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Trying to catch 'em all? Then prepare to Skull Bash your head against these stumbling blocks along the way.


Mainline Games

  • Pokémon Red and Blue:
    • Brock goes from being a Warm-Up Boss in the original games to this trope in Pokémon Yellow, as your starter Pikachu is completely worthless against him despite the lower levels of Brock's team, and no, you can't cheat the type system as they do in the anime or manga. To compensate for this, the player can catch a Mankey (Fighting) early on in Route 22, which can deal super effective damage against Rock types, and the Nidoran from the same area now learn Double Kick (a Fighting attack) at level 12 rather than level 43 — teaching the player to catch and train other Pokémon to cover for the weaknesses of their starter.
    • While Brock is easy to overcome with a bit of game knowledge and/or some grinding, Misty definitely serves as the wake-up call for those who chose Charmander or are playing the Yellow version. Her Starmie is a competitive tier Pokemon with its high speed and special attack, and it can soak multiple super-effective Thundershocks while sweeping your entire team with Bubblebeam, which is the strongest move at this point in the game at 65 Base Power. For Red/Blue players who chose Charmander, Oddish and Bellsprout are the only Pokemon at this point of the game who resist water and can outlast Starmie and even so, they require a bit of grinding before they can be effective counters to it. Yellow players could instead obtain a free Bulbasaur from an NPC. Either way, challenging Misty without leveling up that grass type solely for this purpose makes winning the battle dependent on the A.I. Roulette and if she misses attacks. Even if you have one of the above Grass-types, due to how high Starmie's special is and how all three, even when evolved at least once, have pretty low-power super-effective moves, you're still likely going to struggle against Starmie. Just a little bit less than with any other option. Surprisingly, the arguably best option against her is the Magikarp you can buy at Mt. Moonnote .
    • Lt. Surge is easy in Red and Blue, but acts as a nice reminder you can't always rely on super effective Pokemon to carry you through Yellow. His Raichu's high Speed will easily allow it to Mega Kick your Rock/Ground Pokemon before you can even react, so you must instead must rely on attrition wearing the enemy Pokemon down.
  • Pokémon Gold and Silver:
    • Gold/Silver had Falkner. Up until this point, you've probably curbstomped every trainer you've fought. Your Rival? The Sprout Tower? Those are easy. If you picked Chikorita as your starter, it's got a natural disadvantage against his Flying-types. Picked Totodile, nobody has an advantage. Picked Cyndaquil, or you think you did you homework and decided to use Geodude/Onix/Mareep to sweep the competition? Mud Slap will not only hit hard at this point in the game, but will screw your accuracy. And Falkner's Pokemon are most likely faster than your "good options", so you're going to struggle actually making your super-effective attacks land on his Pokemon.
    • Whitney. Oh sweet Arceus, Whitney. To say that she exemplifies this trope in the franchise would be selling it short: while her Clefairy is nothing to be afraid of, it's her Miltank what can veritably drive you insane with its combination of high stats for early game and absurdly annoying moveset. First off, it knows Attract, which inflicts a status ailment similar to paralysis but only works on 'mons of the opposite gender: if your current Pokemon on the field is male, it's lights out. It also knows Rollout - a move that inflicts doubling damage over five turns, Stomp - which has a high chance of making your Pokemon flinch and from which it gets STAB, and Milk Drink - which allows it to restore half of its health. It only gets worse in HG/SS, though, as it gains the Scrappy ability which lets it hit Ghost-types and also holds a Lum Berry to cure it from status ailments. However, there's an Easy Level Trick for this battle: if you managed to catch a Drowzee earlier on you can trade it with an NPC in the Goldenrod Department Store for a female Machop which resists Attract and Rollout and can hit for super-effective STAB damage. Knocking down her Miltank will still take some time but it'll certainly be far less of a headache. Another fairly easy level trick would be to exploit Rollout's limitations and either use Dig/Fly to kill Rollout's momentum, or spam an accuracy-lowering move like Sand Attack or Mud Slap, which has a chance to kill Rollout's momentum and will also make it harder for Miltank's other attacks to land on you.
    • Falkner serves this role again, but in a different way, in HeartGold and SoulSilver. This time, he serves as an alarm clock for veterans re-playing the game who expect everything to be the same. Up until Falkner, there have been a few changes from the originals, but when you reach him and realize his Pidgeotto took a level hike — from 9 to 13 — and then watch Pidgeotto heal itself using Roost note , you realize the game is broadcasting a big hint with the subtlety of a megaphone: "Boss fights in this game aren't going to be retreads of the original."
  • Pokémon Ruby and Sapphire:
    • Roxanne, the very first Gym Leader, can be tough especially if you don't have an evolved starter, or didn't choose Mudkip. Her Nosepass is very bulky for this point of the game and even a Treecko with Absorb can take more than a few turns to knock it out. It also has Rock Tomb which will mire your mons' speed and actually hits pretty hard. If you've chosen Torchic you'll either need to grind and evolve it or be very creative to win without suffering a lot.
    • Flannery, despite her nervous demeanor, can be a challenge due to being the first Gym Leader in the Hoenn games that actually tries to employ something resembling a long-term strategy, thanks to her Pokémon having a good number of support moves — many of which they can't learn naturally, only by TM, which could throw off some players. Her two Slugmas come with Sunny Day, which empowers fire-type moves (and lowers the power of Water-type moves, which are what most players would typically resort to against a Fire-type specialist), and Light Screen, in order to raise their team's special defense and resist such attacks even more. One of them also has access to Smog, a Poison-type move which balances out its low power with a high chance of poisoning the target. It's clear that the two Slugma serve to weaken your team so they become easy pickings for her signature Torkoal. The fire tortoise naturally has high defense, but if the Slugma managed to pull off some setup before you knocked them off, you'll be dealing with increased special defense from Light Screen and a devastating Overheat that has been made even stronger by Sunny Day. Oh, and it has the White Smoke ability, so don't even try decreasing its stats. Even if your Pokemon are able to resist fire attacks, they can still end up infatuated or paralyzed to death, as Torkoal knows both Attract and Body Slam. Emerald makes things even worse, as her entire team now runs Sunny Day, and she also has a new team member in a Camerupt that's a good 7-8 levels below its evolving range and is as strong as her Torkoal. While she's still manageable due to her team being very slow and susceptible to water, if you end up struggling a lot against her, then chances are that you're not ready for Norman, as Flannery serves as a sort of preview for Gym Leader nastiness from that point on.
  • Pokémon Diamond and Pearl:
    • Roark and his Cranidos. Cranidos has an attack stat of 125 at the cost of piddling defences, but it also has Headbutt (attack of 70) which is perfectly capable of tearing through any first stage starter in two uses if you are lucky. It also has Pursuit which means it can attack as you switch out and Leer to lower your defences and make Headbutt hit even harder. In addition, the fact it's an offensive Pokémon can throw off veterans who were accustomed to Brock and Roxanne using more stereotypically defensive Rock-types, especially because Roark starts off using Geodude as usual.
    • Mars is surprisingly brutal for such an early boss when fought the first time, for one reason: her ridiculously underleveled Purugly note . It's very fast, packs a surprisingly strong Scratch and Faint Attack, will take multiple hits to defeat due to its high level, and can use Fake Out to get a cheap shot in on your Pokémon when it's sent out. Even Monferno may struggle to win unless it's overlevelled, despite its type advantage — teaching the lesson that type advantages aren't everything, and having your Pokémon at a high level is also important.
  • Pokémon Black and White have Lenora, the second Gym Leader and a specialist in Normal-type Pokémon. Her Pokémon's levels are a decent jump from the previous Gym Leaders and both have pretty strong attacks for how early in the game she's fought. Her Watchog also has Hypnosis to put one of your Pokémon to Sleep, which will likely shut them down for a few turns, and she can use Retaliate after one of her Pokémon falls to take out your current Pokémon and put you on the defensive. A bit later in the game, there's also Elesa, who teaches you that you can't always rely on type matchups to win battles for you — she may be an Electric-type specialist, but she packs two of the Electric/Flying Emolga, who will happily evade your Ground-type attacks while hitting back with Aerial Ace.
  • Downplayed in Pokémon X and Y, due to the lowered difficulty, but the first two gym leaders are a lot more savvy with their movepools, so the trope still applies:
    • Viola is a Bug-type specialist, so you can easily blaze through her team with a Fennekin or by catching a Pansear in Santalune Forest or Litleo on Route 22, right? Not so fast. Viola's first Pokemon is a Surskit, a Water/Bug-type that is neutral to fire attacks, will use Water Sport to make your fire attacks even weaker, and then will wash them away with Bubble. (And if it's not doing that, it's getting the jump on you with Quick Attack.) note  At least if you can get past Surskit, all you have to deal with is a Vivillon... that is likely faster than anyone on your team, mind you. (Interestingly enough, one of the best Pokemon to catch for this battle is Pikachu, as both Surskit and Vivillon are weak to Electric. Or, ironically, Chespin, which learns Rollout by that point.)
    • Grant is a Rock-type specialist, so you'd think it's a simple matter of exploiting his numerous weaknesses, yes? Well, not quite. His first Pokemon, Amaura is part Ice, with the Refrigerate Ability running off Take Down that effectively becomes a STAB-boosted Ice-type move comparable in power to Leonora's Retaliate. Then, his second Pokemon, Tyrunt is part-Dragon, which neutralizes Grass and Water-types' offensive advantages, and which is not a type you'd expect to see this early considering their general latecomer status in previous generations. It's Bite in particular thanks to the Strong Jaw Ability, and it's high attack power in general are also nothing to sniff at. He and Viola aren't as difficult as the rest per se, thanks to easier level grinding and greater Pokemon variety available, but this is partly made up by their curveballs strategies than can catch you out.
  • Pokémon Sun and Moon: The second Totem Pokémon, Totem Wishiwashi. Totem Gumshoos / Alolan Raticate only use the S.O.S system to get in a second attack, but Totem Wishiwashi uses two very clever double battle strategies. First, both of the Pokémon it summons know Helping Hand to give its already powerful attacks an extra boost. The other thing it will do is summon an Alomomola that knows Heal Pulse. Wishiwashi's ability depends on having high HP to send it into school form; if it gets down to 25% then it enters the weak solo form and Heal Pulse can counter that weakness brilliantly.
  • Pokémon Ultra Sun and Ultra Moon: Several of the totems have changed since Sun/Moon, and none of them are jokes. The first one to be changed is Totem Wishiwashi, having Totem Araquanid in its place. Wishiwashi and its cohorts rely mainly on using the rain to make their Water Guns strong enough to power through foes. Water Gun is all they have for offense- something like Paras, with abilities that nullify any Water attacks, shuts Wishiwashi down completely. Araquanid, however, is not so simple. It knows offensive moves of FOUR different types, something scary on its own when all of the bosses generally only had one or two offensive moves at this point. Aurora Beam, a strong Ice move at this point in the game, is able to counter any Flying types you may think to use, such as Dartrix or Hawlucha. Any other Grass types you may try to use will be destroyed by Leech Life, a powerful Super Effective Bug-type move that also restores Araquanid's health. Bite is probably its least useful move, but it will be used to defeat any Ghost types like Gastly you may try to use to inflict status on Araquanid. And finally, its strongest move- Bubble. While its base power is the same as Wishiwashi's Water Gun, Araquanid's ability effectively makes any Water move double in power. This ability, paired with the rain that always falls on this battle, will make even a neutral hit feel like a Super Effective one. Its allies are no joke either- Dewpider can do decent damage to you as well, and Masquerain can Paralyze you or boost Araquanid's speed. Even the best counters for this boss have trouble defeating it- this spider isn't a joke.
  • Pokémon Sword and Shield: Kabu, the third gym leader, is notable for actually declaring himself "the first real roadblock of the Gym Challenge" (though, perhaps ironically, he doesn't say this until after you beat him). The first two leaders are relatively trivial, having only one decent fighter, but Kabu starts with a Ninetales, followed by an Arcanine and a Centiskorch for the Dynamax-user. The first two persistently try to burn you with Will-O-Wisp, and the last has a Bug-type damaging attack that can catch you off-guard if you're attempting to breeze through with a Water or Rock type. Did we forget to mention that his Centiskorch can Gigantamax, thus giving it access to a move that automatically applies Fire Spin?
  • Lord Kleavor was a nice, easy introduction to fighting Noble Pokemon in Pokémon Legends: Arceus, but Lady Lilligant in the very next zone is a huge step up in difficulty. She's far more aggressive than Kleavor, constantly leaping around the arena and throwing attack after attack at you, all of which generate huge shockwaves that have to be dodge-rolled through. And while stunning Kleavor was as easy as getting him to dash into a wall, you have to consistently dodge Lilligant's massive arena-spanning shockwaves to tire her out. The boss battles against Noble Pokemon only get harder from here, and if you're struggling against Lilligant, you are not prepared for the likes of Arcanine and Electrode.
  • Pokémon Scarlet and Violet:
    • Katy, ostensibly the first Gym Leader you're supposed to challenge and the one easiest to find first, has three Pokémon of roughly equal levels (14, 14 and 15) while most prior first Gyms had one weak Lv 10-12 and a Lv 14 ace, and her "ace" is a Bug Tera Teddiursa that spams a boosted Fury Cutter, a move that gets stronger with every use. If you haven't leveled up or don't have an answer to Bug, she'll steamroll you.
    • Iono can easily become a stumbling block if you favor a defensive playstyle. Her first three Pokémon aren't too bad, though they do have a few tricks to cover their Ground-type weakness — Wattrel is Flying-type and so ignores Ground moves, while Bellibolt knows Water Gun to soak them. No, what pushes Iono into this trope is her ace, a Mismagius (Terastalized into an Electric-type) packing Hex and Charge Beam, the latter of which will likely boost its already great Special Attack when used. It also packs the all-dreaded Confuse Ray, which despite the nerf to confusion can still be plenty annoying since you have to gamble on your Pokémon hitting Mismagius or switch out, making you lose further momentum and potentially give Mismagius yet another window where to use Charge Beam. Finally, Mismagius has Levitate, negating damage done by Ground-type moves, which just so happens to be the only type Electric is weak to. If you leave Mismagius on the field too long, it'll boost its power and start steamrolling your team, with even Electric resists being likely to take huge damage after a while. This fight is designed to teach you that, against an Increasingly Lethal Enemy like Mismagius, it's best to go on the offensive and defeat it before it can pose a threat instead of trying to wear it down.
    • The first battle of The Indigo Disk DLC is a warm-up against Lacey, who sends out Plusle and Minun at first. Instead of having their weak Plus and Minus abilities, however, they have their Hidden Abilities, Lightning Rod and Volt Absorb, which they will exploit by spamming Discharge, which will both damage both your Pokémon as well as buff/heal their partner. And bringing a Ground-type isn't entirely safe as Plusle has Grass Knot as a coverage move. And if you take one of them down, the next Pokémon Lacey sends out is an Excadrill, which is immune to Discharge (meaning Lacey can keep spamming it), and is a very powerful Pokémon in its own right. All this serves to warn the player early on that the DLC battles will use competitive strategies, that relying on type advantages will not be able to carry you, and most importantly, if you go into this DLC without proper strategy, you will not have a good time.

Spinoffs

  • Pokémon Stadium:
    • In Stadium 1's Gym Leader Castle, Lt. Surge will probably hand new or more casual players their first loss. Up to this point, if they're using the Rentals, players have probably been filling their team with Pokémon strong against the gym's type and succeeding with it up to this point, so against the Vermillion Gym they naturally fill up their team with Ground types. Such players then get a rude awakening against Surge, where both his Raichu and Pikachu have Surf, outspeed all the Ground Rentals except for Dugtrio, and with said move will one-shot all the Ground Rentals besides the Nidos, leading to many players their first time through getting their mono-Ground team helplessly swept by Surge. Once you're aware of this and don't just try tackling Surge with a team of only slow Ground types he really isn't hard, but he shows you're very much going to have to deal with trainers covering their weaknesses and having access to good coverage moves from that point forward.
    • In Stadium 2's Johto Gym Leader Castle, Jasmine of the Olivine Gym serves as the wake-up call. While previous trainers and Gym Leaders switched Pokémon occasionally, Jasmine will constantly switch out her Pokémon to get the advantage on you, and her team is more varied compared to those of previous trainers and Gym Leaders. If you plan/react wrongly to Jasmine's switching, she will get the advantage and can defeat you. Though if you anticipate and react to her switching correctly, she can be pretty easy, especially if you exploit her team's weaknesses. Overall, Jasmine basically reminds you that your future opponents can and will switch their Pokémon on you to give themselves the advantage.
  • Pokémon Colosseum: Between the perpetual Double Battles, limited Pokémon to choose from, and trading being prohibited until the post-game, Orre is no joke, and at least one of the following three opponents is sure to be your tripping point.
    • Miror B. has a dance squad of no less than four Ludicolo, whose abilities benefit from rainy weather, which all of them can invoke with Rain Dance. Because of how Shadow Pokémon work, the only Pokémon you can level up at this point in the game are your starter Espeon and Umbreon, who can't get the type advantage; if you try to use your Shadow Pokémon, you're stuck with a level disadvantage. Two of the Ludicolo know Astonish, which might cause your Pokémon to flinch and lose the turn; one of them knows Leech Seed, which will stick the Pokémon it hits with an HP drain until its withdrawn and heals Miror's Pokémon to boot; three of them have Water-type attacks that will be bolstered by the rain, and all of them have a Grass-type attack to hit anything that resists Water. And once you take out three of the dancers, he sends out a Shadow Sudowoodo, who has a five-level advantage on his Ludicolo and shares none of their weaknesses.
    • Cipher Peon Skrub will tank with Clamperl and Wynaut (the latter of which will return fire like the Game-Breaker it is) while thrashing your team with Geodude's Magnitude and his Shadow Hitmontop. You can't rely on pure power to overcome Clamperl or Wynaut, because if you do, Geodude and Hitmontop will make you suffer. Hitmontop in particular is the first time in the game where an opponent's Shadow Pokemon can really wreck your team, forcing you to play strategically, especially if you plan on enduring attacks while trying to Snag it. And your Shadow Pokemon don't gain levels until you beat this guy.
    • Dakim. His Earthquake+Protect combo will decimate an unprepared team, and then the player realizes he has a Shadow Entei. This is a massive step up from anything the core series has in store - not only is this Legendary Pokémon participating in a Double Battle, but wild Pokémon - including wild Legendary Pokémon - don't use tactics at anywhere near the level of trainers. But Colosseum believes in Artificial Brilliance, and combining that with the stats of a Legendary Pokémon is already spelling disaster before you factor in Shadow Rush and its low catch rate.
  • There's the battle against Gurdurr and Scraggy in Pokémon Mystery Dungeon: Gates to Infinity. It's essentially the first major boss, but at this stage in the game, they can easily wipe you. They're both very strong, you've got only two team members, and if you're too reckless, you won't last long unless you keep healing up. There's also nothing you've got that's super-effective against any of the two, leaving you to chop away with regular-powered moves. If you chose Tepig or Pikachu as your character/partner, watch out; if Gurdurr gets burned or paralyzed as a side-effect of Ember or Thundershock, his Attack will skyrocket, and he'll easily destroy you in three, if not two hits. Plus, Scraggy has surprisingly high defenses. It's difficult enough that later on, when Gurdurr fights alone, it's much easier since it's a two-on-one battle. But still, this is enough to warn you of what's to come in this game's bosses.
  • The Pokémon Ranger series has several:
    • The original Ranger has two, both found in the Jungle Relic.
      • Salamence takes 22 loops to capture, far more than any previous boss, and has two powerful attacks: an earthquake that hits the entire screen, and a beam that comes out fast. To add insult to injury, it also No Sells your partner's Discharge assist and you can't bring any other Pokémon into the battle, teaching you that you can't always rely on your friend Pokémon to bail you out. Unless you're fast enough to quickly loop Salamence 22 times, being careful to avoid touching it or accidentally getting hit, you'll never win.
      • Flygon takes the opposite route from Salamence: it has just 6 loops, but flies across the screen at supersonic speeds while launching tornadoes. Unlike most previous bosses, you can't just wait for Flygon to stop attacking and quickly loop it; instead, you have to take the initiative. Like Salamence, it's also immune to Discharge and you don't get any other assists, making the battle a pure test of your reflexes and speed.
    • Shadows of Almia also has two:
      • Ramparados deals much more damage than any prior enemy, having three powerful attacks that can drain your Styler’s energy quickly. It also requires a bit more strategy to defeat, as trying to loop it without paying attention to what it’s doing is a recipe for disaster; you’ll have to wait for an opening before getting any damage in on it.
      • A bit later on, there's Drapion, which is another major difficulty spike. First off, you have to fight it directly after two Rhyhorn and three Stunky. Secondly, the only nearby Pokemon with an assist that's super effective against it at the time is Drowzee, which may or may not help. Third, it hits HARD. However, what really makes this fight difficult is that is has a nasty habit of leaving poison puddles, limiting the area you can circle it and latter starts spamming a poison cloud attack, limiting the time you can circle it. If you try to constantly loop Drapion without paying attention to the state of the battlefield or what it's doing, you'll have a hard time.

Fan Games and ROM Hacks

  • Drayano60 is known for his Nintendo Hard ROM hacks. So naturally expect these.
    • Renegade Platinum: Roark's Crandios is packing Zen Headbutt to deal with Fighting and Grass/Poison types, Thunder Punch to deal with Water Types, and Rock Tomb + Scary Face to make taking advantage of its low speed much more difficult.
    • Rising Ruby and Sinking Sapphire: Brawly's Makuhita got upgraded to a Hariyama. On top of that, it's got Smack Down to counter Flying-types, Bullet Punch to out-speed and deal massive damage to Fairies, and a Sitrus Berry to supplement its already massive bulk.
    • Sacred Gold and Storm Silver: Whitney is as tough as ever, but this time she's packing quite a few Fighting counters.
    • Blaze Black and Volt White: Cilan, Chili, and Cress are all packing full teams of the type they specialize in, but you don't get much in the way of ways to hit them for super effective damage outside of the Elemental Monkey that you get in vanilla. Also, you're facing them in a rotation battle, which adds an extra layer of strategy that you have to think about.
    • Blaze Black 2 Redux and Volt White 2 Redux: Roxie is packing the Toxic Spikes + Venoshock combo, and once her Koffing is done setting up Toxic Spikes it'll use Explosion to take out one of your Pokemon and force a switch-in.
  • Pokémon Inclement Emerald increases the difficulty even early on, despite the much wider selection of Pokémon, and Roxanne, originally a Warm-Up Boss, is there to drive that point home. Instead of her fairly weak Geodude, Roxanne is packing an entire team of hard-hitting and/or bulky Rock Pokémon to support her Nosepass — her Tyrunt and Anorith are particularly frightening attackers. Nosepass is still her ace, but it comes packing Fire Punch as a nasty surprise for any Grass-types on your team, and has Bulldoze and the newly-buffed Rock Tomb to drag down the speed of anything faster than it. Trying to fight her Pokémon head-on is a terrible idea; instead, you'll have to use some actual strategy by wearing them down with status moves and debuffs, like many later opponents. It's telling that an NPC outside the gym suggests that you level grind your starter until it evolves, just so you'll stand a chance.
  • Pokémon Infinite Fusion: The first battle against Giovanni in the Celadon Sewers makes for a surprisingly tough fight, as he's using two level 32 Pokémon and a level 35 one at a point in the game when most of the surrounding trainers have levels in the mid-to-upper 20s and the player's team is unlikely to have finished evolving yet. The big problem is his level 35 Haunter/Kangaskhan, which not only has a high likelihood of outleveling anything the player brought to the fight by a considerable margin, but is surprisingly fast, can effectively use both of its attacking stats, and has three immunities thanks to its Ghost/Normal typing. People who go into this battle unprepared often end up watching as Haunter/Kangaskhan shreds through their team without being able to land any hits on it. Even managing to defeat him doesn't provide any reprieve; the fight marks a sudden jump in the game's difficulty as the battles right after Giovanni (Celedon Gym and Pokémon Tower) are in the same level range as him.

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