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Hardest main-series Pokemon game (as of the end of Gen VII)

Jabberwocky

Gather round, people, I'll tell you a story
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Platinum can kick your teeth in if you're not careful. I struggled a bit with Ultra Moon, but that's mostly because I never did any grinding the entire game.
 

Rocket Zigzagoon

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BW because you can only battle in the stadiums at specific times of the day.
Also, Team Plasma Boss Ghetsis can give you even more trouble. The BW2 battle against Ghetsis is still easier than his last battle in BW1 (except if you use Challenge Mode in Key System, then he's still give you the same challenge).
 

Camille

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Platinum, easily. Cynthia's team is very diverse with good movesets, and Gardenia, Crasher Wake, Fantina and Cyrus aren't pushovers, either. The difficulty is one of the reasons I like Platinum so much, though.
 

Diamond & Pearl

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Sapphire was challenging for similar reasons. It took me a month to find Team Aqua's hideout underwater (which I found by accident) simply because my English level was not yet good enough to understand everything.
Ah, the memories... The things that took me months due to not knowing English at the time:

- Gen I (Red): Leaving Cerulean City. / Serving the police guard beverages. / Reaching Cinnabar Island.

- Gen II (Crystal): Leaving Violet City (Togepi you twat…). / Receiving the Squirtbottle that FINALLY enabled me to get that useless tree out of the way (the way it shaked never got old, though). / Receiving HM03. / Healing The Lighthouse's Ampharos. / Reaching route 44 (LET ME PASS BY AND STOP SELLING ME YOUR COUNTERFEIT RANGECANDYBARS YOU STUPID OLD BIN!!!). / Disturbing Snorlax's sleep (Curse you last remaining Rocket member whose English wasn't much better than mine back then).

- Gen III (Emerald): The disappearance of those Wailmers in Lilycove City. / Discovering Team Magma's hideout in Jagged Pass. / Finding Team Aqua's hideout. / Asking Rayquaza to solve Hoenn's weather problem.

By the time Gen IV was released, my English was sufficient enough. Maybe I'll start a thread about this subject.
 

prog rocker

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- Gen II (Crystal): Leaving Violet City (Togepi you twat…). / Receiving the Squirtbottle that FINALLY enabled me to get that useless tree out of the way (the way it shaked never got old, though). / Receiving HM03. / Healing The Lighthouse's Ampharos. / Reaching route 44 (LET ME PASS BY AND STOP SELLING ME YOUR COUNTERFEIT RANGECANDYBARS YOU STUPID OLD BIN!!!). / Disturbing Snorlax's sleep (Curse you last remaining Rocket member whose English wasn't much better than mine back then).
Happened to me, too, although it was because my parents got me a bootleg Silver copy so I couldn't advance after beating Whitney. Also, it had a weird trainer in the Goldenrod Underground that had this team: Nidoran♀ Lv28, Nidoran♂ Lv28, Nidorina Lv30, Nidoking Lv32. Seriously, how I was supposed to beat that at that point in the game?
 

CynthiaLover

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Platinum and BW, but that was one of the reasons why I liked those three games. They actually offered a challenge.

For Platinum, not only was the AI very smart, even regular trainers would use pretty much any move available to whatever Mon they were using, be it natural, TM, or Tutor, and they WILL capitalize on your weaknesses. The Gym Leaders and (of course) Cynthia were some of the more challenging ones, both being very smart and well-balanced.

As for BW, the fact that you had to start from scratch was a huge boon to me, as many of the not-so-golden oldies were getting annoying, as well as having a smart AI. And that created a challenge worth playing. Is it any wonder it took me so long to complete the games, as I was so busy exploring, experimenting, and figuring out new battle tactics that it took a while. And I loved that. Plus you really had to think smart when it came to grinding, as even the biggest pinata Mon, Audino, could be a decent threat if underestimated.

It's the reason why B2W2 aren't as fun to me as BW, as they were much easier, as well as bringing back a lot of old Mons, which tarnished the whole "fresh" feel of Gen V. Sure, there were a lot of higher incentives in the second half of Gen V, such as Move Tutors, Join Avenue, PWT, and so on, but it was quite a bit easier as a result, which was bit of a downer to me.

But, yeah, Platinum and BW are very high regarded to me because of the challenge they imposed, along with plenty of other good stuff thrown in. I really miss those days, as they offered a lot in their heyday. Nowadays, the AI is either on easy mode or just plain stupid, and there really isn't much of a challenge anymore. While I will admit that the Totems in USUM were a well-needed upgrade from SM in terms of tactics and setup, but they're still a bit on the low side compared to how Platinum and BW could really crank out the challenge levels, which made winning all the sweeter in those games. So, in short, Platinum and BW were very much golden games because of their challenge levels and the fact you had to really think smart with them.
 

Jammy2A

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Platinum (Damn you Cynthia! Damn you Garchomp!)
G/S (I was very young, which played a role)
B/W (I admit the elite four took me by surprise the first time around)

Beyond that Ive never felt much of a challenge, unless Im making it explicitly difficult: being under-levelled, running a mono-type team, insisting on not using any recovery move/item, etc.

In fairness, I see a lot of people say USUM is hard, but I never did get around to finishing it, so maybe I should give it a proper go. Reading everyone's story about how tough it is makes me want to see it for myself :) Especially after how..... "light" SM was.
 

Kyriaki

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Platinum was the most difficult for me.
 

Aulos

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When I think of "difficulty" in Pokemon, I think back to the first two generations and how they were difficult just from how mechanisms were not fine tuned like they are in later Pokemon games. Things like wrap/bind preventing your Pokemon from being able to attack for multiple turns. Granted, that does make sense, but I hated those moves so much back in Generation I. lol. Confusion and Paralysis also seemed to feel a lot more rigged to hinder me than the opponent in earlier games. Certainly that still feels that way, but it just felt worse back in the early days. It's probably just my mind over-exaggerating.

Sun also felt difficult to me. Or moreover, as I've probably said multiple times, it felt like its difficulty was all over the place. You'd go into a Totem battle and the AI would be top notch, but then you'd fight your rival and they didn't understand the most basic of type matchups and repeatedly used moves like "Growl". However, I also found how weak all of my Pokemon felt to be frustrating. Moves like Surf one-shotted a lot more Pokemon pre-Gen VII than it does now and I don't like that.
 

Poké Boss

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For me it's Platinum, because Cynthia is a really strong battle.

But in terms of regular trainers, the hardest is BW2. After becoming Champion, some very tough, high level trainers appear.
 
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