Toughest Gym Leaders?

[J Greig]

So, I have played a lot of the Pokemon games. I have pretty much played from Pokemon Yellow up to Pokemon Omega Ruby/Alpha Sapphire (not played Black/White yet). What were your hardest gym leaders in the games? Every game you played, there was usually one gym leader which required you to level up a lot and/or learn new moves before you could actually beat them. Here is my list:

Yellow, Gold/Silver/Crystal, FireRed/LeafGreen, HeartGold/SoulSilver
MISTY! Unless you chose Bulbasaur, I had a pretty hard time getting past Misty. Although, I eventually found out you could catch Pikachu in the Forest, it still took a while to actually find and you ended up getting bored eventually. Being so early in the game, you didn't have many Pokemon, and you were only around the level 20-25 mark.

Gold/Silver/Crystal, HeartGold/SoulSilver
The final gym leader known as Clair! Of course, being the final gym leader, she was always going to be strong, but her dragon type Pokemon were unreal. It took me ages to finally defeat them. Her Kingdra was very strong and had brilliant speed and defense.

I won't go on to name them all, but what were the gym leaders you struggled against?

 

[Pyro]

I fucking hated that Kingdra. It always seemed to beat me somehow.

 

[Six Trails]

Kanto: Sabrina (Yellow) - Since special was a single stat in Gen 1, her lvl. 50 Kadabra and Alakazam were ridiculously broken and over-powered. Lvl. 50 is like Elite 4 tier (or should be).

Johto: Whitney and Clair (GSC/HGSS): Whitney because of her Miltank and rollout, and Clair because all of her Pokémon spam with Smokescreen and Thunderwave.

Hoenn: Tate and Liza (RSE): Can't go much into detail as I haven't played Gen 3 in a long time, but I remember them giving me the most trouble.

Sinnoh: No clue. I don't remember struggling with any, really.

I don't know any of the Unova or Kalos leaders.

 

[Pyro]

That Miltank can go fuck itself to death.

 

[kriss-]

Myself

 

[Satsuki]

Whitney's Miltank can kill itself.

 

[Frankie]

Playing all Gens through not long ago, I would say Whitney and that damn roll out, rolled my team 6 times and over again.

 

[Super Saiyan Overlord1007]

Gen 1

Sabrina - Psychic Pokémon were more broken than Dartz and his Orichalcos cards before Gen II depowered them a bit. Lv50 team? That should be Elite Four level or at least it was in later games.

Brock - Charmander was my favorite starter for Gen 1 before Bulbasaur took that spot. Pikachu in Yellow should speak for itself

Misty - Charmander as my starter = hard time, even with Pikachu I had a hard time. Bubblebeam is a one hitter quitter


Gen II

Whitney - Speaks for itself. Fuck that cow and her Miltank too.
Claire - With the only Ice Type moves you had access to being Ice Punch and Icy Wind plus Kingdra is a wall to pretty much anything you would have without cheating she was a serious problem. I remember my mom, sister, and I all took turns getting our asses kicked by Claire before finally beating her.


Gen III

Brawly - He was hard first time around and I didn't pick Torchic as my starter.
Watson - I prefer Treeko over Torchic and Mudkip sooo.... yeah (although I made sure to catch a Makuihata while in Dewford Cave)

Wionna - First time I played Gen III I picked Mudkip and got my ass kicked by that haxed Altaria everytime

Liza & Tate - Solrock and Lunatone were walls. Even with Super Effective hits I wasn't doing any major damage and them raising their special stats and having moves like: Ice Beam, Flamethrower, and Solarbeam wasn't helping at all.

Wallace/Juan - Their team wasn't a problem but Milotic was a problem. Good stats and spamming Recover...

 

[Clearin]

Brock is actually really easy to beat in Gen 1 with a Charmander. Onix has no rock moves and its special defence is abysmal.

Claire is a tough one considering her Kingdra is weak to only dragon moves, and chances are you don't have any of those.

Wattson if you pick Treecko and don't have a fighting or ground type, Magneton resists pretty much everything.

 

[Super Saiyan Overlord1007]

I was maybe 4 or 5 when I played Blue for the first time and I picked Charmander and I got put down a lot before just following my sister's advice on taking Squirtle. For Watson I always made sure I had a Makihuta or Hariyama at this point and it'd come in handy for Norman later on.

 

[Event Horizon]

Juan is the hardest, IMO. If you don't take out his Kingdra fast, you're in for it.
With the following moves; Water Pulse, Rest, Double Team and Ice Beam. Spams Double Team, if you manage to get its health low, then he simply uses Rest, wakes up immediately with its Chesto Berry.

Norrman is also somewhat hard. I don't have much problems with Whitney nowadays, but I struggled like fuck years ago.