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

JFrombaugh

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Just for clarification, by hardest I mean specifically beating the Elite Four & Champion. No post-game quests or any of those 3D Pokémon games like Stadium.

For me I'd have to say, in order of hardest to not-as-hardest:

1. HeartGold/SoulSilver
After all these years of playing Pokémon RPGs, I still find HGSS very hard, in particular because of how tough Falkner, the second Rival battle, Whitney, Morty, and Clair can be. The Elite Four are not a cakewalk either - many of them use status moves like Confuse Ray that will really test your patience and unless you spent hours playing Voltorb Flip for an Ice Beam TM, chances are you'll only have Ice Fang or Blizzard for Lance's Dragonites. And that also sums up a much bigger problem - your Pokémon selection for the main Johto part of the game is extremely limited due to the two-region nature of the games, and many of the best 'Mons for your in-game team are also well hidden, like Headbutting (specific) trees to get a Heracross, or catching a Lapras in Union Cave on a Friday.

2. Ultra Sun/Ultra Moon
After a super-easy Gen VI, GameFreak certainly did not shy away from challenging their fans this time around. The Totems are even tougher than before and require a lot of foresight and strategy to take down, especially Togedemaru & Marowak. And Ultra Necrozma's Photon Geyser will OHKO literally almost anything that doesn't resist it. Thankfully, the affection perks got me out a tight spot many times in my first playthrough (especially the Focus Band effect), and Hau is a total pushover compared to Ghetsis & Cynthia.

3. Platinum
If you didn't do much extra training, your Pokémon will only be about Level 48 by the time you reach the Pokémon League, and the Elite Four & Cynthia will be basically impossible. However the Gym Leaders aren't too bad for the most part if you know your type matchups and take the time to train beforehand, and there's more than enough Pokémon in the expanded Sinnoh Dex to build a solid & varied team to take Cynthia down.

Other than those three games, I've never really found Pokémon RPGs to be that hard all-in-all, but then again I am a long-time veteran of the series.
 
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RetroPokeFan

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Ultra Necrozma's Photon Geyser will OHKO literally almost anything that doesn't resist it.
Just two attempts was all but enough for me to finish off Necrozma. Got destroyed the first try and then immediately proceeded to knock the yellow thing out of it's little treehouse and into the sun by the second attempt with Incineroar in tow.
 

prog rocker

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USUM has been the hardest for me. Second would be SM and third BW and B2W2 in a tie.

The easiest one for me has been XY.
 

Rocket Zigzagoon

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USUM has been the hardest for me. Second would be SM and third BW and B2W2 in a tie.

The easiest one for me has been XY.
Same here, even though IMO, B2W2 is easier than first BW unless you set the difficulty levels to Challenge Mode.
 

Contrainer

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The Totems are even tougher than before and require a lot of foresight and strategy to take down, especially Togedemaru & Marowak.
Actually, Marowak is super easy if you chose Popplio.
 

Oricorio

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Judging by the ones I played, definitely Diamond. Granted, I was a little kid when I played it, but the E4 and Cynthia are plainly ridiculous, and it took me weeks to get through route 216!

The others in order from most difficult to least are SoulSilver (granted, I started with Chikorita), Moon, White, White 2, Alpha Sapphire, and Y as the easiest.
 

Tactician Karina

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SM/USM had some Totem Battles that gave me a challenge while DPPt had a slightly challenging Elite Four imo.
 

BigBadButterfree

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The Sinnoh games, for me. I know Cynthia had like perfect Pokemon (hax) and was difficult. I lost a nuzlocke to her in Platinum. Pearl want much of an issue for me, but I was a dumb child and transferred my old strong Pokemon from fire red and used them. I feel cheap and dirty admitting that lol.
 

colours

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SM/USUM both were a bit more on the difficult side for me. Totem Pokemon really added that refreshing extra challenge that I've craved for in Pokemon for so long!

Honorable mention goes to Cynthia from DPPt for obvious reasons.
 

KrisiChiki

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It's a bit hard for me to judge because when I was younger the games seemed more difficult to me simply because I didn't have the same amount of knowledge and perception I do now.

Gold was very hard for me because I didn't know English while playing it the first time, so I had no idea what each move did and my only distinction was "this deals damage and this doesn't". I also didn't know you could use potions to heal your Pokemon and thus I had to train my Pokemon until they out-leveled everyone.

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. That and my team was imbalanced. I can't remember how many times I got destroyed by Steven. :ROFLMAO: I remember Emerald was pretty challenging as well. I think Gym Leaders had their teams updated and you were up against two villain teams on top of it. Subsequent playthroughs were easier. FireRed was easy for me.

I honestly don't remember how hard Pearl was for me. Cynthia and Lucian were really hard to beat, but other than that I don't recall having a particularly difficult time in other areas. Heck, even with Sinnoh's region design, I had no problem navigating it apparently. Platinum was easy for me because I transferred old Pokemon to finish it. I'm not happy about that, but I wanted to finish it in time for Pokemon BW. During the Platinum-HGSS era I had lost interest in playing Pokemon, partially because my real life friends were losing interest and later I got busy with life. I only finished HeartGold after playing Y, so by then I had plenty of knowledge on moves and team building.

Pokemon Black more challenging than Pearl I think, but I don't remember having trouble with it, except that my Pokemon were under-leveled when I challenged the Pokemon League to chase after N so the battles were difficult. Ghetsis was a tough battle, but my memories are a bit mixed from the time I replayed the game so I don't remember my first playthrough very well.

Y was the easiest Pokemon game I've ever played. AlphaSapphire was more challenging, but I deliberately tried to keep myself under-leveled, and I actually did get some pretty challenging battles as a result. Archie nearly destroyed me, though it helped that half of my Pokemon were weak to his Mega Sharpedo (and this wasn't done on purpose!). Even the Pokemon League was challenging for me and Steven almost beat me... until we were both left with our Mategrosses. The choice to spam Giga Impact was disappointing. They should have let him keep Earthquake. :(

Moon and UltraMoon were surprisingly challenging thanks to the Totem Battles; some of them had very clever ally Pokemon. Mother Beast Lusamine was also extremely difficult for me, and the Pokemon League was very challenging. I only won the latter because Nebby (last Pokemon standing) managed to resist 2 hits from Kukui's Incineroar (including his Z-move) with 1HP which let me revive and heal my Wishiwashi. Admittedly, my team was about 10 levels below the Pokemon League when I went to challenge it.

UltraMoon was a little easier because I knew what to expect and I personally found Ultra Necrozma a disappointingly easy battle, but I guess that might have been due to my team set-up. I didn't know anything about Ultra Necrozma so that was just a coincidence. I kept my Pokemon under-leveled in both Moon and UltraMoon, but this time it was mostly not going out of my way to train as opposed to AlphaSapphire where I avoided training and even skipped some trainer battles.
 
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Twilight-Kun

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How are FRLG hard, besides Misty's gym battle and having to spend time raising Pokémon to get items from Oak's aides?
Mind-numbing tedium that discourages you from playing is its own challenge

Newer games have made going back to older ones harder because so many quality of life features are gone
 

IncineROAR

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Pokemon Yellow

Trying to take down two ground/rock type Pokemon with an electric mouse is eh.. not easy
 

Rockapheller

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I respectfully have to disagree with Ultra Sun/Ultra Moon games. Necrozma-incident is overrated. Sure, I failed at my first try but with different order of my team, it was no trouble at all defeating it. I also struggled only a little defeating Togedemaru but that was all. Compared to past series, especially anything before the 3DS era, Ultra Sun and Ultra Moon are still one of the easiest games just like the rest of 3DS Pokémon games in my humble opinion.

If I were to rate the hardest games, I would come up with two options, first of which being HeartGold and SoulSilver. This is pretty much the most repititively mentioned issue on the Internet, but due to the level curve. It is limited to train the Pokémon, and you have to spend crazy amount of time to be able to challenge Red in the end. Besides that, unless you have a solid Ice-type Pokémon or a good Pokémon that can somehow face Lance's Dragon-type Pokémon, you will have troubles winning the league.

The second option is Black and White Versions 2. However, I am kind of unsure whether to rate it really hard or not. In my first play back in 2012, I had struggled way too much defeating the Elite 4 and the Champion. They most of the time OHKO'd me. But I wasn't careful about Natures back in the day. Maybe I was just really unlucky to have my Pokémon with disadvantageous nature and EVs to begin with. My last gameplay from last year was relatively easier and I defeated the league at my first shot. But I designed my team completely depending on the league.
 

prog rocker

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I respectfully have to disagree with Ultra Sun/Ultra Moon games. Necrozma-incident is overrated. Sure, I failed at my first try but with different order of my team, it was no trouble at all defeating it. I also struggled only a little defeating Togedemaru but that was all. Compared to past series, especially anything before the 3DS era, Ultra Sun and Ultra Moon are still one of the easiest games just like the rest of 3DS Pokémon games in my humble opinion.

If I were to rate the hardest games, I would come up with two options, first of which being HeartGold and SoulSilver. This is pretty much the most repititively mentioned issue on the Internet, but due to the level curve. It is limited to train the Pokémon, and you have to spend crazy amount of time to be able to challenge Red in the end. Besides that, unless you have a solid Ice-type Pokémon or a good Pokémon that can somehow face Lance's Dragon-type Pokémon, you will have troubles winning the league.

The second option is Black and White Versions 2. However, I am kind of unsure whether to rate it really hard or not. In my first play back in 2012, I had struggled way too much defeating the Elite 4 and the Champion. They most of the time OHKO'd me. But I wasn't careful about Natures back in the day. Maybe I was just really unlucky to have my Pokémon with disadvantageous nature and EVs to begin with. My last gameplay from last year was relatively easier and I defeated the league at my first shot. But I designed my team completely depending on the league.
Although the Necrozma incident is part of the problem, believe me, Gen VII was where I had to more problems with the bosses than previous games. Hell, doing a one Pokémon challenge in USUM was pretty hard even excluding Necrozma. And then there's Kukui's extremely quick Lycanroc with Accelerock.
 

SugarCookie420

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I don't really think Pokémon games are generally that difficult, looking through a normal gameplay point of view. As long as you understand type match-ups, are at a passable level, and have the proper items to deal with situations, then all the game should be a breeze. Personally, I never had trouble with anything, excluding Battle Frontier-esque battles. I thought Whitney and Cynthia, two infamously tough battles, are heavily overrated, and I've defeated Red even though I was about 15 levels below him.

I believe what makes a Pokémon game "hard" or not depends on 3 factors:
1. How tedious is it to grind?
As I have said above, if you are at a passable level, you should be fine. The problem is how you should get to that level. What's the best place to grind? How long will it take? How under-leveled am I? What level is "passable"? Thus, games with easy ways to gain experience, such as the Key Item Exp Share games, alleviate the difficultly by a lot.
2. How am I playing the game?
My point above is based on a normal gameplay. There are many other ways to play a Pokémon game, such as Nuzlockes and solo-runs, which also include rules such as "no items" or "no Centers." No matter how easy a game is, the difficulty of the game depends on how you play it (eg you may have a tough time with Viola because you only have an underleveled Chespin).
3. How well do you know a game?
If you are starting a blind playthrough, or are new to the series, then any game could be a challenge for you because you don't know the proper way to fight a battle. I remember struggling with Emerald simply because I didn't know my type matchups, however fast forward 6 years, and I can easily defeat everyone because I know what they will send out, and how to counter it. If you don't know the game well, you may not have the right tool during battle (eg you don't have a good water type to deal with Malva, which you didn't know was a fire-type expert).

With all this being said, for me the hardest games were the first Generation games, since those games were different than future generations, grinding was atrocious unless you know glitches, and, for a person who didn't know much Pokémon when I first played it, there are moves that just don't work properly (Focus Energy, I hate you). All the other games I did have some trouble with initially, however as I became more familiar with the series they, including Generation I, became much more easier.

On the other hand, I've played a blind playthrough of X and Y, and beat it within 3 days without ever having to reset. I didn't find anything hard in that game, and since Exp Share is broken, I didn't need to grind much. This was also the point where Game Freak had started to baby the player a bit, something that I believe should be changed so that more experienced players like me have a much more challenging time. While I see all Pokémon games as simple, X and Y were by far the simplest.
 

Pyrax

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My vote goes to Platinum for its movesets and Pokémon choice. Take a look at Mars in Valley Windworks for example - her Purugly has high stats for that point and runs Faint Attack and Fake Out, both of which can be considered strong during earlygame. Then there's Cyrus carrying counters against his weaknesses (Heat Wave for Honchkrow, EQ for Gyarados, etc) during the Distortion World battle.
 

Arcanine10

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I'd say either Platinum or BW2.

As far as the easiest go, XY, SM and USUM (With the exception of Necrozma, of course) were a walk in the park.
 

Captain Hawlucha

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SM and USUM (With the exception of Necrozma, of course) were a walk in the park.
Do you have an explanation?

Anyway, I'd say HGSS. I don't know why, but they just gave me the most trouble.

BW because you can only battle in the stadiums at specific times of the day.

RSE. The Trainer's Eye trick was monotonous. I'm very glad the remakes fixed it.

In short I feel any game without reliable grinding methods is too difficult for me.
 
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