Tough gyms

[Lord Scalgon]

I don't know if it was just me, but I remember I had a hard time beating Chuck (HG/SS). Mainly due to the hypnosis/focus punch combo. It was pretty nasty, but apparently Whitney tops that for that generation.

As for the easiest...this is really difficult for me to decide, but if I had to choose one, Erika, without a doubt.

 

[blue]

There are Four (or Five) specific Gym Leaders who stand out as tough to me, they are Whitney, Winona, Clair & Tate & Liza.

Whitney for obvious reasons, I think we all share the same dread for that Miltank. Winona proved a tough challenge when her Altaria set up a few Dragon Dances, especially when choosing Treecko as a starter. Clair with Kingdra was just always difficult to me, no matter who was on my team. Finally Tate & Liza was more so difficult in Ruby & Sapphire being the first double battle Gym Leaders with two highly resistant Pokémon, Lunatone and Solrock.

The others aren't so bad. ;)

 

[Fitzsy]

Norman, Norman, George Foreman! Circumstances involving a broken internal clock and a chance run-in with Pokérus have rendered my copy of Emerald unplayably easy (an amazing nearly legitimate Pokérus generator, too!) so I have no opinion on him in that game, but Norman's Slaking in Sapphire... Jesus & The Blowfish that thing was tough.

Death in the Clair, strapped to the electric chair... I mean no doubt she was significantly tougher in Crystal than in HeartGold just because of the limited methods of taking down Clair's Kingdra and because I was way dumb and little when I played Crystal, but that thing was still a bit beastly in HeartGold anyway!

If it weren't for my Throh, Lenora's Watchog would have been a nightmare, so that's a thing too.

As far as the Gyms themselves go, I've found that Sootopolis Gym and most versions of Vermilion Gym have the most tedious challenges!

 

[Lolkat]

Hardest was Whitney, spent an hour on it...
Easiest was probably that grass type old man in X and Y. Wiped his team effortlessly.

 

[starseed galaxy auticorn]

Definitely Whitney. The first game I played for Soul Silver, I couldn't beat her. It took me more than five tries to finally kick her sniveling little tooshy. lol I had to get a traded Machop you can get from someone in the department store.

The second game I played after restarting with my cheats, I creamed her with my Raichu with Brick Break. XD It took three hits. One hit to her Clefairy and two hits to her Miltank, but that was just because of my action replay though.

The rest have been pretty easy since I've had a solid team for each element (water, flying, fire and electric). I always keep my team balanced so to say, if I was beating a water gym, I'd have an electric type to cream them. I do have back up pokemon like a fighting type and a psychic type in Pokemon Y. By far, Whitney is the only one that has proven to be a real challenge to beat.

 

[DamienEros]

Whitney was in a class of her own. I really haven't had a difficult gym leader though. I remember beating Misty in r/b/y with Charizard. I just grinded and flat out over power the gym leaders in most games. More strategic with last few.