitchen sink, if you aren't high-leveled. And your reward for making it to the last of those 99 floors? Mewtwo [[spoiler: (who should be a complete joke compared to some of the bosses you've faced, especially after making it past those previous 98 floors. Also, he won't join you the first time. That's right, you have to go through the cave a SECOND time to recruit him]]. But on the plus side, the wild foes give LOTS of EXP points. Expect to gain at least ten levels per one go through to the end.
78** In the main story mode, Sky Tower can be a tough climb. Early floors have you dealing with ghosts, who can travel through walls and attack your Pokémon there, while most Pokémon cannot attack into walls. There are also floors that activate different weather, including Hail, which drains your health faster than you can heal it off, forcing you to scramble for the exit. Enemies also start getting nastier, featuring lots of enemies with the PP-draining Pressure ability, foes like Venomoth who use Silver Wind to hit anyone in the same room as it, and Aerodactyl, who can use not only Supersonic to confuse you, but also Agility to make ''all the enemy Pokémon in the same room move at double speed''. And in these later levels, it isn't uncommon to stumble into a Monster House, which dumps ten or so Pokémon at you all at once. [[HoldYourHippogriffs Arceus help you]] if two or more Aerodactyl drop in, as their combined Agility will mean you'll be ganged up on all sides by Pokémon moving at quadruple speed while Venomoth in the back spam Silver Wind on your team. Then comes Sky Tower Summit, which, while only 9 floors long, spawns no food ''at all'' and has complicated layout which makes finding stairs a luck-based mission.
79* Aegis Cave in ''[[VideoGame/PokemonMysteryDungeon Pokémon Mystery Dungeon]] [[VideoGame/PokemonMysteryDungeonExplorers Explorers of Time/Darkness]]''. It's not a hard dungeon-- there are ample Oran Berries and the Unown aren't that tough at all. But you have to find stones that Unown drop, of their own letter-shape, to spell out I-C-E, R-O-C-K, and S-T-E-E-L. Not every type appears, and even then, the stones are dropped maybe a quarter of the time. And you have to keep repeating a three-floor section until you get all the letters you need so you can go on and fight the appropriate Legendary Golem (who, thankfully, aren't that tough). And, you can't save in between, so you HAVE to do this all in one go. Fortunately, much of the annoyance can be simplified, thanks to an inherent quirk of the Legendary Golems. Simply put, bring a Fighting type.
80** ''Explorers of Sky'' brought us the ultimate dungeon: Destiny Tower. Like Purity Forest, it has 99 floors, you're only allowed to bring in your leader and its level will be lowered to 1, and you're not allowed to bring in any items or money. It also prevents you from using your IQ skills [[note]] which keeps Reviver Seeds from activating thanks to no Item Master[[/note]], and keeps traps hidden when you step on them. Worst part? Some of these traps are absolute cruelty, with the worst one being the "Grudge" trap, which gives a PERMANENT grudge status to EVERY SINGLE POKÉMON ON THE FLOOR. And for the icing on the cake, unlike Purity Forest, you can't be rescued, so if you're knocked out even one time, you have to start all over again. Good luck getting to the top.
81*** Likewise, Sky has Zero Isle Center. Foes begin at Level 90 and quickly make their way to Level 99 but give no EXP Points whatsoever. Similarly to Destiny Tower, traps only become visible when you step on them, Grudge Traps which give never-ending Grudge status to every Pokémon on the floor, lots of traps and frequent monster houses, only being allowed to bring 16 items, and [[ArsonMurderAndJaywalking some randomly placed Level 5 Pokémon like Clefairy and Togepi on some floors]].
82** Dark Crater. Just when it seems that everything's going fine, suddenly something screws up by either Cresselia failing somewhere, or one of your teammates getting hit by an overpowered move ([[GameBreaker multi-hit moves say hello!]]). At this rate, Reviver Seeds are important, but suddenly there is none of these for a lot of levels.
83** Dark Hill is this if you are a Normal-type Pokémon, as your normal-type moves do only 1/4 damage to ghosts, which comprise the majority of the Pokémon there. Plus, several Pokémon have Spite, which will remove all of the PP of the move last used, just in case you have any dark-type moves. Finally, [[DemonicSpiders Dusclops]] know the move Curse, which is nigh impossible to survive without an Oran Berry. Did we mention this place has ''15'' floors?
84** Similarly, if you or your partner is a Fire type, Surrounded Sea will royally screw you over. And it has ''20'' floors. Really, any dungeon that has an overall type advantage against your team turns into one of these.
85* [[spoiler:The Great Glacier (first visit)]] in ''Gates to Infinity''. It's especially brutal for being right in the mid-game. First off, it's got ''[[MarathonLevel 14]]'' floors; for reference the gauntlet leading up to final boss is 29 floors in total, and ''nothing but'' the {{Brutal Bonus Level}}s go above 30 floors. Second, some floors have Hail active, which not only disables passive healing but does slight but steady damage over time, and nobody you have is immune to it. Third, you're stuck with a limited selection of party members, one of which [[TheLoad isn't very strong]] (and newly-recruited members are sent right off to Paradise, so no additional team building). Fourth, if the hail wasn't bad enough, the place is infested with Yamask and Trubbish, which will burn and poison your team, sapping their health even more (and poison disables passive healing even on the floors without Hail). Trubbish is especially bad, as it's got lots of health and it can prevent you from attacking if you hit it. And finally, it's right after a 10-floor dungeon [[spoiler:(Telluric Path)]] filled with more annoying enemies. To make things worse, you can't leave the dungeon at any time. You better pray you find a Pure Seed (which warps you to the stairs) for those Hail floors...
86** Not long afterwards is the Forest of Shadows, for several reasons. What's the biggest? ''[[MultiMookMelee MONSTER HOUSES]].'' This is the first dungeon that includes Monster Houses, and they're quite brutal. End up wandering into [[ShmuckBait a room full of treasure]] and you're assaulted by 10 or so strong Pokémon at once while an Archeops in the back spams Agility (double speed for everyone!) There's also a good chance you'll step on a trap when you immediately enter; if it's a Sleep trap, you're screwed. If you don't have any Petrify or Sleep Orbs on you, you're good as dead unless you can pull off a Team Attack right then and there. And if you're really unlucky, it's possible that the only way through a dungeon is ''through a Monster House''. It's also a 14-floor dungeon with weather effects, though thankfully it's only Rain. Still disables passive healing and weakens Tepig's more powerful moves, but at least it doesn't damage you like Hail. You also can ''only'' take two party members: yourself and your partner. The local mons are quite annoying: Vaporeon has lots of health and will spam Sand-Attack, Tail Whip, and Aurora Beam (which can lower your attack), and are immune to Water-type attacks. Druddigon are quite strong and can randomly hurt you when you hit them. Archeops are thankfully sleeping outside Monster Houses but are so powerful they need [[PowerLimiter the Defeatist Ability]]. Conkeldurr is very strong and can boost its Attack if burned or poisoned. It's also right at the beginning of a long gauntlet of dungeons (although you can switch to Companion Mode to have them obtain items if needed).
87** Withering Savanna. Good news: you picked up a [[spoiler:[[GuestStarPartyMember level 64 Hydreigon]]]] from the last dungeon! Bad news: this dungeon is full of [[DemonicSpiders Lilligant]] that spam Teeter Dance (which confuses ''the entire room''.) Your ally isn't so useful when he can't even hit anything - or you can't hit anything, for that matter. It's also a 17-floor dungeon. Of course, have the Prevention Team Skill, or a couple of Persim Bands, and you're fine.
88** The Worldcore, in which you must play as your partner solo in the postgame in order to [[spoiler: get you to come back to the Pokémon World.]] It is basically every enemy similar to [[spoiler:Munna's gang]] in the dungeon. Whirlipede can and will eat your Reviver Seeds and Oran Berries with its Bug Bite. Munna (similar to the [[spoiler: Munna from the main storyline]]) can use Yawn and Psybeam on you to inflict Sleep and Confusion respectively, and Salamence and Chandelure can seriously hit you hard in the face. And Arceus help you if your partner is a Grass type.
89* ''VideoGame/PokemonSuperMysteryDungeon'' has the Cave of the Deep, which is the third in a string of five dungeons you need to do back to back. It's only 7 floors, but it's chock full of Ditto, and in this game when they Transform it ''confuses your entire party'' other than the Pokémon that it transformed into. They can also [[ChestMonster disguise themselves as items]]. While you have two guests for this dungeon, including [[spoiler:a level 50 Mawile]], that means that the Ditto can potentially destroy you with that Pokémon's moves...if you don't destroy yourselves from confusion, that is.
90** Poliwrath River is a very frustrating early-game dungeon, especially for any Fire or Water type players/partners. The worst offender of the Pokémon living there, however, is Heliolisk with its '''''motherfucking Razor Wind.''''' It uses up a turn to charge it, and once it's executed, it can and will hit you VERY hard, meaning you're gonna need a lot of wands, Oran Berries, and Reviver Seeds.
91** The Submerged Cave, a dungeon that you must get through, has very OP Water types that will give Fire type players/partners a tough time. Filled with Pokémon that will find many ways to KO you, such as rain boosting Water type moves for those enemy Pokémon, your worst challenge is Seadra, who will spam Hydro Pump. You also have a guest Pokémon for this dungeon, so if Seadra takes it out and then evolves into Kingdra, you're screwed.
92** The postgame story has the Sand Dune of Spirits, in which getting there is a must in order to [[spoiler: find Xatu to find out how to bring your partner back.]] However, those who turned into a Charmander, Cyndaquil, Torchic, Chimchar, Tepig, or Fennekin are going to find out just how brutal this dungeon possibly is. For starters, you need to do the whole thing solo, and it is filled with Rock and Ground types that will knock you out in a flash. There are also Growlithe and Houndoom that live here, and they have Flash Fire, which boosts Fire type attacks when hit by another Fire type attack. You need to be careful here, or you will be pounded to dust.
93*** There's a way to do this dungeon with a partner, but your only option is Hoopa. Hoopa cannot be controlled directly, so it may cause more harm than good to have it around. And because it's a Psychic type, Houndoom is bad news for it.
94** Mystery Forest, another postgame dungeon that you must do solo in order to [[spoiler: find Mew]], is far more worse than Submerged Cave. It is chock full of literally Poison types, even Venomoth, which can and will give you a hard time with Quiver Dance and Silver Wind. Ariados will gladly munch away your Reviver Seeds and Oran Berries. There is also Trubbish which will use Toxic Spikes without a care in the entire world. But the worst is yet to come; also living in the forest are '''Haunter''' and '''Vileplume'''! Haunter will spam Hypnosis, and Vileplume will spam Stun Powder and Poison Powder. It can also hit hard with its Grass type attacks if you are a Water type. And if Haunter and Vileplume are together to take you out, you are completely screwed.
95** The Purifying Cave, yet another postgame dungeon in which you need to do in order to [[spoiler:save Mew, who is said to have some of Dark Matter's energy in him,]] is basically like the Worldcore, but ''this'' particular dungeon is a dungeon that forces players who turned into a Grass type or Riolu at the start of the game to use trial and error or be wrecked. There are Psychic types and Ice types, and even Flying types. One example is Future Sight, which will hit Fighting types extremely hard. Also, Ice Pokémon and Flying Pokémon will become a possible threat to Grass types, with Flying types ''also'' hitting Fighting types hard. As an additional warning, one hit from an attack, and you are possibly dead. This means that your ultimate skills are put to the test, so you need to be extra careful. Luckily, you can bring two Pokémon with you, but if you faint, you're a goner, and it is back to the start of the Purifying Cave for you.
96** When you become Gold Rank, the Mysterious Geoglyph becomes available. Another relatively short dungeon, coming in at just 8 floors, but there's a good reason for that. Unlike every other dungeon that features a Legendary Pokémon up to this point, where it's just a regular dungeon with the Legendary at the end (or in some cases, just a fight with the Legendary), this is a dungeon ''where the only enemy is Genesect.'' That's right! The entire dungeon consists solely of Genesects running around blasting you with Techno Blast and Signal Beam. Not to mention they come in all different Drive varieties, meaning even if you come in with a team of all fire Pokémon there's still a chance one can ruin your day if it has the Douse Drive, making its Techno Blast water type. And the last floor has a fixed layout; it's a spiral pattern where you can't just tunnel through the walls and make a beeline for the exit, meaning you have to face all of the Genesect head-on. Having attacks that hit the whole room make this less of a pain, but it's still a doozy.
97** Your "reward" for defeating Mewtwo is the Meteorite Crater, which is the same concept as the Geoglyph but with ''Deoxys'' instead of Genesect. This makes it tougher, due partially to the fact that their ability is Pressure, meaning you'll run out of PP even quicker than normal and you'll probably burn it all on a Deoxys-D tanking all of your attacks. Pray you start each floor close to the stairs. However, the final floor is much easier than the Geoglyph's and doesn't force you to take every enemy head-on.
98** Dragon Gate. What type would you expect to see in a dungeon with this name? That's right, [[BaitAndSwitch Normal and Fairy!]] A lot of the enemies here are pretty bulky, too, and at the end of it is [[SequentialBossFight THREE back-to-back legendary fights.]] It is without mercy the whole way through.
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103* Escorting the bug-phobic mechanic in the first ''VideoGame/PokemonRanger'' game. He freaked out and made you start over if he - or YOU, for some unfathomable reason - touched so much as a single bug. Oh, and you have to escort him through the most bug-infested area of the game, with loads who will either just float around randomly but quickly, or CHASE AFTER YOU - many of the latter being FASTER THAN YOU ARE.
104** That one temple where you have to first fight a Kingdra, Charizard and Flygon and then use Pokémon to get through an irritating maze and THEN fight a Salamence at the end without saving. It's a complete LuckBasedMission, because you can't use your Plusle-- even though Salamence isn't immune to electricity.
105** Hippowdon Temple in the second game. The constant, damage-inducing sand balls were downright obnoxious. It doesn't help that [[spoiler:all that hard work goes to waste since you lose the Yellow Gem to Heath.]]
106** The second time you go through [[LethalLavaLand Boyle Volcano]] is a real pain in the butt. You got lava geysers spraying up from the ground, and Hot Boulders flying around as if launched from invisible cannons. Then there's the tendency of EVERY Pokémon to have some way to attack you and send you flying. And then, if you survive, you have to go up against [[spoiler:Lavana and her [[LightningBruiser Infernape]]]], and then [[ThatOneBoss HEATRAN]][[note]]Think you can you use your brandy Shieldon or nearby Rhydon to stop him from attacking? Nope, Heatran will still summon these lava pools.[[/note]].
107** In the third game, Mt. Sorbet. Most of the level is fine, but then you get to the part with the avalanches. Every few seconds, there is a long drawn-out cutscene where an avalanche happens. You have to be behind a big pillar to shield yourself from the avalanche, or you'll be back at the bottom. The game is picky about whether you're behind it or not. It doesn't help that the game slows you down in these areas. And there are two of these areas. And you will probably come back to that area again. Also, Mt. Layuda, specifically the parts where all the agitated Electric Pokémon are attacking you so you fall into the pits and also a section similar to Mt. Sorbet where you have to cross a pool of water that is constantly being electrified by lightning and if you're not standing on one of the patches of land you'll get electrocuted and take damage.
108** There is also Oblivia Ruins in Guardian Signs: the level itself is OK, [[StealthBasedMission but there is a part where you must try to get to the next room without the Claydols catching you to progress or you'll be sent back to the start of the room.]] The Claydols, unlike the Dusclops in the forest, can't be captured to get them out of the way as they have a 360º vision, so you can't go behind them, which makes them rather hard to avoid. To make matters more frustrating, in the first visit there are places where you require Poké Assists for Target Clear in the middle of the Claydol room. Not to add that you have to go there more than once and the Claydols will still be there.
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112* A [[UnlicensedGame SNES bootleg]] called ''VideoGame/PocketMonster'' (also titled "[[SpellMyNameWithAnS Picachu]]" in the box art) has the third stage, named "Jump Around". [[PortingDisaster Due to the bad programming compared to the Sega Genesis port]], it became UnintentionallyUnwinnable. It is composed of an [[BottomlessPits enormous hole]] that fills almost the entire stage and Pikachu needs to [[JustifiedTitle jump around]] small lifts to complete the stage (whose graphics and level sprites [[NewWorkRecycledGraphics were almost entirely ripped]] from a stage of the Genesis game ''VideoGame/{{Quackshot}}''). The problem? Many of those lifts sometimes simply disappear from the stage due to the bad framerate of the sprites and the limitations of the console.
113* ''Empoleon's Snow Slide'' in ''VideoGame/PokeParkWii'', especially when you're trying to get all the bonuses by beating the required time limits. Your worst enemy isn't another Pokémon, but rather the ''wall''. That's right, walls are your worst enemy in this minigame. They slow you down, you will ''always'' hit them when you make a turn (Yes, even if you slow yourself down deliberately beforehand), and they are ''everywhere''. It's especially bad when you're using a particularly fast Pokémon such as Empoleon or Glaceon, who seem to be magnetically attracted to hit every single wall in existence.
114** The "Obstacle Hop" skill game in which you befriend Machamp. Remember how easy the first one was with Spearow? Well, welcome to Pokémon's version of PlatformHell. Complete with bad camera angles, surprisingly difficult jumps, and Machamp hurling boulders at you that are ''impossible'' to dodge.
115** The ''Lava Zone'' has one notorious side-quest that's both frustrating and difficult. Long story short, you have to bring some iron ore (that you get via drill) down to where Camerupt is so that you can use it to make a new lever for the furnace (the old one broke). However, not only do you have to deal with the shoddy camera angles in the game (causing you to get stuck in areas that you think you can walk on), but you also have to deal with Torkoal. A lot of Torkoal. [[RuleOfThree A]] '''[[RuleOfThree lot]]''' [[RuleOfThree of]] '''[[OhCrap very angry Torkoal]]''' that will constantly ram into you causing you to drop the iron you need to fix the furnace and advance in the game. Did we mention that ''any'' time you carry an item, you move at about one-fourth of your normal speed, you can't dash, and you are unable to use Thunderbolt? [[SarcasmMode Good luck getting past all those angry Torkoal]]. Oh, and did we mention that the Torkoal will chase you all the way to where Camerupt is and will still ram into you afterwards?
116** Granite Zone has a particularly annoying area where you have to step on a switch and jump across timed platforms in order to progress in the game. The problem lies in the game's poor camera angle and controls. You cannot just dash across, or you'll fall, and you have to move quickly while jumping or else the platforms will disappear. In other words, [[SarcasmMode have fun doing the same part over and over again]].
117* In ''[[VideoGame/PokemonStadium Pokémon Battle Revolution]]'', Sunset Colosseum. During the actual game, it's a rental matchup, with you and your opponent choosing four Pokémon from a pool of 12. It's hard to predict your opponent's choices and you may not always have the moves to beat them. The Colosseum boss usually uses Vigoroth, with Body Slam and Brick Break, and Gible with Dragon Rush. Then there's his Grovyle with Leaf Blade. And if you choose Gible, look out for Luxio with Ice Fang. Then, once you beat the game, this level turns into a several set survival challenge without a guarantee of healing at the end like usual. You spin a wheel that tells you if you'll get PP restored, HP restored, items restored, etc.
118** If you thought you would sweep the game by bringing a team of ridiculously powerful Pokémon...welcome to Neon Colosseum. The Pokémon are randomly chosen from both your team and your opponent's team...which means, more often than not, you will end up with your opponent's crappy Pokémon and your opponent will get your OlympusMons. Good luck.
119* The higher ranks of the Colosseum games, (Rank 8, Level 50), where everyone uses [[OlympusMons Legendaries.]]
120* ''Pokédex 3D Pro'' has various daily quizzes, and they range from simple (name the given Pokémon from, say, the Johto region) to tough (name the given Pokémon's Egg Group). But if you happen to find one about learnable moves, prepare to tear your hair out. There are many questions, and they are incredibly difficult. Some make sense (Arcanine can't learn Water Gun, silly), some are a given (Double Team, Protect, Rest, Toxic, etc. can be learned by nearly everyone) some require more thinking (that blade-slinging Pokémon could probably learn False Swipe or Slash...), but some just don't make sense at first. Normal-types are major offenders. And then there's tutor moves, [=TMs=], and of course, Egg Moves. The quiz also loves to throw you off (which move can this Pokémon '''''not''''' learn?). It's a long, frustrating, luck-based mess, especially for the perfectionists.
121** Really want to get frustrated? A multiple choice quiz to name a Pokémon solely on its cry. And you have to complete it with no mistakes as fast as humanly possible if you want that gold trophy.
122** One quiz requires you to name Unown by their appearance. Sounds pretty easy, right? They're only the letters of the English alphabet, after all. Too bad the time limit for one particular quiz is ''insanely short.'' It doesn't help that some of the Unown aren't exactly clear, either.
123** One type of Daily Challenge can pit you against ''the entire Pokédex.'' That's right, you have to endure '''''649''''' questions in a row without making any errors. Just the normal "what Pokémon is this" quiz is brutal enough, but get something like Peek 2 (black screen with a tiny hole moving around that reveals the Pokémon) or Learnable Moves and you'd be better off skipping that day.
124* Togekiss's stage in ''Pokémon Shuffle'' is especially hard. It has a fairly limited number of moves and when it starts there will always be a specific pattern of panels made from Togepi, Togetic, and Togekiss which makes it look like one of the puzzle stages making you think there is a trick to beating it. But there isn't, you just have to be lucky and try to work around the Togepi pieces.
125** Blaziken's stage [=EX12=] is also really hard. Blaziken has a really small time limit to beat it of only 30 seconds, and Blaziken really spams disruptions. You have to be lucky with combos and even then you will probably beat it with very little time to spare making catching it even harder.
126** Mega Gengar's stage is sheer madness and is very likely the first pay wall the player will hit unless he or she has jewels/a Complexity -1 on hand. Its board starts off absolutely littered with Eevee (which, thankfully, at least do some damage to it in this version, but still aren't effective at all), which makes starting combos almost impossible due to there being 5 different Pokémon (6 if you don't bring Haunter with you) on the board, but after 3 turns, it gets worse, with it sealing off movement between the middle 2 rows. Mega Gengar can potentially make super effective matches against itself with Haunters, but its health pool is so ungodly massive that they're practically moot.
127** Really, most Mega stages are notorious for being nerve-rackingly frustrating and requiring either an optimized team setup or Item abuse.
128** Milotic is known for being one of the worst non-Mega stages in the game. The entire board starts off frozen except for four squares in the middle (a MythologyGag to ''VideoGame/PokemonRubyAndSapphire''). This makes it infuriatingly hard to get any matches off without good RNG, and on top of that, Feebas is [[TheLoad a forced party member]], which can make it even less likely that you'll get any combos at all. Your best bet is to [[ViolationOfCommonSense also bring Feebas]], but even then, good luck S Ranking without Complexity -1.
129* ''VideoGame/PokemonRumble World'' has the challenge called "Restaurant Opening." In it, you must protect your Mii from wild Pokémon attacks. However, this EscortMission has a difficult twist; combine the fact that it has 400+ power, the fact that you are timed, the fact that every single Pokémon wants you dead, and the fact that if your Mii runs out of HP you automatically lose and you get a hard challenge that makes sure you have '''any''' Pokémon close to 400 power. Also, you have to deal with multiple bosses in one go, and it is not helped that the Pokémon will ''gladly'' gang up on your Mii, and that the weapons ''also'' damage your Mii. Also, fighting [[ThatOneBoss Slurpuff]] does not make it any better. So, while you can, make sure you get a Scizor, because you are going to need it.
130** Any escort mission becomes this in Hard Mode, but special note goes out to "The Phantom Thief Appears", where you have to protect [[spoiler:Diancie]]. Waves of enemy Pokémon gang up on it, it doesn't move around nearly enough to dodge effectively, and it attacks quite sparingly. On Hard Mode, the enemy creatures can tear through its health surprisingly fast. The best way to deal with it is to have a wide ranged Fighting- or Fairy-type attack to hit multiple opponents at once and have a very overleveled Pokémon at your disposal. Heal Pulse is useful too, but runs the risk of helping the enemies as well.
131* The final level of ''VideoGame/PokemonXD'', Citadark Isle. [[https://www.youtube.com/watch?v=YCvgN0HibWw#t=28m41s The Speedster puts it best.]]
132* The Giratina post game battle level in ''VideoGame/PokemonLegendsArceus''. You first battle [[spoiler:Volo]] with a full team in the 60s. Not too bad by then. But then you face level 70 Giratina twice, once in Altered Forme and then Origin Form. All without healing. And Origin Form is stronger buff-wise than Altered Form.
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