Pokemania continues with something a bit out-of-the-box. Rather than doing a boss difficulty ranking or something, which has been done a thousand times and is highly subjective/variable, I came up with something a little bit more interesting/different that I haven't seen done before. This is NOT a ranking of the eight toughest bosses overall. It's me figuring out who the toughest boss (across the series) is for each gym number, to pick the toughest representative for each number and put them in a set of eight.
I'll be going off of the original versions of each generation, NOT remakes that came later. Most of the remakes nerfed quite a few of their tougher fights, with one big exception of Gen 4 beefing them up. For this list, the regular or deluxe versions count for determining the overall threat level of each gym leader. It's very telling that all of these are from the earlier games in the series...yeah, the challenge level really fell off a cliff as the generations went by.
Note: A hypothetical Pokémon game with these eight gym leaders as the bosses would be difficult, and likely quite unbalanced. If AI gets to the point where I can just have it generate a romhack with specific variables, the first thing I'm doing is changing a Pokemon game to have these eight bosses. Which Pokemon game, though? Which would best support this set of fights? That I don't know.
Gym 1: Cheren (Gen 5-2) - Normal type. The last of the classic 2D Pokemon series, Gen 5 is one I find to be very underrated. It's probably the most challenging generation overall, it's super high quality, and it generally got slept on. Cheren here is particularly strong for a first gym leader, and while he only has two 'mons, neither has any real weakness. Both of them can very quickly snowball their power levels by using Bulk Up several times (a strategy also used by the second gym leader in Gen 3, Brawly). It's imperative to get this guy's 'mons taken out within a couple of turns before they finish powering up and go on a Cynthia's Sword Danced Lucario style OHKO chain. Finally, there might well be zero Fighting-types available at this point in the game, meaning nothing to bring here with a type-advantage.
Honorable mention goes to Brock in Gen 1, though that's entirely contingent on either playing Pokemon Yellow or picking Charmander in the original versions of Gen 1. Under any other circumstances he's a pushover.
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Gym 2: Lenora (Gen 5-1) - Normal type. The underrated and delightful Gen 5 strikes again, and Normal strikes again. An honorable mention goes to Misty (Gen 1) who I always had issues with if I didn't pick Bulbasaur. However, far as the series goes, one Gym 2 leader who is inevitably a problem no matter who you pick is Lenora. She has another small team of two fairly unassuming 'mons. They're both evolved, at a pretty high level for this point in the game, and can put your 'mons to sleep with high accuracy. There's also a significant lack of Fighting types to counter her with at this stage of the game, so basically you've got little to nothing to bring here that has a type advantage. There are more Fighting-types available for this than there are for Cheren, at least.
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Gym 3: Whitney (Gen 2) - Normal type strikes yet again. Whitney is an infamous fight with an extremely tough ace, Miltank. Once it gets Rollout going, it's an OHKO-fest as it goes right through your whole team, getting stronger each round. And somehow it manages to pretty much out-speed everyone, despite being a rotund cow. The fact that she has another 'mon before Miltank is actually the saving grace here. It's subtraction by addition (for her) because it gives you some space to prepare. And if you properly prepare for Miltank, it's no problem at all, as seen here:
Most fights with Whitney don't go this well. The third gym is usually a tough one, as the level curve of enemies tends to spike a bit compared to the player, so figuring out who the toughest was in this category was a bit more difficult. Whitney is definitely the winner though.
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Gym 4: Elesa (Gen 5-1 + 5-2) - Electric type. The reign of Generation 5 continues. You want Rock types for this fight, and there are almost no decent Rock types at this point in the game. Usually Gym 4s aren't that bad, falling under the level curve a bit as your 'mons have now reached their second forms and some good ability range; this one really stands out from the pack for not being a pushover. Her 'mons pretty much keep your team paralyzed for the entire fight, ensuring that half your moves don't work, and Volt Switch lets her control the fight.
There's also a big lack of any strong Ground-types at this stage of the game. There's a reason they had her occupy this gym in both Black/White and its sequel - she might be the only gym leader to pop up in two successive games, much less occupy the same spot in both. Lastly, the best thing about Elesa is that her legs go all the way up. She's basically all leg, with a small body at the top.
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Gym 5: Fantina (Gen 4) - Ghost type. What a massive PITA this fight is. A minor asterisk for this one: This fight gets moved to Gym 3 in Pokemon Platinum, which makes it even more difficult. It gets a slight downgrade, but so does your party and your available options. That said, this fight isn't as bad as Whitney is at the Gym 3 spot, and I mostly know this fight from being in Gym 5 in Diamond/Pearl and the remakes. Since she's Gym 3 in the deluxe version of this Gen, she qualified to be on this list twice. She damn near pulled it off, but Whitney is just that tough.
Fantina though can be a nightmare of a fight, and no other 5th gym even got close to this one. It can go from under control to a disaster in a hurry, and just when you think you've won (after defeating her ace Mismagius), there's a weirdly OP Haunter at the end just to finish you off. Honorable mention to Norman in Gen 3, who nearly put another Normal-type on the board. I'd say he's a distant second in this category.
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Gym 6: Sabrina (Gen 1) - Psychic type. In Gen 1, Psychic was wildly OP. No other Gym 6 got close to the threat posed by this one. Seriously, go play Gen 1 again (particularly in the original forms, which this list is mostly derived from), and marvel at how much better Psychic is than anything else in the game. No matter what you bring, her 'mons are basically just going to walk through your team with Psychic attacks that nobody has any resistance to. Dark-type didn't exist yet. Alakazam is the second-strongest 'mon in the entire game (behind only Mewtwo) and it serves as the final kick in the pants here. It's level 43 and probably quite a bit higher than your team is. Bug-type does well against her, but good luck having a strong Bug-type around at this point in the game.
Oh yeah, and before you say Ghost-types... they weren't strong against Psychic yet, in fact they don't work at all. Whoops! This fight is an absolute drubbing. Fun fact: You can actually avoid all of the fights in her gym entirely with a certain route. They're all nasty psychic fights. Then again, you probably need the EXP from them for this fight, so...
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Gym 7: Tate and Liza (Gen 3) - Psychic strikes again. Two Psychic gyms back to back is definitely a balance issue in this hypothetical. Gen 3 is one of the easier ones, outside of this fight. This one isn't too bad, and it being a two on two can be a blessing as well as a curse. Their Claydol and its Earthquake is something that still wakes me up at 3 AM. What's worse than getting OHKO'd? Getting double OHKO'd. In Emerald they have two more 'mons than they do in Ruby/Sapphire and that makes a big difference. In either case this is easily the hardest fight of this generation outside of the final boss, so I don't know why they felt the need to make it significantly harder for Emerald.
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Gym 8: Clair (Gen 2) - Dragon type. With an honorable mention to Raihan from Gen 8 - also the 8th Gym, also a Dragon-type, and probably the toughest thing in the otherwise-easy Gen 8. Clair on the other hand has a lot more going for her. One of the toughest gym leaders in the series, and a rare 8th Gym leader that is actually difficult enought to be worth that exalted status. (The Kanto gyms in Gen 2 don't count for this project... Blue would be a contender here but he's really Gym 16).
All of her dragons are strong, but what really clinches this fight is her Kingdra. It's got incredible coverage that nullifies any advantages you might bring against her other 'mons, and it's so strong that I think the remakes of Gen 2 nerfed it down to a Seadra. Folks doing nuzlockes often hit a wall with this fight; one guy had to level a Lapras just to use Perish Song on Kingdra because he was out of options.
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Elite Four: None of the Elite Fours are particularly super-tough. In a way, they're just the trainer fights leading up to the boss fight with the Champion. If I had to pick a couple of tough sets, Gen 1 and Gen 4 come to mind. Especially the remake version of Gen 4, which probably handily takes home the gold for toughest Elite Four due to their EV training. Only in that version though. A similar thing could be said about the second Elite Four in the Gen 9 DLC, the Blueberry Academy. They, and the Gen 4 remake E4, are both a world apart due to being designed to fight competitive teams.
If we're looking at the original games and not any remakes or DLCs, then the deadliest Elite Four can be a more interesting compilation:
Lorelai (Gen 1) - Water/Ice type. The very first Elite Four member you fight in the entire series. She clearly exists to make a strong immediate impression and let you know that the Elite Four mean business. I always struggle with this fight more than anything else in Gen 1, except Sabrina perhaps. The type matchups are all wonky so often things aren't weak against what you think they are yet. Her 'mons combine Water-type and Ice-type to outstanding effect. You're at the mercy of RNG here, and if her attacks freeze you consistently then you're just boned.
Her ace, Lapras, is one of Gen 1's deadliest bosses alongside Sabrina's Alakazam and Lance's Dragonite. Electric-types tend to be the only thing with a chance here (so the various Pikachu-centric editions will be a bit less difficult), though in the various Lorelai postgame rematches she adds new things to lock out Electric's effectiveness. All around, Lorelai is just that much of a problem.
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Bertha (Gen 4) - Ground type. Pound for pound this is probably the easiest opponent in this list, for the position, relatively speaking. There just wasn't a lot of competition in the second Elite Four spot, and it seems like most of the second fights are pretty easy. It's probably intended to be a bit of a break. The only 2nd member who gave me any noticeable grief was this one. Bertha makes up for the first fight in the Sinnoh lineup, Aaron, being one of the easiest in the series. A Bug-type trainer? In the Elite Four?
Even in the original Gen 4 games pre-EVs, this is a really nasty fight. Her 'mons really like blasting you with Earthquake. Obviously there are ways to totally gimp this fight, but it can be an issue for less-prepared groups. And if we're talking about my hypothetical hack that includes all of these? Bertha is a good follow-up to Lorelai, because her Ground-types can nullify any Electric-types you brought for Lorelai.
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Agatha (Gen 1) - Ghost type. Back to the fights being difficult. Who likes spending an entire fight confused and asleep? Yeah, Gen 1 Elite Fourstrikes again. I think this fight is more about Gen 1 Jank than anything else. She's got a couple of Gengars that can outspeed you at all times, and it is actually possible to get Sleep'd for extended amounts of time and just straight-up trapped. Another thing about her is that she can totally nullify the effectivenss of a team that has been reliant on Psychic moves, which are of course the best moves in Gen 1 so chances are the average player will be leaning on them a bit by this point. Depending on the version/ruleset, and whether Ghost works right against Psychic, that nullifying can turn into total dismantling.
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Karen (Gen 2) - Dark type. A lot of folks would rank Lucian (Gen 4) here. Personally I had a lot more issues handling Dark-types in Gen 2 than I had handling Psychic-types in Gen 4. Coverage wasn't as good yet, and Karen's team is merciless. Her AI and movesets are better than the Gen 1 E4s so you won't get a break here with something using Growl, like you might with some of the earlier fights. If Agatha didn't already roflstomp any Psychics your team is relying on, Karen here will roflstomp them them the rest of the way. Psychic is totally useless here. Also worth noting is that she has some very strong coverage against various elements, without the accompanying elemental weaknesses (I don't recommend using Water or Grass). This fight is basically a cipher to figure out.
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Final Boss: Cynthia (Gen 4) - Balanced party. This one was no question, no final boss in this series has given me anywhere near the grief that Cynthia does. Usually final boss fights are almost a victory lap after getting through the Elite Four, but in Gen 4 the final boss is where things get really serious. Her Garchomp is the legendary one that's known for OHKOing entire teams, and the only way to take it down is to either outspeed her or have a 'mon that can survive a hit from her and retaliate with Ice Beam...and hope it one-shots. Even with Garchomp down, her other 'mons are nothing to sneeze at, with Milotic particularly strong and type-covered. While Garchomp gets most of the hype, Milotic is a second ace and might actually be her strongest 'mon.
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Postgame Boss: Red (Gen 2) - Balanced party. Not to take all of Cynthia's heat here at the end of the list, but if we're talking postgame uberbosses, there's no question Red from Gen 2 should be in that spot. Not only is he the toughest postgame fight in the series, he's also the coolest, and might actually be one of the best postgame fights in RPGdom in general. The main thing going for him are excessively high levels that your party probably won't be anywhere near, but even beyond that, he has really good type coverage. Honorable mention to the postgame Cynthia fights in both Generation 5.1 and 5.2.
Just realized that Red and Cheren are the only dudes on this list, breaking the absolute female dominance on the rest of it. That wasn't even by design, it just worked out that way.
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TOTAL APPEARANCES BY GENERATION
Gen 1: 4
Gen 2: 4
Gen 3: 1
Gen 4: 3
Gen 5: 3
Gen 6: 0
Gen 7: 0
Gen 8: 0
Gen 9: 0
TOTAL APPEARANCES BY TYPE
Normal-Type: 3
Psychic-Type: 2
Ghost-Type: 2
Electric-Type: 1
Dragon-Type: 1
Water/Ice-Type: 1
Ground-Type: 1
Dark-Type: 1
Omni-Type: 2
And of course, Fighting-Type...zero. Well, the dominance of Normal types early on made this a little less interesting of a boss set than I expected, but other than that I'm pretty confident in this list. The best part is that all of these ended up being from 2D games, so in theory I could put this entire set in a romhack of a single game (likely a Gen 5 game, or maybe Platinum) and have the game be able to support it.
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