Pokemon games have always been easy, but most of us have faced

>>29604422
A few of them are still hard on subsequent playthroughs

>Kanto
I havent finished FRLG yet, but Iso far I'd have to say Misty too. I had a fire type, a rock type, a fighting type and a flying type. The battle was fucking hard.

>Johto
One of the harder regions, I could give you a story for any of these guys. Except Falkner. But especially Whitney. Every tiem I go in thinking "this will be easy now" something else fucks me over. I dont catch mons specifically to beat gym leaders and she always gives me trouble. In my current playthrough, all my mons were male, which was a real problem.

>Hoenn
In Emerald it was Tate and Liza no contest, like Whitney in Johto, it felt like they had a counter to literally everything I could possibly do. It was fucking hell. I actually broke my oen rule and left to train up my Vigoroth into a Slaking just for them. Norman was also an issue in both Emerald and ORAS. Nobody else gave me much trouble in the remake but Winona. and she was only notable in not getting one shotted

>Sinnoh
I cant remember much, but probably Fantina as well.

>Unova
Lenora and Cheren. Normal leaders are consistently harder it seems. Clay was kinda challenging in BW but easier in BW2. Lucario is probably why.

Nobody in Kalos. Also agree with Clemont

Misty because of charmander and not using a grass type.
Nothing was really that hard for johto. I traded for the onix, so no problems there. Not even the kanto leaders.
I was caught off guard by Norman. My mons weren't really at the point where slaking's bulk and strength were easy to take care of. Then he sends out the second one.
Winona's altaria and skarmory for bulk as well. I was using blaziken at the time and my team in general wasn't the best for handling them.
Steven's mega gets a mention in the remake. I did not expect it to run Giga Impact for sheer fuck you status. Took out my camerupt in one go.
Wake and that one ace trainer in platinum. I didn't have an electric type for gyrados.
Lenora for hypnosis and clay because I was using serperior without a fighting or fire type at the time. Excadrill was a problem.
Nothing for gen 6, but I used exp share just to see how over leveled I'd get on my first run. Korina giving me a second Lucario caused me a moral dilemma if that counts.

Elesa. Basically, her team slaughtered everything I used. Dewott obviously loses, Lilligant loses because of Aerial Ace/Flame Charge, Sandile lost because it has terrible defenses, Minccino lost for the same reason.

I remember having quite a bit of trouble against Wattson when I first played Emerald. Only had Grovyle and Swellow on my team, so his Magneton fucked my shit up.
Got me to grind up a Makuhita, which became one of my favorite Pokemon, so it's all good in the end.

>>29604422
>bugsy
but you get a geodude from the first route that demolishes the first two gyms

>>29605001
It was the first time I battled against him. I had no way to know that it would have been a good idea to train a rock type pokemon for that (and Whitney's) battle.

>>29604422
Gen 1: Misty/Koga- Can't really choose decide between these two. Whenever I picked Charmander, Misty always gave me a hard time, but I feel Koga was always difficult for me because of his extremely high levels compared to Erika and his minimize and toxic shenanigans with Muk.
Gen 2: Whitney- Ik i sound like literally everyone but fuck Miltank.
Gen 3: Norman- The Hoenn leaders never gave me too much trouble but Norman was definitely the strongest out of all of them imo with that hard hitting Slaking. It always made me nervous.
Gen 4- Gardenia/Maylene- These two were easily the hardest for me. If you don't pick Chimchar, Gardenia will most likely fuck you up, your best bet would be Staravia but if that dies, you're fucked. Maylene's Lucario was consistently strong and even if I picked Chimchar, she would still give me quite a lot of trouble.
Gen 5: Clay/Cheren- Clay was easily the hardest leader for me in B/W1. I hardly ever picked Oshawott so his Excadrill would just run through me. And don't get me started about Cheren's work up Lillipup.
Gen 6: Grant- The Kalos leaders were all fairly easy but Grant stood out to me. His dual fossil team was surprisingly strong and would usually take at least one of my mons down with him during our fight.