Problem with that is, I hate roggenrola. I despise them. Some people hate zubats and some people hate tentacool, but at least neither of them had sturdy.

 

I only played gen 1/2 as a child at which point in time I stuck to the strategy of letting my big red dragon (or fire dog) kill everything.

When I met Clair in Gold, I got fucked so hard. I eventually had to give my older brother like ten bucks when he 'bet me' he could beat her easily. He spent all my money on hyper potions. He x-defended, then took every single one of Kingdra's attacks and let it die to struggle. When she pulled the "not giving you a badge" bullshit, I thought the game was calling me out.

For the other generations I generally liked to grind and stay ahead so I never really had an overwhelming issue. Pokemon B/W was kind of a joke with the new TM system.

 

Watson is actually the gym leader that always gave me the most difficulty. It was stumping sometimes. Only if I didn't pick Mudkip though.

 

Whitney. Fuck Whitney with a rake. I could stomp the shit out of her Clefairy every single time, but as soon as that shitty Miltank of hers came out, shit was up in the air. It all depended on whether or not Quilava could outspeed Miltank, (which usually depended on whether or not Quick Claw procced) and how many times she got to use Rollout before I killed the Miltank.

This goes without mentioning that bullshit move Attract.

 

Haha yeah, I just barely got past Wattson with my team intact on my Emerald Nuzlocke run (aborted due to boredom after beating Liza and Tate). Took Torchic and didn't luck into a Geodude either.

 

In first generation, the biggest issues I recall having were Misty's Starmie and Sabrina's Alakazam. I started with Squirtle more often than any other Pokemon in Red so I rarely had trouble beating Brock or tackling Mt Moon. But Misty's Starmie would knock out by Butterfree's and Pidgeotto's without too much trouble. I vaguely recall raising Oddish's to counter. As for Sabrina, I only recall Alakazam being too fast and hitting too hard with Psychic.

In second generation, I think I only had a lot of trouble on Morty's Gengar and Claire's Kingdra. Gengar would be faster than most of my Pokemon and almost always hit with Hypnosis and Dream Eater. A devilish combination as whenever I didn't get hit with Hypnosis, the damage I did would be almost immediately undone. Claire's Kingdra was just plain strong without any easily exploited weaknesses.

In third generation, I believe Flannery's Torkoal and Norman (except for his second Slaking, the one that tries to spam Focus Punch) were the hardest. Torkoal had excellent defense. Overheat would almost always one-hit. To back that up though was a bloody strong Body Slam that had a ridiculously high paralysis rate. Norman's first Slaking and Vigaroth would hit and hit hard without fail (Facade and Slash, if I recall correctly). The level jump between Flannery and Norman is quite significant too since I usually have already fought all the possible trainers except for the Gym trainers prior to Flannery. After Norman however, the game takes a nose dive in difficulty until Victory Road/Elite Four.

In fourth generation, I honestly can't recall who was that difficult. Maybe Fantina's Mismagius or, if I started with anyone except Chimcar, Maylene's Lucario. I do recall the Team Galactic Admin or whatever in the Valley Windwork's being a huge pain with her Purugly. In HG/SS, either Bugsy's Scyther or Blue would be the most challenging. Scyther would wreak havoc with U-Turn. Blue is just such a significant step up from every other challenge at that point. I'll have to play this again as I've only done it once, sadly.

In fifth generation, obviously that damn Watchog. Up until after the second badge, Black and White are actually fairly difficult. Afterwards, not so much. I've never had much trouble with the Emolga's. First run I had a Krokorok who easily beat them, and the second time I had a Conkeldurr who took the hits but still won. I don't recall any real stumbling blocks after that, especially once you're given the Lucky Egg.

 

Whintey and that god damn Miltank!

 

In the first generation, I found the gym leaders to be, not exactly easy, but not unmanageable. I believe the biggest pains were Misty and Sabrina. Alakazam and Starmie gave me some difficulty, but I managed to off them with any major losses. I usually picked Bulbasaur for my playthroughs, so Starmie wasn't that big a challenge, and I had fondness for Dugtrio, so Alakazam went down fairly quickly depending on my levels.

Second generation was the one to nail me, and it was that goddamn Miltank with it's Attract and Stomp that always flinched me. To this day I still hate that damn Miltank >_<. I found Morty to be easy...because I usually had an Alakazam by that point. Clair wasn't that hard for me, I usually just status Kingdra and wail on it with Ampharos.

Third generation, I can't remember very well, I think it was Norman because the level gap between mine and his was pretty substantial.

Fourth generation I had no trouble breezing through the Sinnoh leaders. HG/SS and that fucking Miltank again, enough said. I found Blue to be somewhat easy, at that point I usually had my full team up, and I chose to rock Feraligatr generally, and it usually murdered his team.

Fifth generation, I found the toughest gym leader to be the first one because the levels of mine were on the low side. I never actually had that much trouble with Lenora. I usually just put something worthless to eat the obligatory Retaliate, and for some reason Hypnosis was hit and miss. After that I breezed through the game, because of the nice lady who gives out a free lucky egg.

P.S. Fuck Miltank.

 

Anybody who has ever had trouble with Morty just needs to take quick trip through the dark cave (whatever its name is) and head out around the Lake of Rage and nab a Girafarig. Turns Morty and his entire gym into a joke. Just watch out for Sucker Punch I guess.

 

Well, I'm planning on running through Emerald, Plat, and Black sometime soon so I'll probably post some updated thoughts on gen III, IV, V when they're fresh in my memory. From what I can recall though, only Brock in Yellow, Bugsy in Gold/Silver (Chikorita), and Gardenia (Piplup) in Platinum gave me trouble, especially with my lazy policy of only overleveling my starter.

 

Thinking of difficult gym leaders, only three really stand out.

Whitney, of course. Just fuck her.

Claire, who I would probably still be fighting if I hadn't realized that my Stantler knew Hypnosis and Dream Eater. Yes, I went through Gold and Silver with a Stantler. Still love that thing.

And last, there was Misty, who always sucks since I always pick Charmander. I remember that I managed to beat her by teaching Charmeleon Seismic Toss. This was back before I figured out the whole "switching your team order to train them all" thing, and only leveled up Charmander.

 

About Whitney, this picture sums up my feelings aptly:



This talk about Gym Leaders makes me rather nostalgic for Pokemon again... Anybody (other than Lungs, who never really gave up on Pokemon) interested in having a few matches again? Perhaps restarting the DLP League of Gym Leaders or what not?