1st Gen - Sabrina 2nd Gen - Whitney and Clair 3rd Gen - I did not play this Gen 4th Gen - To be honest, none of the Gym Leaders gave me trouble in this game 5th Gen - The Normal-type lady. I can't remember her name :/ I gotta replay this Gen
1) Brock. I've seen plenty of Charizard haters, but I had to beat him with my Charmander due to the fact that I had a goal of catch ONLY 6 (+starter.) I beat Sabrina easily with my lv. 54 Growlithe that I didn't know how to evolve.
2)All of them were much too easy. The most annoying was Falkner and his Bellsprout Tower.
3)Brawly. No super effective pokemon due to (again) the goal of only 6+starter. I beat him by level.
4)All of them wer again much too easy. Candice, however was the most annoying to get to. --- Gamefreak better add a feature that can topple this fairy type.
Honorable mention goes to Koga because there was a time Weezing used Self-Destruct on my last Pokemon making me lose because the game blacks you out when you have no active Pokemon left even though I technically won the match. Pokemon hasn't made me that angry since then.
II. Whitney Cry me a river, but Rollout is ridiculous if let get out of hand. Unlike Bugsy, she can't be beaten by a bunch of Unowns and a freshly hatched Togepi.
III. Winona I think Skarmory and Altaria were enough diversification to be annoying.
It's worth noting Emerald made several of them difficult. I'd note that Flannery and the twins were amped up significantly.
IV. Byron If you didn't go out of your way to come prepared for this one, a few hiccups are expected.
Honorable mention goes to Candice if you didn't bring one of the two or three Fire types available.
V. Elesa The Volt Switching was irritating both times I took her on. This was the only time I had to revive someone in White 2 making it noteworthy.
To the folks saying Drayden: pack a Crustle. I tore him down in one hit in both games. It's a simple but effective strategy. --- Go to Gamestop, buy a Steam card, and use it to purchase Ys Origin. You won't be disappointed. Don't reboot PCs that you cannot access.
1. None were really difficult. Misty was the only one that gave me any real issue, probably because I was still getting used to the game and Starmie just crushed me.
2. Clair. Kingdra being Water/Dragon left me confused as to how to deal with it. Whitney was simple and is overrated to hell.
3. Norman, easily. Slaking packed one hell of a punch I did not expect.
4. No gym really gave me trouble. Cynthia though...
5. No gym in B/W or B/W2 really gave me an issue. Well, none really more than the others I guess. All were built fairly well. --- However history remembers me, it shall only remember a fraction of the truth.
Gen 1: Sabrina. OP Psychics made things stupid difficult. Had to power train and beat her with brute force to win.
Gen 2: Whitney. Claire can be tough, but being that late in the game meant I had a couple of options. Whitney, on the other hand, sucks to fight. Nothing in the early game can tank well enough. Even my Geodude was slain....
Gen 3: Norman. Why everyone had issues with Liza and Tate I don't know, as I just spammed Surf to win. Norman, however, required me to actually use X items in conjunction with my Combusken in order to make it through.
Gen 4: No one. They were all easy for me.
Gen 5: Same as Gen 4. Not even Lenora could stop me. Decoy Patrat, you see. It took the Retaliate hit, then I just proceeded to stomp all over her. --- The only time a lawyer can cry is when it's all over.