Thread: Most Difficult Gym Leader in each generation?

Generation I: Misty (starting with a charmander and not catching a Pikachu is like suicide for the first 2 Gyms)
Generation II: Whitney
Generation III: No one. All of them were easy.

I Still don't have a DS (I will in soon) so I haven't played GEN IV and GEN V (yet)

Gen 1: Sabrina
Gen 2: Morty
Gen 3: Juan(Dang Kingdra was annoying!)
Gen 4: No one
Gen 5: Lenora( Retaliate hurts that early)

Gen 1: Sabrina(If Pokemon Stadium counts)
Gen 2: No one
Gen 3: Liza and Tate
Gen 4: Maylene
Gen 5: Lenora or Elesa(Friggin' Retalitate and Volt Switch!)

kanto:NO one was really hard for me, except for misty(if i chose charmander)
johto: hmmmm, clair
hoenn: norman
sinnoh: Fantina
unova: FUCKING ELESEA AND HER VOLT SWITCH!!!!!!!

Gen I- I think the toughest for me was Sabrina just becuase I could never figure out the warp tiles which made me so frustrated.
Gen II- Whitney, Miltank with rollout and milk drink was a nightmare.
GenIII- I played this Gen but have an extreemly hard time remembering anything about it all I remember is that I had saphire, started with torchic, had Kyogre, and almost lost the game cartridge which also made me cry.
Gen IV- Just got back into this but not really sure for toughest gym leader. Can't remember them.
Gen V- For me this might be a toss up between two choices number one Lenora- She actually beat me which surprised me even though I had my guys trained to good levels(I think 3 level 15 guys) choice 2 would be Burgh(can't remember if that is his name) surprisinglyI found him hard, his dwebble was destroying me. Then After completly overtraining (all guys to level 25) I just needed to switch who I had out and I would of been able to beat him.

Gen 1: Sabrina, I started with Bulbasaur and there was the whole balance issue with psychics there.
Gen 2: Clair, Kingdra had no weakness that I could hit at least with Miltank I had that Machop.
Gen 3: Wallace, that Milotic was a royal pain in the backside with all the recovering it was doing.
Gen 4: Fantina, mostly because the others were easy Mismagius was strong at that time of the game.
Gen 5: Drayden/Iris, wouldn't have made it out of that one without Ferrothorn. Those Haxorus hit like mac trucks.

Gen 1: ...no clue. Haven't played.
Gen 2: Only played the remakes (well, one of them), but MY GOD, BUGSY. You and your Scyther can go to hell, you little purple-haired git. O_O;
Gen 3: See Gen 1.
Gen 4: See Gen 1.
Gen 5: See Gen 1. X_X;

Generation I: I guess Sabrina? Such a pain in the ass.
Generation II: Definitely Whitney. Dumbass Miltank.. and the two Clefairy... (In Pokemon Silver)
Generation III: Norman.... Since I despised fighting Pokemon, it was of course very difficult for me. 2 Vigoroth and a Slaking didn't help at all... xP
Generation IV: It's either Gardenia or Byron. I had Turtwig so of course it was very difficult against the two of them... :/
Generation V: Lenora or Elesa. I hate.. h.a.t.e. HATE H.A.T.E. her freakin' Watchog... And Elesa.... Emolga. That's all.

Gen 3: The memory's a little fuzzy, but I think I had the most trouble with Winona. Flying-type Pokemon, Grass-type starter. Not good.
Gen 4: I don't think I had any problems with the Sinnon gym leaders. They were pretty easy to me.
Gen 5: LENORA.

Generation 1: (Only played Yellow) so probably Brock! Ugh Pikachu!
Generation 2: Like most everyone.... Whitney.
Generation 3: Brawley... especially with Sceptile O_o
Generation 4: Not really anyone...
Generation 5: Iris probably

Gen 1: No clue, I played but I can't remember if I had trouble with any one Gym Leader the most.
Gen 2: Whitney. Miltank + Rollout = Aaarghh
Gen 3: Hm. I don't think any of them were really too difficult, although Norman probably gave me the most trouble, whenever I didn't catch a Makuhita to help me through.
Gen 4: Uh. I just replayed this recently so I should be able to remember. I think Fantina might have been the hardest, although I did battle her during the night so no telling what state my mind was in.
Gen 5: I can't recall any Gym Leader standing out as being more difficult than the others.

Gen I: I only played with Pikachu and Charmander, so Brock was the toofest.
Gen II: goddamn whitney and her motherfucking rollout miltank.
Gen III: Tate and Liza -- I always had huge problems with them for some reason.
Gen IV: I always chose Piplup, so Gardenia
Gen V: Lenora, barely survived that one.

Nothing from the other generations sticks in my mind (then again I never played them past the first few badges except in SoulSilver :b), but Whitney and that freaking Miltank! Ugh. xD

Gen 1:misty, she ohkoed mmy bulbasaur with one bubble beam
Gen 2:Whitney and her rolling miltank and morty and his cursing ghosts..
Gen 3:Tate & liza in emerald..That claydol was impossible to take down..
Gen 4:none
Gen 5:the first 4 gyms!!

Gen 1: Sabrina...I HATE PSYCHIC TYPES.
Gen 2: Whitney, like everybody else said, that pink haired devil and her damn demon spawn with utters.
Gen 3: Oh my god, I think I had trouble with most of the gym leaders, but Tate and Liza took the cake...psychic types, AGAIN.
Gen 4: I think the hardest time I had was with Maylene, her Lucario kick my ass.
Gen 5: Although the easiest games I've played, I think Elesa was probably the hardest.