The Pokémon games have always varied in difficulty, especially with the changes to the experience share to a shared experience item form an equipable individual item. The actual design of the trainers and battles within the game often has little impact on difficulty.
Instead, most battles are made harder through level increases. However, some battles spread throughout the franchise are made incredibly difficult due to their inherent design. The difficulty of some of these battles is so high that many Pokémon fans remember these battles with a mixture of awe and fear, especially a particularly threatening Miltank from Goldenrod City…
10 Brock
Back in the day with no access to the internet, it was very uncommon for players to actually know what moves Pokémon learned at each level on top of type advantages. Being the first Gym Leader also means that the Brock fight was probably being completed by new players who didn’t know the intricacies of type advantages.
Fighting Brock in Pokémon Yellow with a Pikachu and another small rodent from Route 1 is incredibly hard. Only a Nidorino with double-kick could reliably get players through this fight, and most people had no idea that was even an option.
9 Claire
Dragon-types were harder to deal with back in the old days before Fairy-types. In the Gen 2 games of Gold, Silver, & Crystal, with only a couple Ice-types and only two Dragon-type evolutionary lines, players fighting Claire would need Pokémon capable of dealing and withstanding SERIOUS damage. But generally powerful Dragon-types were never Claire’s issue.
Instead, it was Claire’s under the radar destroyer, Kingdra. Being a Water and Dragon-type, Kingdra’s only weakness was other Dragon-type moves. And with only Dratini and Horsea, players didn’t have many options. On top of this, it knows heavy-hitting moves and smokescreen, so good luck hitting the thing; for those who manage, good luck surviving Kingdra’s own crazy attacks.
8 Whitney
Anyone who played through Pokémon Crystal remembers a battle that brought a fury like no other down upon unsuspecting players within the third gym. That’s right, Whitney, the Normal-type Gym Leader. With a simple Clefairy and Miltank, Whitney brought players to their knees.
Clefairy’s Metronome could mean life or death all at the whims of fate. Miltank’s Rollout, stab damage Stomp, and Milk Drink mean that if trainers don’t take out this powerhouse quickly they can expect a thorough thrashing. To top it all off, this is still early enough in the game that players don’t have access to revives other than what they find en-route, so a one-shot Rollout could be devastating.
7 May/Brendan
In Pokémon Emerald, the player’s rival isn’t incredibly difficult, however, for players hoping to speedrun the game, their third battle can make or break a good time. For Emerald speedrunners, they need to get to this battle with a level 18 Marshtomp. Unfortunately, this means a double weakness to their Grass-type, Grovyle.
Further, they will need to use stat-boosting items to make sure Marshtomp will survive and win the fight, but the only opportunity to do this is while fighting their Wingull. What makes this so difficult is that Wingull knows Supersonic and Growl, both of which can make it impossible for Marshtomp to defeat the rivals Grovyle. Ultimately, it all comes down to luck and which moves Wingull decides to use.
6 Red
One of the hardest fights in any Pokémon game is the climactic battle at the end of Pokémon HeartGold and SoulSilver. Fighting Red is a surprising challenge that many players assume they’re ready for before spending the time to really research this intense challenge.
Red’s team is such a threat because of its insanely high level. With Pokémon between levels 80 and 90, trainers will need to grind (even after beating all of the Kanto gyms) before they’re ready to take on this difficult fight.
5 Cynthia
In most Pokémon games, the champion of the region is meant to be the game’s most difficult fight, with varying degrees of success. Well, Pokémon Platinum is one game that definitely got this right.
With a team not dedicated to any one type, and the most powerful Pokémon of this generation in Garchomp, Lucario, Spiritomb, and Togekiss, players really need to watch their backs. Additionally, Cynthia’s team is a very high level, with her Garchomp maxing out at level 78. Overall, her team is just really really good.
4 Ghetsis
Ghetsis’ party in Pokémon Black and White is one of the hardest team fights in the franchise. With a generally powerful team that uses real strategies, Ghetsis makes many players quiver. His Eelektross has no weaknesses, his Cofragigus effectively stalls, his Seismitoad can only be stopped by Grass-types, and his Bisharp can only be countered by a solid Fighting-type.
The real kickers are his Hydreigon and his Bouffalant. The latter has incredibly powerful attacks and needs to be stopped quickly before it wrecks an entire team, but Hydreigon is an absolute monster. With incredible speed and devastating type coverage, this evil dragon is sure to leave a bad taste in any player’s mouth.
3 Evice
The final boss of Pokémon Coliseum is one of the hardest fights in the franchise’s history. With a 10 level jump from the fight that immediately precedes this boss battle, Evice is one bad man. Additionally, his team absolutely slaps.
With an Intimidate Salamence, a nearly indestructible Scizor, a Machamp with Rockslide and Earthquake, and a Slaking and Slowking that make an absolutely deadly combo with Skill Swap allowing the beefy sloth to attack every turn, Evice makes many trainers cry. Further, with an incredibly limited selection of Pokemon throughout the game, this battle is extremely tough.
2 Ardos & Eldes
These bad blue and red brothers from Pokémon XD: Gale of Darkness are two of the hardest fights in the franchise’s history. Because they’re about the same though, they can just be lumped together.
What makes them so difficult is how Shadow Pokémon work in this game. With improved Shadow-type moves that are super effective against all non-Shadow-types and teams with 4 Shadow Pokémon each, they really just make battles into a living hell. And worst of all, players are expected to catch their shadow Pokémon, meaning they need to stall through super powerful attacks hoping they can survive just long enough to put all of them away. Oh… but it gets worse…
1 Greevil
The final boss battle in Pokémon XD: Gale of Darkness is even harder than the two brothers before. With 6 Shadow Pokémon that bring massive super effective damage against all non-Shadow-types, trainers need to sustain a team for a long time.
Even worse is how trainers have to catch each of them before they can move on to the next Pokémon. On top of that, three of the Shadow Pokémon are the legendary birds, Articuno, Zapdos, and Moltres. With very low catch rates and devastating shadow moves of their own, these three leave any trainer questioning why they really need to catch-em-all.
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