10. Brock
It’s a bit strange to say that Brock is one of the toughest gym leaders since he had his very first gym fight in the early Pokemon games. But depending on what kind of starter you choose, these rock/ground types can absolutely crush you.
Good luck to all owners of the original Charmander in Red and Blue as this Pokemon doesn’t budge Brock’s Geodude, Onix, and the Five Full Heals. You can pick up a Caterpillar or Nidoran and grind to level up high enough to beat the challenge, but that will take forever against the lower level Pokemon that exist before their Pewter City Gym.
A much easier solution here is to choose Squirtle or Bulbasaur in the original games. To those who stuck to it and persevered, I salute you and soon-to-be Schreuzard for your bravery.
9. Falconer
Falkner is another gym leader from whom you shouldn’t expect any challenge, as he is the leader of the first gym in Gold, Silver and Crystal. However, the hard part about his team is that he’s a flying type, which doesn’t offer any advantages to beginners, which is a bad match for Chikorita.
Things get even more complicated when you realize that both Pidgey and Pidgeotto know Mud-Slap – a floor-type move so effective against Cyndaquil and Onix that you can have it before the gym.
This move also reduces accuracy, so this fight is likely to be more challenging than any right to have a confrontation that occurs early on.
8. Wallace
Wallace is the leader of the Aquatic-type gym in games completely filled with Aqua-type Pokémon. He also has a certain Pokemon that completely negates Grass and Electric type weaknesses. He comes late in the game, but he’s ready for you.
Even if you have a Grass-type to battle with, both Milotic and Sealeo know the Ice-type moves to respond to, so it’s best not to mess around. Milotic’s Ice Beam and Whiscash’s Earthquake, in particular, are unmissable.
To top things off, each of Wallace’s five Pokémon knows the Water Pulse, which has a chance of getting jammed if hit.
7. Elisa
Elesa is the fourth gym leader in Pokemon Black and White, and her settings are downright noisy. Two Emolgas along with Zebstrika can cause a lot of problems for those who think they can only go in with Earth types to win.
All three starters will be at a disadvantage when facing Emolga at this point in the game, so it’s up to the rest of the other Pokemon to beat one of Gen V’s most problematic gym leaders. Unfortunately, Emolga is only weak for rock and ice moves.
As if the genre flaws here aren’t enough, two Emolgas have the static ability, which can cripple your physical attackers. And each of its three Pokémon know Quick Attack and Volt Switch, which makes this game a game of electric hide-and-seek at times.
6. Winona
Winona’s Flying-type Gym comes right after another tough fight against Norman at Ruby and Sapphire, and has something to take on all of third-generation beginners. Treecko and Torchic’s evolution streaks are weak for Pokemon Winona, and the Mudkip streak can’t use any Water or Ground type attacks that might be useful here.
Biliber covers her rock-type weakness while Skarmory and Altaria deny the electric type’s weakness. Rock and Ice moves are your best bets here, but even that can be dangerous if it’s really coming from a Rock and Ice-Type Pokemon.
Even if you have all the right scripts for a fight, Winona’s Altaria is a problem. Its movement combination of Dragon Dance, Earthquake, Aerial Ace, and Dragon Breath can easily make a few holes in an unprepared team. Let her down enough Dragon Dances, and she’ll say goodbye to a few party members when the earthquakes start to appear.
5. Norman
In Ruby and Sapphire, Norman will totally bully you with two Slakings and a Vigoroth. These sloth/monkey hybrids will sit there while you do your best to reduce their health. While they take these hits, one will recover using Slack Off, the other will put you to sleep with Yawn, and both can force you to use moves you don’t want with Encore.
Slakings have a lot of high health and defenses, so poison might be a good idea, right? Well maybe. They, along with Vigoroth, also have a movement interface, which enhances the attack when the Pokemon is under the conditions of a certain state.
Depending on your party setup, you’ll be in this for the long haul. Of course, this fight is a little easier with Combusken or Blaziken, but even with the genre advantage, Norman also has two potions of Hyper to use whenever he feels like it. Norman is the latest Hoenn Gym leader on this list, but this Pokemon Generation really got you working for your badges.
4. Claire
Before she started cheating with Gyarados in HeartGold and SoulSilver, Claire defended the Dragon gym with a team of three Dragonairs and Kingdra in Gold, Silver, and Crystal.
There aren’t a lot of options for battling this team in the second generation, but luckily it gives you Pryce Ice-type TM before you have to take Clair head-on. He will certainly help her with the Dragonairs, but the Water/Dragon-type Kingdra will easily get rid of her.
This fight really makes you realize that the fairy type was a godsend because Kingdra was only weak for Dragon type moves at the time, and every Pokémon in Clair’s team could use Dragon Breath to take on any dragon you brought in while also crippling the rest of your team. All Dragons know Thunder Wave for more crippling potential, and one even knows Ice Beam, just for good measure.
3. Whitney
We probably all knew Whitney would eventually be mentioned on this list. Some of us still have nightmares about Miltank, but that’s okay – we’ve hit Gen VIII and she can’t hurt us anymore.
But, man, I blocked most of the teams in the second generation. Miltank could be a real hit (or multiple times) and make Whitney one of the toughest gym leaders in Pokemon. Encore Clefairy’s Encore is more annoying than worrying, but its Miltank can neutralize a male Pokémon with Attract, heal itself with Milk Drink, and end life with Rollout.
Whitney’s Gym is third in Gold, Silver, and Crystal, and very few Pokemon you can catch up to that point can actually do real damage to their team. This is another battle that – like Norman – forces you to attack with anything and everything. Most of the time, you’ll just wish your HP Miltank reached zero in the end.
2. Blue
Blue is another cheater who breaks with tradition, but are we really that surprised? There is no real specific type of gym for him. Instead, he uses Blue Pidgeot, Alakazam, Gyarados, Exeggutor, Arcanine, and Rhydon to take you.
This is a challenge for several reasons – the first and most obvious is the need for a diverse and balanced team to overcome it. Almost all of his Pokémon are at level 60 and most of them have movement combos that are difficult to work with in the second generation.
Look at the team and you’ll see what I mean: Alakazam has Disable and Recover, Rhydon has Sandstorm and Earthquake, Gyarados has Hydro Pump and Hyper Beam, the list goes on. This is more like a hero fight than a gym fight, and Blue lets you see why he turned into a champ at some point.
1. Sabrina
Sabrina presents the toughest fight of all the gym leaders due to how broken Psyche-type Pokémon were in the first generation. Their only weakness was the Bug type because Dark didn’t exist yet and Ghost wasn’t very effective. Her team consists of Kadabra, Alakazam, Mr. Mime and Venomoth are just for some toxic fun.
To make matters worse, the only moves that deal damage in the first generation were Pin Missile, Leech Life, and Twineedle – all of which did secondary damage. Those were your super effective options against Kadabra and Alakazam that could use Recover, and Mr. Mime with bulkhead and light screen, and Venomoth who can use Poison Powder and Stun Spore for fun.
This fight is tough for all the reasons mentioned above, plus Sabrina has an overdose that she may or may not use to make the fight more difficult.
There are a lot of gym leaders in the Pokémon franchise, so we may have missed some other challenging battles. Let us know which ones caused you the biggest problem in the comments section below.
Featured Image Source: OLM (Pokemon Generations)