Thread: Most Difficult Gym Leader in each generation?

Gen 1: Misty. That Starmie was horrific. I hated the thing; not only was it really fast, it hit so hard for so early in the game.

Gen 2: Whitney. Ugh, everyone knows why. That Miltank is the biggest ass in the pokemon world. Doesn't help in HG/SS it holds a Lum Berry, either >.>

Gen 3: I thought Norman was pretty hard, even with Truant those Slaking were still always ~4/5 levels higher, and had decent bulk and could hit hard. And once you had them beat Vigoroth would outspeed everything and just kill all your already weakened pokes. Tate and Liza were also pretty annoying to face, especially in Emerald with the Claydol and Xatu. But I think I'm going to go with Norman.

Gen 4: Umm, none were really that hard, imo. I suppose Volkner was slighty harder than the rest, so I'll go with him and his tricky Electivire.

Gen 5: Probably the first gym (whichever one you get). The type disadvantage is unfair, especially when I don't want to be forced to catch and train a silly Patrat or Lillipup to beat them or use the Dreamyard monkey, none of which I like. I finally managed to beat Cilan with just an Oshawott after many hours of trying though. Work Up + Vine Whip was murder.

Lenora supposedly causes trouble for a lot of people, but her Watchog never caused me any trouble whatsoever, so I can't vote for her. xP

1. Sabrina. I had to restart soooo many times because of the damn Alakazam. I always fought Koga before her, even though that's not the linear order.
2. Toss-up between Whitney and Claire. Coincidentally, they are two super-bitches with one wicked-impossible Pokemon and also won't give you your badge right away.

Gen I: I used to have a lot of trouble against Koga, especially in Yellow, where one of his Pokemon is at Level 50, and I had to loads and loads of grinding. I also always used to get poisoned by him in FRLG, but thankfully in Gen I, ground type moves work on his Koffing and Weezing.
Gen II: Whitney always used to be pretty difficult for me, especially when Rollout meets my Quilava. Thankfully, I normally defeat Miltank really quickly so that it doesn't get time to use Rollout in the first place. Also, Whitney's only weakness is fighting, so unless you picked up that Machop, it's going to be hard work.
Gen III: This one's a tie between Norman and Tate & Liza. Norman's Slaking used to be difficult for me, but now I just use the turn that Slaking slacks off for healing time for my pokemon. And as for Tate & Liza, I always found it difficult to take down their Xatu and Claydol.
Gen IV: I'm struggling to think of one, so I'll say Byron. Unless you have a fire type in your party, then your going to struggle against his Bronzor, as fire is its only weakness. But if I can count the gym puzzles, then I'd say Candice is the most difficult gym leader, with her really difficult gym puzzle.
Gen V: This is a tie once again, this time being Cilan/Chili/Cress, due to the fact that if you don't pick the elemental monkey in the dreamyard, you're going to struggle against their monkey, and Lenora, with her damn Retaliating Watchog, which pays back revenge for killing its fellow Herdier.

Gen 1: I dunno, they were all fine for me.
Gen 2: Whitney's dang Miltank, with it's stupid Rollout!!! First time my Typhlosion (Quilava then) fainted!
Gen 3: I honestly have no idea.
Gen 4: Volkner, I only had Gastrodon's Mud Bomb then to kill the Electric-types, and I had Platinum. Especially Electivire's Brick Break.
Gen 5: Easiest Gen, but it was Elesa for me, because of Emolga's Volt Switch, though Lenora was a close second.

Sabrina in Gen I was the hardest for me.
Gen II is Whitney, like the rest of the world, practically.
And Gen III goes to Norman. That Slaking... *shudders*
Gen IV... They were all kinda easy. Maybe Roark, cause I was lazy and never trained my pokemon high enough for his stupid Cranidos.

For Generation 3, I think Tate and Liza are surprisingly tough, since they have some strong Physical attacks, like Earthquake, and it's worse because almost all of their Pokemon can learn it (I only recalled Claydol doing it). Also, Norman's Slakings can really pack a punch, thanks to powerful attacks (Truant is a saving grace, thankfully).

For Generation 4, Perhaps either Gardenia or Volkner. Gardenia because my team wasn't very effective against her, but Volkner taught me the power of Focus Blast.

Thanks for reading.

Misty, Whitney, Flannery, Candice, Elesa... WHY IS IT ALWAYS THE GIRLS?!

Generation I: Definitely Sabrina. Her fast special attack pokemon always packed a punch against my lineup.
Generation II: For some reason, I always had a hard time with Jasmine. Maybe just my lineups. :/
Generation III: Watson...his Magneton always raped me for some reason.
And Generation IV: tough one... but let's go with Volkner. None were really tough for me in this gen. But he was a challenge.

Gen I - Erika and Lt. Surge - I had been using Squirtle, and only Squirtle as my sole battle pokemon, so I had to re-challenge them over a thousand times just to get their badge. At that time, I really had no knowledge on pokemon games, so Squirtle was just a battle machine :(

Gen II - I don't think there was a gym leader that I had trouble with. My first pokemon was Cyndaquil, and I hardly had any re-challenges using the fire-type starter. I guess Clair's Kingdra gave me a bit of a hard time, but I knocked her down with Typhlosion...which was over level 60 (again, lack of knowledge led me to abusing the starter pokemon in battles LOL)

Gen III - I didn't have much trouble here, either. In Hoenn, Winona's Swellow using Double-Team a lot drove me crazy LOL

Gen IV - Platinum - Byron kept killing my Rampardos :(

- SoulSilver - Of course, the toughest battle was with Blue (The last gym leader in Kanto). His team was awesome - I had to re-load the games multiple times...

Lenora, she never missed with hypnosis...so I was always dead.

Brock, I always chose charmander so I always had to evolve him to charmeleon (part was for my want of a charmeleon, the other part was that I always had to be at least lv. 13 in order to not be 2HKOed by Onix)

Gen 1: Even though I usually chose Bulbasaur, Misty was still pretty difficult. I couldn't beat her Starmie with one hit, so it would either heal, or take out half my HP
Gen 2: I always had trouble with Chuck. I don't really know why, I think he just sort of kept getting lucky, because now whenever I beat him, I do fine.
Gen 3: Tate and Liza. It took me FOREVER to beat them, they were the most difficult gym leaders I ever encountered IMO
Gen 4: Fantina always killed me. She still pretty much always kills me.
Gen 5: None of them were particularly hard. But Elesa's power switch Emolga's pissed me off.

Originally Posted by Phoenicks

In Gen III, was always Tate and Liza. The double battle meant that you couldn't just train one pokemon to the extreme like in other games (I learned that the hard way), and that Solrock and that Lunatone would never go down. It was harder in Emerald since they had 3 more pokemon, and it was hard to separate Solrock and Lunatone from each other.

ugh that was mine :X
Dear lord i've never had so much trouble with a gym before! and honestly, i think they are what every Gym Leader really should be, a challenge! :)
i only won against them the 1st time by sheer luck and i'm not afraid to admit that :X

Gen 1 - Misty. That Water Pulse was such a bitch it would always KO my Pokemon and if my Pokemon did survive 80% of the time it would get confused. Taking out its HP is not easy too.

Gen 2 - Whitney. Just like everyone else here...sigh

Gen 3 - Tate and Liza/Flannery/Norman. The psychic twins because of the typing of their Pokemon namely Solrock/Lunatone. It really was so difficult to take them out before either of them defeated one of my Pokemon. The double battle wasn't helping either since I always chose Blaziken. Flannery because of that Torkoal. Overheat! Overheat! Overheat! and it always looked like its stat never dropped. Its level is also a pain too. Norman because of Slaking and Vigoroth. Normal types always have high HP and this time it has high attack aswell. Its really hard taking them down and since he has 2 Slakings its even worse.

Gen 4 - Gardenia - Roserade due to its level and moves. Though I didn't have that much trouble in this gym compared to the others.

Gen 5 - Lenora/Elesa - Hypnosis, Take Down, Retaliate... I really hate this gym since I avoided catching a fighting type and it was such I mean suuuchhh a pain to get through this stupid gym. Elesa was not as worst as Lenora but that Volt Switch is really annoying and it does quite alot of damage too.

Gen I - Koga - Toxic/Double team so annoying.
Gen II - Claire - Kingdra using Double team, again it frustrates the hell out of me.
Gen III - Juan - Damn Kingdra did it again, but Juan's Kingdra is easier to counter than Claire's.
Gen IV -Volkner - Such a bad guy in Platinum with Electivire.
Gen V - Lenora - I lost to her on my first game in White. And I don't know why.

gen 1: misty or sabrina. I dont use grass pokemon, so I have a tough time on misty. also, pikachu sucks :P sabrina, I never have a good pokemon, and psychic isn't really weak to anything in blue and red.
gen 2: Claire. I never use ice pokemon, and dragon types are a pain to train.
gen 3: depends on the starter. Flannery if I pick Treeko (I dont get water pokemon till later. dont like the water pokemon choices) and always Norman, although it is somewhat easier if I pick Torchic
gen 4: hmmm... I've always done pretty well on these gyms. I'd have to say Fantina
gen 5: Drayden. I'm fine with the 1st gym, I just get my starter to about lvl 16 and I can usually solo it. again, I dont use ice types, and dragons are a pain, so the last gym is kinda difficult. I used to have trouble on Lenora, because of Takedown, and her last pokemon makes me fall asleep, but I just give a pokemon a Chesto berry.