Toughest Game from the past generations?

I kind of feel that the in-game difficulty of the Pokémon games have decreased Gen VI onward.
Which game, according to you was the toughest and why?

For me it was clearly Emerald cause of the ****in' Gym Leaders. It was fun, nonetheless.
 

Codraroll

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The proper answer is either Colosseum or XD. Double Battle-focused games where the opponents used actual strategies, where your own team selection was limited to most of the poorest 'mons to ever come out of Johto, and where you had to catch Pokémon in battles where they had partners that kept pommeling your 'mons.

As for the core series games... none of them are really that difficult. There's the ridiculous level jump in GSC between Gym 8 and the Elite Four, with no places to grind, which makes the Elite Four challenge quite hard... or rather, tedious to prepare for.

The reason why we feel the difficulty is decreasing, can mostly be attributed to our own experience. We learn what the mechanics behind a Pokémon's power is. As kids, we'd teach Alakazam Mega Kick, or Machamp Fire Blast. We'd happily believe that a move's power increased the more we used it, so we'd keep Thundershock on Ampharos instead of getting Thunderbolt or Thunder. We only had a vague idea about the type chart, never mind what the type of the various Pokémon were. We'd do so many mistakes that the games became challenging, but with the knowledge of a grown Smogonite, the games are a matter of "use the right move to OHKO the opposing Pokémon". We'd never dream of using suboptimal moves, or specialize our 'mons at the wrong end of the attacking spectrum. We build teams and pick moves to cover all our bases, when we see an opponent Pokémon we instantly know which moves would be the best to use against it.

To put it simply: We're too well prepared for the Pokémon games, and they mainly rely on the players' (lack of) preparation to create difficulty. Save from self-imposed challenges, the only way to have difficulty in Pokémon is a lack of preparation, and we're well past that stage.
 
I think the hardest games for me were Gold and Silver, mainly because I started playing them in Japanese as I didn't want to wait for the translation. Got stuck somewhere after the first gym because I couldn't figure out how to progress :D

I think Ruby had a moment too, with the Slaking in Norman's gym. I remember beating them with Rollout. My plan was just to get it so powerful it would OHKO.

Recently, I think Ghetsis and Cynthia from Black and White have been the only ones even remotely challenging. Probably due to the 'understanding the games better' mentioned above.
 
Personally the only ones troubling me are RBY and DP because of certain Bosses or mon distribution;
1) RBY had Misty's Lv21 Starmie. This thing OHKOes basically everything that doesn't resist Water and can even 2HKO Water resists. If you don't pick Bulbasaur and not grind at St. Anne's first, you're in for a tough fight. Heck, my Ivysaur almost lost to it in my first playthrough.

2) DP had no Fire-types if you don't pick Chimcar (OK, technically there's Ponyta but it's ...well, Ponyta). This is very annoying in a game where Bronzor and Bronzong exists to troll you as you find it very hard to OHKO them. DP also had very poor mons to choose from and had many repetitive mons (oh God, Bidoof, Bibarel, Starly everywhere)

3) Cynthia's Lv66 Garchomp. It's probably about 15 levels higher than your party when you fought it. Being a pseudo-legendary, it also had amazing stats. Have fun.
 
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To put it simply: We're too well prepared for the Pokémon games, and they mainly rely on the players' (lack of) preparation to create difficulty. Save from self-imposed challenges, the only way to have difficulty in Pokémon is a lack of preparation, and we're well past that stage.
Absolutely true, brother. I just played the Battle Factory on HeartGold, and got to a 20 win streak, no sweat(lost to hax). It just felt like a weaker version of the metagames we're so used to on PS.
At this point, the only "challenging" part of the games is the hax, and I'm sure all of us have encountered it at least once.

3) Cynthia's Lv66 Garchomp. It's probably about 15 levels higher than your party when you fought it. Being a pseudo-legendary, it also had amazing stats. Have fun.
Oh God that Garchomp. Sweeped my entire team.
*cue flashback to 8 y/o me almost snapping my DS in half*
 
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Celever

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The proper answer is either Colosseum or XD. Double Battle-focused games where the opponents used actual strategies, where your own team selection was limited to most of the poorest 'mons to ever come out of Johto, and where you had to catch Pokémon in battles where they had partners that kept pommeling your 'mons.

As for the core series games... none of them are really that difficult. There's the ridiculous level jump in GSC between Gym 8 and the Elite Four, with no places to grind, which makes the Elite Four challenge quite hard... or rather, tedious to prepare for.

The reason why we feel the difficulty is decreasing, can mostly be attributed to our own experience. We learn what the mechanics behind a Pokémon's power is. As kids, we'd teach Alakazam Mega Kick, or Machamp Fire Blast. We'd happily believe that a move's power increased the more we used it, so we'd keep Thundershock on Ampharos instead of getting Thunderbolt or Thunder. We only had a vague idea about the type chart, never mind what the type of the various Pokémon were. We'd do so many mistakes that the games became challenging, but with the knowledge of a grown Smogonite, the games are a matter of "use the right move to OHKO the opposing Pokémon". We'd never dream of using suboptimal moves, or specialize our 'mons at the wrong end of the attacking spectrum. We build teams and pick moves to cover all our bases, when we see an opponent Pokémon we instantly know which moves would be the best to use against it.

To put it simply: We're too well prepared for the Pokémon games, and they mainly rely on the players' (lack of) preparation to create difficulty. Save from self-imposed challenges, the only way to have difficulty in Pokémon is a lack of preparation, and we're well past that stage.
This is definitely a good point, but honestly I'm not sure how true it is. While we are prepared for newer games now so the overall difficulty of the franchise has decreased compared to when we were kids, we're all still very capable of replaying the older games with the preparation and practised skill that we as a community now possess. Difficulty does primarily lie in game design, and this is notably different throughout the franchise.

This topic can easily just be a "the boss fights are the hardest ergo it's the hardest game", but we all know that Pokémon is more than that. Distribution of Pokémon is a major factor, and diversity of major threats for each gym leader is also important. For example, in Emerald you get Pokémon like Lotad, Wingull and Shroomish quite early on who can all sweep Roxanne very capably -- and 2 of the 3 starters can do so too. Generation II, however, is much more different with Falkner only really being combated by Geodude and arguably Gastly. While we, as well learned smogonites, can just say "oh, let's head into Dark Cave and grab a Geodude", a lot of players won't think about that or just won't want to. For me, this means that Generation II has a much harder beginning to the game. I will also point out that Viola is in a similar position over in Kalos, but her team is genuinely weak. The Surskit hits like a water boatman trying to sink the titanic and the Vivillon isn't much better. BW2's Cheren is irrefutably the hardest first gym leader: no Fighting-Type Pokémon before it besides Riolu, who didn't learn any Fighting-Type attacks until Level 15 compared with Cheren's Level 13 ace. The best Pokémon to use against him is Azurill with Charm, which is a reasonably complex strategy for the first gym in the game.

Therefore, while we might still be knowledgeable players, it's easy to deduce that BW2 has the most difficult first gym. That's why I don't think this topic can be shrugged off as you did by saying players have improved more than the difficulty curve of the franchise, and there's a lot of discussion to be had here.

Personally, I think that Generation V are home to the most difficult games. Whether BW or BW2 is the hardest I'm in two minds about. Lenora is IMO the hardest gym battle in the franchise with few legit counters (Boldore or Sawk/Throh are about it; Pignite is decent but not bulky enough to take the Retaliate) and Elesa is also a big killer as she Volt Switches between something with only a Ground-Type weakness and Emolga, which are immune to it. However, beyond Elesa, the game gets much easier as the available Pokémon become more versatile and gyms grow more generic. BW2 has harder gyms throughout and, while there are more versatile encounters, these encounters don't necessarily equate to actual good options -- especially against gyms. You still don't have a major threat to Roxie by the time you meet her and she's a relatively tough fight. Marlon is the hardest 8th gym in the series except probably Claire, which is a feat when there are so many options available to take him out. I think this is mainly due to there not being that many options in the local area, but really for teams to not have Grass- or Electric-Type Pokémon by the 8th gym is kinda rare.

The notion that the OP presents is IMO untrue. The Pokémon franchise hasn't been getting easier as it's grown. However, I agree that Generation VI is pathetically easy, and actually I have friends who will agree, if we need another way to combat Codraroll's suggestion. I have friends who got introduced to the series in Generation VI and beat those games easily, but they downloaded Generation III to their phones and they found them really difficult. They still don't know the type chart off by heart, but they could easily make their way through Generation VI in spite of this. There has been a major difficulty decrease in XY and ORAS and it's a big issue if the franchise continues to be overcasualised.
 
The fact that Gen 6 hands you Game Breakers on a plate doesn't really help tbh (Mega Luke, Mega Kanto starters, Mega Lati@s).

I actually don't understand why you need to go to Dark Cave for Geodude when you can get it at Route 46 (I found it in my first playthrough) or trade for an Onix in the town. Pretty easy if you explore. In the games now, you don't even need to do that.

Marlon is tough? I think he's a joke of a leader.
 

Celever

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The fact that Gen 6 hands you Game Breakers on a plate doesn't really help tbh (Mega Luke, Mega Kanto starters, Mega Lati@s).

I actually don't understand why you need to go to Dark Cave for Geodude when you can get it at Route 46 (I found it in my first playthrough) or trade for an Onix in the town. Pretty easy if you explore. In the games now, you don't even need to do that.

Marlon is tough? I think he's a joke of a leader.
None of my friends used those game breakers because I told them it trivialises the game. It's still the easiest in the franchise by far.

Eh, Geodude is just so much more common in Dark Cave so it's usually worth it.

I said for an 8th gym leader. Generally when determining difficulty it's good to look at the start of the game, the end of the game and then look at any notable battles in the middle. Marlon is the toughest 8th gym in the game except probably Claire. This doesn't mean he's ball breaker difficult, because it's a comparison.
 

Cresselia~~

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I'd say Gen 1. I've never really played Gen 1 until how I recently bought Pokemon Green.
I'm finding it really difficult. It's not the language, since I've played Crystal to B2W2 in Japanese.
It's the lack of colors, and I have no idea which place is which place or what is what.
I can't remember the buildings because they all look the same to me.
I had a lot of trouble finding places, and I find it really frustrating.

I never found Crystal difficult, apart from the Ice puzzle in the Ice Cave. That was the only difficult bit.
I saved before battling Miltank, and I think I reset my Gameboy 3 times for Miltank. It wasn't that bad.
I've resetted more than 4 times for Elite 4 Will because I insisted on using Haunter's hypnosis.
I pretty much relied on haunter's hypnosis and Jynx's lovely kiss for my entire Crystal.
 
While it might stretch your definition of "main series" the hardest game with the same battling mechanics as main series by far is Pokemon Stadium (or Pokemon Stadium 2) - Rental Pokemon Only.

The Gamecube games at least gave you some concessions (i.e. you can change their movesets) to justify the difficult for a fair but hard game, the Stadium games are super hard metagame level movesets while you're stuck with pokemon deliberately created flawed (the rentals). Add in that the AI loves to screw with you (some of the "trainer" classes specialize in spamming 1HKO moves) and that the only decent pokemon are usually pre-evolutions and you've got a monster difficulty curve.

It's telling that you can pull every single gamebreaker from Gen 1 (wrap, Persian-slash, hyper beam, Psychic...) and it's still super hard. And then there's the sequel...

Sure, importing takes some of the bite off due to Mewtwo and the rest, but rental only is a nightmare.

For all pokemon media the hardest boss fight is Professor Oak from Pokemon Snap because HOLY BALLZ PROFESSOR I GOT A PIKACHU TO RIDE AN ARTICUNO YET YOU STILL HATE IT BECAUSE I'M OFF-CENTER YOU UNPLEASABLE MAN!
 
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One thing about Kalos that I've noticed now that I've played through it twice is that I didn't notice too much of a difference in difficulty from using Mega Lucario to not using Mega Lucario. Most if it really came from the fact that I shared more weaknesses than I realized.
Even without the gamebreaker, it is still easy to someone who knows what they are doing.

The proper answer is either Colosseum or XD. Double Battle-focused games where the opponents used actual strategies, where your own team selection was limited to most of the poorest 'mons to ever come out of Johto, and where you had to catch Pokémon in battles where they had partners that kept pommeling your 'mons.
...
To put it simply: We're too well prepared for the Pokémon games, and they mainly rely on the players' (lack of) preparation to create difficulty. Save from self-imposed challenges, the only way to have difficulty in Pokémon is a lack of preparation, and we're well past that stage.
This is very true.

While it might stretch your definition of "main series" the hardest game with the same battling mechanics as main series by far is Pokemon Stadium (or Pokemon Stadium 2) - Rental Pokemon Only.

The Gamecube games at least gave you some concessions (i.e. you can change their movesets) to justify the difficult for a fair but hard game, the Stadium games are super hard metagame level movesets while you're stuck with pokemon deliberately created flawed (the rentals). Add in that the AI loves to screw with you (some of the "trainer" classes specialize in spamming 1HKO moves) and that the only decent pokemon are usually pre-evolutions and you've got a monster difficulty curve.

It's telling that you can pull every single gamebreaker from Gen 1 (wrap, Persian-slash, hyper beam, Psychic...) and it's still super hard. And then there's the sequel...

Sure, importing takes some of the bite off due to Mewtwo and the rest, but rental only is a nightmare.

For all pokemon media the hardest boss fight is Professor Oak from Pokemon Snap because HOLY BALLZ PROFESSOR I GOT A PIKACHU TO RIDE AN ARTICUNO YET YOU STILL HATE IT BECAUSE I'M OFF-CENTER YOU UNPLEASABLE MAN!
While I did do surprisingly well with Rental 'mons (I did get the first three levels of Prime Cup with them and I didn't know what I was doing!), I could never get past Blaine in Gym Leader Castle until I had my own copies of Red, Blue, and Yellow and could use an Amnesia Mewtwo. And I had a tactic that worked well (Voltorb get a KO on first 'mon, then go boom! Electrode, go boom! VICTORY!).
 
For a main series game, I think Gen IV in general is really difficult. Diamond and Pearl in particular have an enormous level jump between the 8th gym and the E4, culminating the the most powerful Champion's team we've ever seen (the gap was somewhat addressed in Platinum, luckily). HGSS, of course, have the awful Johto level curve resulting in wild Pokemon being completely useless to grind against.

But I would also like to nominate Temporal Tower for the hardest final area of the franchise. It has:
-Porygon2 and Porygon-Z that have Agility and Discharge, which you have no hope of escaping
-Salamence and Metagross just wandering the hallways
-And, to top it all off, the Roar of Time-spamming Dialga as a hilariously unfair boss at the end.
 
The gen 6 gym leaders and rivals mostly have 3 moves on their Pokemon, if that's not proof they are becoming easier I don't know what is.

In Emerald I sometimes have trouble with Watson, Norman and Tate and Liza so I'll say that game. Even with a better knowledge of Pokemon as an adult, the gyms in Emerald are still very satisfying to complete, and don't feel like being tickled with a feather (gen 6)
 
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I found Gen IV to be the hardest main series games. I'm not sure if it was either the poor variety or the surprisingly good teams a few bosses had, but it was. I think it's the only one you have to overlevel to be sure to beat the Elite Four.

The other games can be easily dealt with with grinding, and well all know more grinding =/= more difficult.

That being said, Wattson in RSE (If you lack a Marshtomp), Tate and Liza in Emerald and Cooltrainer Jennifer in Ruby and Sapphire can tear some hair from your head. I guess RSE take second place, although it suffers from an erratic level curve.
 
None of my friends used those game breakers because I told them it trivialises the game. It's still the easiest in the franchise by far.

Eh, Geodude is just so much more common in Dark Cave so it's usually worth it.

I said for an 8th gym leader. Generally when determining difficulty it's good to look at the start of the game, the end of the game and then look at any notable battles in the middle. Marlon is the toughest 8th gym in the game except probably Claire. This doesn't mean he's ball breaker difficult, because it's a comparison.
Really? I personally find Drayden/Iris from BW to be a much harder 8th gym than Marlon -- there's not many ways to combat dragons especially without access to previous gen 'mon, and as soon as Haxorus gets one Dragon Dance going it's a pretty scary ride from then on.
 
Really? I personally find Drayden/Iris from BW to be a much harder 8th gym than Marlon -- there's not many ways to combat dragons especially without access to previous gen 'mon, and as soon as Haxorus gets one Dragon Dance going it's a pretty scary ride from then on.
Dragon Dance with Dragon Tail as STAB isn't really threatening though. Plus, Haxirua has poor bulk to begin with.
 

Karxrida

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The proper answer is either Colosseum or XD. Double Battle-focused games where the opponents used actual strategies, where your own team selection was limited to most of the poorest 'mons to ever come out of Johto, and where you had to catch Pokémon in battles where they had partners that kept pommeling your 'mons.
Colosseum > XD in difficulty. XD gave huge buffs to Shadow Pokémon so you benefit more from not having them purified, there's no early-game hell, you get a bunch of good Pokémon earlier, and the selection in general is much larger. Also, the first real boss has a Luvdisc.

It can still be pretty hard, though.
 
In the main series games, I would have to say that GSC are the most difficult games in my opinion. They have two gym leaders in Whitney and Claire who I consider both in the top 5 most difficult gym leaders. Also, as people have said, the level difference between the 8th gym and Pokemon league is a killer. Second place goes to RSE or DPP, but the brokenness of legendaries in those games makes the Pokemon league a breeze if you choose to use them.

I don't know if we are taking into consideration non-main series games, but if we are the Pokemon mystery dungeon red rescue team postgame is just a grinding mess. Most dungeons are not difficult if you have one high level Pokemon, but the 99 floor dungeons become tedious. Not to mention one sheer cold from a dewgong can end your campaign prematurely. Also, the level up curve makes it impossible to train up lower level pokemon which proves a problem in the 99 floor dungeons where you start at level 1, along with running out of pp.
 
I don't know if we are taking into consideration non-main series games, but if we are the Pokemon mystery dungeon red rescue team postgame is just a grinding mess. Most dungeons are not difficult if you have one high level Pokemon, but the 99 floor dungeons become tedious. Not to mention one sheer cold from a dewgong can end your campaign prematurely. Also, the level up curve makes it impossible to train up lower level pokemon which proves a problem in the 99 floor dungeons where you start at level 1, along with running out of pp.
This is why, once I clear the main story of Rescue Team, it becomes impossible for me to proceed any further without quickly losing interest. Not to mention the escort missions occasionally into sand or hail--and if you're not quick enough...
 
Yeah, I can only play pmd red rescue team like once a year. Regardless of if I die on floor 96 or if I succeed, the grinding gets real old real quick. The only thing that keeps me going is the catchy music and the fact that charizard is not only usable, but also the most viable Pokemon in the entire game.
 

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