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Who was the hardest gym leader for you to beat?

I mean out of all the pokemon versions who was the one gym leader that made you want to throw your gameboy/DS at the wall? Mine was sabrina back then in red version 'cause i picked pokemon on my team who had a weakness to psychic =/ like haunter, hitmonlee, nidoking.. Except charizard but he didnt do that well against alakazam. But that was back then when i was a rookie trainer. So what was your worst gym leader experience?
same here but i play on my laptop
 
I've always defeated gym leaders first try but Koga was annoying due to his Muk having Minimize. Tate and Liza got the closest to defeating me that Claydol is bulky as hell luckily Swampert held on long enough to double KO Lunatone and Solrock with a Surf
 
Well For each of the gens I play there is atleast one or more of those Gym Leader types!

Gen 1: that there Misty! with her over powered Starmie!
Gen 2: has 2 ( ironic I know huh?) The first being Milta---I mean Witney and that god damn dream eater rape Gengar of Morty!
Gen 3: has Watson if you chose Treecko also Flannery`s Torkoal! , but don`t get me started with those TWINS!
Gen 4: mmmmm Gen 4 is a though one as that is the gen I come back to the least but if I have to chose it would be Crasher Wake and his Gyarados if you don't have a Electric type to use!
Gen 5: is Definitely Elesa and CLAY! Elesa because of that Emolga! and CLAY because of -Say it with me!- EXCADRILL! freakin overpowered mole!
Gen 6: uuuum Until Today I never had any trouble with any gym Leader but if Elite four count than I had trouble with Wikstrom

soo Yeah that's all! ;)
 
I will always remember the terror Misty bestowed upon me with her level 21 Starmie. She would wreck my team due to the fact my Pikachu was extremely under leveled and that Water Pulse would wreck my Charmeleon who was only a level higher at the time, it got to the point where I would catch a full team just to weaken her Starmie to about half health until she used a potion to heal when my Charmeleon came out. As being the stereotypical fan boy of Charizard, it came with a price at the second gym in LeafGreen :(
 
Brock from Yellow. It was an impossible feat to defeat him with Pikachu. I had to get a Mankey and teach it Low Kick (It took me a while before I decided not to attempt to defeat him with Pikachu anymore).
 
Mine was Candace from Pearl some of you might think it was very easy to beat her but for me it was a headache :(.I was a rookie so I didn't have any good fire types(or moves in that case).I was always with grass types(They were my favorite type when I was in pearl)The one that beat Candace from my team was my grunt togekiss that i took seriously since then.The others from any game since or earlier were too easy.
 
Tate & Liza in Emerald, what you said earlier about throwing your system at the actually happened (I was and extremely emotional 8 year old) and i still hate lunatones and solrocks to this day. My Sceptile sucked and i forget what other pokemon i had at the time, but I hated them soooooo much.

Well For each of the gens I play there is atleast one or more of those Gym Leader types!

Gen 1: that there Misty! with her over powered Starmie!
Gen 2: has 2 ( ironic I know huh?) The first being Milta---I mean Witney and that god damn dream eater rape Gengar of Morty!
Gen 3: has Watson if you chose Treecko also Flannery`s Torkoal! , but don`t get me started with those TWINS!
Gen 4: mmmmm Gen 4 is a though one as that is the gen I come back to the least but if I have to chose it would be Crasher Wake and his Gyarados if you don't have a Electric type to use!
Gen 5: is Definitely Elesa and CLAY! Elesa because of that Emolga! and CLAY because of -Say it with me!- EXCADRILL! freakin overpowered mole!
Gen 6: uuuum Until Today I never had any trouble with any gym Leader but if Elite four count than I had trouble with Wikstrom

soo Yeah that's all! ;)
I hate Tate and Liza soooooo much
 
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Gen 1: Misty, had to try at least 12 times to defeat her.
Gen 2: Whitney, with her f***ing sky-high defence Miltank.
Gen 3: N.A. All was quite easy.
Gen 4: N.A. Haven't play it yet.
Gen 5: Clay, with his Excardrill he's soooo hard to beat.
Gen 6: N.A. Haven't played it yet.
 
Gen 1: Misty, had to try at least 12 times to defeat her.
Gen 2: Whitney, with her f***ing sky-high defence Miltank.
Gen 3: N.A. All was quite easy.
Gen 4: N.A. Haven't play it yet.
Gen 5: Clay, with his Excardrill he's soooo hard to beat.
Gen 6: N.A. Haven't played it yet.
i spent at least 4 hours trying to beat misty, and i couldnt even beat gary in fire red, but im alright now
 
Oh, let's see here...

In Gen I, I didn't ever have much trouble with any of the gym leaders, really. Most of my problems came from Lance and his Gyarados and Aerodactyl.

Gen II is, of course, the obligatory Whitney. I first played G/S/C when I was young (around the time they first came out), and I think I was actually reduced to tears on multiple occasions because of that accursed bovine. Also, I don't know why, but I have a feeling that Pryce gave me trouble.

Gen III was absurdly easy in terms of gym leaders. Really, the only ones who really gave me any inkling of trouble were, obviously, Tate and Liza, but they weren't too hard.

For Gen IV, I have to say Crasher Wake. Everyone else seems to have loads of trouble with Fantina, but Wake's Floatzel and its damnable Ice Fang make for an irritating time.

There were two in Gen V that I had problems with. Unsurprisingly, Elesa was one of them. Those Emolga are impossible to take out with out a Rock-Type move (at least, in my case it was like that). However, I also had an unbelievably difficult time against Cheren. Work Up devastated me several times before I finally finished him off.

Haven't played Gen VI yet, but none of the gyms seem terribly challenging to me.

Edit: Played through Gen VI. Korrina has a special spot reserved for her at the top of my personal hardest gym leaders. That Hawlucha of hers is absurdly OP.
 
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Kanto: Hmm...since when I played FireRed when I was 9, I only trained my Ivysaur so it was a way too high level for everyone so none for Kanto.
Johto: None. And after reading these comments, I am so glad I killed the Miltank before it used Rollout. Maybe Pryce...?
Hoenn: ...Didn't play long enough to get to a gym XD.
Sinnoh: ...Crasher Wake, my Torterra lost its resistance to Water so...yeah. I used way too many Hyper Potions on that battle... T^T
Unova: Just...Chili, my Snivy and Lilipup were under levelled, took 5 tries.
Kalos: Korrina...that freakin' Hawlucha's Flying Press, I am so glad my Pokemon were a higher level, but I used so many Hyper Potions. And I almost killed it and she used a Hyper Potion...GAH!
 
Unfortunately, in this generation, due to the great drop in AI difficulty and the easier leveling due to the upgrade to the EXP share, I just swept all the gyms, easy peasy. My Greninja had a little trouble in the grass and fairy gyms, but I just swapped out to Fabulous, my Pyroar, both times.
 
Probably Whitney in the original Silver.
(This not counting any gym battles in my previous and first game Yellow because I can't remember any of them).
Her and that damn rollout attack. Three tries at least it took me and finally was able to take her down by using a ditto to rollout her ass back. It was defeated but had done enough for my Crocanaw to finish it. That poor Ditto's reward was to spend the rest of it's days in the daycare as my breeding slave.

Again in Crystal, she was difficult. I remember it was Christmas and I had just gotten the Gameboy Advanced SP from my father. Since Crystal just so happened to be in my pocket which made it the only one I had on me I popped it in and proceeded to fail the Whitney battle several times. A cousin of mine (though oddly I'd been raised to call him my uncle granted he is too much older than me to think of as a cousin) actually asked to try it after watching me though he didn't know what it was and he failed too.

So it shocked the hell out of me when she turned out to be much easier in Soul Silver. Instead of rollout, it was stomp she spammed and still hardly utilized Milk Drink, in fact, I think it was potions she used like twice. So it almost wasn't worth it to start by poisoning it with my Skiploom. I can't remember who finished it.

Going back to the originals, Claire had also given me a hard time in Silver if memory serves.
 
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Gen 1 - Blaine and his friggin' fire-types!!!! Also, I didn't train my Pokemon that much..
Gen 2 - Chuck. AAARRGGHGHH!!!!
Gen 3 - Tate and Liza.. The ( *creepy voice*) TWIIIINNNSS!!
Gen 4 - Fantina. Made me hate Dusskull. ( forgot the spelling eeeee >_<)
Gen 5 - Elesa and her Emolgas. HOW COULD I KNOW THEY HAVE LEVITATE?!?!
Gen 6 - Don't own it! >_<
 
Gardenia is the cruelest person in the whole world. No lie. I hate her Pokemon, and I want her to DIE. Back in the days of being a rookie, I got to her and I thought I had a good team. That was until I met her. I had a Prinplup, a Bidoof, a Starly, a Shinx, and a Pachirisu. And possibly a Ponyta. Fail. Her Turtwig was easy with a Bide, but her Cherrim was another thing. I rarely got to Roserade. She caused me to go bankrupt! I had to resort to an Action replay to kill her. But oh my god, Gardenia is such a freaking witch, I'm not even kidding.
(This is a little off topic...) Not only is she cruel in that way, but did you know, that she killed her grandfather and her little sister to become gym leader?! This is the story: Gardenia really, really wanted to become gym leader, but her grandfather wanted her little sister to become gym leader, so she poisoned them. Then she thought of what she just did, then bought an antidote to cure the poison, but it was too late, so she threw it away in the trash, inside the Old Chateau... The proof of this is that you find an antidote in a garbage can in the Old Chateau... Game Freak never told that story in the game...

In B/W 2, I thought that Cheren was hardest to beat, because I only had like 2 pokemon, and had no pokeballs left... IKR, im such a n00b.. XD (Wow... this is one of the most lengthiest posts I've ever done...:-O)
 
Roark from my Diamond game. Even though I made it through, it took me a couple tries. (It was my first real Pokemon game.)
I had chose Chimchar, and he only evolved after that experience. I'm pretty sure the only other Pokemon on my team were Starly and my Budew. But once Chimchar learnt his first Fighting- move I was good to go.

Apart from that, the only other Pokemon game I've owned (from a hard copy) is Y. Particularly easy, but then there was the Psychic type gym (forgot the name) that was beaten on the first try, but destroyed my Lucario. Greninja helped alot.
 
I can't think of one in particular, but a few. Like OP said, Sabrina back in Gen 1 was awful. Psychic was so overpowered, since there were no ghost moves and only like 2 extremely weak bug moves that only maybe one or two Pokemon got. Koga's Venomoth that spammed Double Team always pissed me off too, so I just taught one of my team Double Team as well, and then also figured out to just use Swift.

Whitney was brutal back in Gen II, but in the remakes she's easier. Maybe I just know more now, maybe it's the increased amount of moves and the physical/special split or something, who knows. Clair's Kingdra can be tough as well, if you have nothing with dragon moves or didn't overlevel your team in preparation.

The psychic twins in Emerald I recall giving me a hard time.

And lastly, the first gym in White. I refuse to use the free monkey given to you that's super-effective against the gym, just on principle. So, I had nothing but my starter and a Purrloin against those Worked-Up Pokemon. It took a half dozen tries, when I usually beat nearly every gym leader on the first try.
 
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Bugsy. I found that Scyther with that Fury Cutter hated my Croconaw. Then I grew a brain (Idiotic one at that) and caught four Spearows to peck it to death. :D I have no trouble with him anymore, though. Next is obviously Whitney and Sabrina. You should know why already. Then, there is Morty... How I rue that Gym puzzle. I didn't even know that you had to find the invisible blocks until I restarted my game two times because I though it was a glitch! His team holds the same annoyance. Luckily, recently on SoulSilver, my Noctowl was the bane of Morty, being part Normal and having Confusion in her arsenal. :D But I still like Morty's personality, just hate the gym puzzle.
 
Gen 1 - Lt. Surge (Both RB & Y) - Its odd I know, but I didn't use a Digglett as I didn't want to get a cheap win. Plus his Raichu using Thunderbolt destroy my team one by one...didn't help that he out speed them too.

Gen 2 - Falkner (Both in GS/HGSS) - Not sure about you guys, but his Pidgeotto gave me more trouble than Whitney's Miltank.

Gen 3 - Nobody - Every gym leader in Hoenn was sadly easy to beat.

Gen 4 - Candice (Only in DP) - My team didn't get a fire type/ sixth member, until after the elite four. Her Medicham was the biggest issue for me and my team of five.

Gen 5 - Lenora - She was the only one that I can remember having an issue with in that region.

Gen 6 - Valerie - Where to start...well first I didn't use the exp share so I wasn't over level. My team was weak to the Fairly type moves....and her Sylveon with its creepy face, took down my team with a powerful Fairly move.
 

Rinoa Heartilly

Mother of Meltans
Freakin' Whitney. That Milktank is a force o' nature...
I found it really frustrating but after winning and getting the gym badge
from her, it felt like I more than deserved it. Some gyms are just too easy
but Goldenrod City gave you a run for your money.

[Talking about C/G/S btw~]

And then there is Bugsy with his killing machine, Scyther.
Holy Ivanova, he was definitely a challenge!!

So it's fun regardless, y'know? I enjoyed it! :'D
 
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voidaquariums

Formerly Luxray901
Well, Miltank was pretty darn easy. Two words: Roxie's Whirlipede. I had started with Snivy, and the only other Pokémon I had was a Purrloin. She beat me a bunch of times before I caught a Growlithe and a Pidove. Pidove died fast, but thank Arceus that Growlithe avoided a poison-boosted Venoshock to the face.
EDIT: I just remembered Elesa from B2W2. Stupid Zebstrika. *kick*
 
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NocturnalNetwork

Formerly LatiasMusic
Wallace on Ruby and his stupid Milotic. Norman was also hard. Slaking is stupidly strong,and the only fighting mon I had was a low-leveled Machop (that's now on my team,but at lv 59 and as a Machoke.)
 
None of them in gen 4 I paid my sister 5 bucks for every gym she beat for me i
ended up sitting on my @$$ and watching her beat all 8 I had to give her 35$ In return she even beat Cynthia and the E4 paying her 30$ 10$ for Cynthia I'll say use Drifblim it's a brick wall and he flies cut trees and has his signature trick use phantom force and fly :3
 
Oh man... Gym leaders... The hardest one for me was The Saffron City Gym Leader, Sabrina... In Pokemon Fire Red it took me weeks to beat her because she was just so hard!
 

AzureEdge

✧luzrov rulay✧
I'd say Wattson. I had a marshtomp and I was so under leveled, he beat me after his voltorb used self destruct. I had to train for days just to beat his team of electric types. But after that I had no trouble in any other gym.
 
I'll echo Whitney's Miltank from GS. Not as hard in HGSS for some reason, but I always had trouble in the originals. Bugsy in HGSS is always a pain for me. Even running with a Quilava it's hard. And what's-her-name in BW with the Emolgas. I like contact Pokemon, so Static and the like tend to be hard to work around for me.
 
In Platinum it was definitely Gardenia. In my last playthrough, I practically only had a Turtwig and a Zubat when I battled her. In Soul Silver, Whitney and Clair definitely are tied. Whitney's Miltank was as horrible as ever and I didn't have a lot of Pokémon that had super effective moves against her. In Black it was Burgh, Lenora, Elesa and Drayden. Once again didn't have any good counters to them. In Black 2 it was Burgh once again I did not have good counters. In X & Y it was no one. If I had to choose one it would be Wulfrick
 
tate and liza. somehow my pokemon have been WAY underleveled at that point and many of them were in their 30's. the gym was easy until they beat my ass and i was NOT expecting a hard double battle. i usually am good at double battles but my god they are demonic and i never EVER want to challenge them again.
 
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