Out of all the gym leaders, Gens I thru 5, which did you have the most trouble with? Post which leader was toughest for you, then explain what about them made them so difficult.

For me the hardest leader was probably Elesa from Unova. Her stupid Emolgas and Zebstrika kept using Volt Switch on my Specially Defensive weak team. I finally beat her when my Boldore got to level 27 and killed them with Smack Down.

I don't know about the hardest, but Norman is certainly the easiest (based on how highly leveled your team is when you fight him). The Vigoroth dies quickly, and you can just spam protect, detect, dive, or dig to render his two Slaking helpless.

For me, it was probably Blue in HGSS (never bothered finishing in GSC, so..). His levels are pretty high, and he has a diverse team. It took a little bit more than your average Gym to beat him, in my opinion.

Oh come on. There had to be at least one leader where you had some difficulty. There are like 40 of them!

Well, when you restrict yourself, any leader can be hard. On one of my Ruby playthroughs for example, I beat the Elite Four (and all preceeding leaders) with nothing but a Beautifly. In that playthrough, Wattson was a Mother******. You havn't been to hell untill you try killing a Magneton with one.

I think when I first bought Sapphire, I was really surprised how much tougher the gym leaders were than in G/S/C. Roxanne really took me by surprise. But, once I got used to them, it all became the norm again.

mine was whatever the normal gym in soul silver was. that miltank was from hell

That would be Whitney. Miltank was soooo hard the first tme I battled it, but I got a Machop every time after, so it wasn't as hard.

yea that miltank was killer. i soft reseted 12 times

Blue in HGSS was the only gym I ever lost to. I had nothing to counter that Rhydon O_O

when i played him i think i might of had some sort of water move on my pokemon

I think I caught Lugia by then and I Hydro Pumped it to death. His Machamp destroyed me with Fling+Iron Ball though (Aeroblast missed...)

I'm going to be honest, Roxanne and Brawly in R/S.

No matter how much I leveled beforehand, no matter if I was using Super Effective attacks they always gave me issues, whether it was that surprisingly bulky Nosepass or countless crit Karate Chops.

I acidently left my Lugia in the box

i hated burgh, really hard. and clair from my hg.

elite four... i could never get past the dark chick from gsc

Personally I think the psychic twins in emerald are hard + vs + + + =

I'm kinda like Mektar, I've only really found gym leaders hard when I restrict myself. It took me several attempts and lots of grinding to get past Brawly with a team of Mightyena and Linoone (at that time, Poochyena and Zigzagoon). Same with Wake's Gastrodon, when I used a Bibarel and a Luxray (For challenge playthroughs, I always use Pokemon in pairs).

On a first attempt though, Wattson was probably the hardest. For his Magneton, I had to whittle down his special defense with Psychic, then switch to Grovyle to Leaf Blade him down. Managed it on my first go, but only barely, and with a critical hit. I would definitely had found Wake's Gyarados very hard to beat on my first playthrough, but somewhere round Mesprit's Lake I discovered I had TM Rock Tomb, so I taught it to Infernape and it ended up being decently easy.

Thanks for all the responses! Now you can post both which Elite 4 and Gym leader was hardest.

My toughest Elite 4 was probably Phoebe from Ruby/Sapphire. All her pokemon had insane defense and coverage moves so it took me forever to beat her.

Juan in Emerald was pretty hard.

I also had a hard time with Marshal in B/W.

Well Emerald was easy cuz I had Sceptile and Gardevoir, who together can sweep through the entire Elite Four. After that, I learned competitive Pokemon, and elite fours became walkovers.

The toughest time I've had with the elite four was trying to beat it with a Blissey on Diamond. I was doing fine until I got to Cynthia, when she somehow predicted all my moves and ended up cornering my Blissey with her Lucario. She's damn tough.

I found Brawly on Emerald really tough, but my personal hardest Gym leader was Jasmine from HG/SS. She swept through my whole squad, and my main point, my Quagsire, was destroyed by Steelix...

The hardest elite four for me was Aaron. Damn my only playthrough of platinum being a solo run with a lotad!

Lorelei in Firered was a for me. The only decent pokemon I had was my Charizard, and even at level 92, her level 50-something Dewgong kept killing me. I finally beat her with a Poliwrath and Mewtwo, but that was really, really hard.

Clair in GSC/HGSS is the WORST. MOTHEREFFING KINGDRA'S TYPING IS WAY TOO HARD TO TAKE DOWN! Feraligatr's Ice Fang can really help, but once I get to Kingdra I'm screwed...

I'm not sure if I found any specific gym leader immensely hard. I know some gave me a bit of difficulty, but nothing to bang my head against the wall on. Perhaps if I go through the list and name my least favorite from every region I might get inspired.

Kanto - I'd probably have to say Koga in Yellow, or even possibly Sabrina. Their strongest Pokemon are both level 50, and they like spamming Psychic quite a lot, which makes for a very frustrating encounter. Koga's pretty easy in R/B, but in Yellow when all his Pokemon know Psychic and I think Toxic as well, it begins to get very irritating.

Johto - Whitney. I admit it. I picked Quilava and I found that Rollout to be positively evil.

Hoenn - Tate and Liza. Normally I would say Brawly, but after learning a neat little trick (from someone here, no less) that involves a small little Pokemon named "Sableye", you become literally untouchable when you fight Brawly. However, in Emerald when the difficulty of gym leaders escalates significantly, the fact that not only do all their Pokemon float, but all of them except for Xatu spam Earthquake, makes for great frustration.

Sinnoh - Maylene. Accursed Lucario.

Unova - Lenora. Unova actually surprised me immensely - I found every single last one of the gym leaders easy, except for the first two. Granted I was planning to do a 3-starter run in Black and left my Pansear deliberately underleveled because of that fact, but even without that I found access to only Incinerate as an SE move to be very annoying. ...wait, I'm not here to talk about Cilan. I'm here to talk about a Watchog that's most likely faster than anyone you have at this point and that knows Retaliate. I suppose if I'd caught a Sawk, the fight would have been that much easier...but I did.

Overall...Maylene. DPPt has a rather mediocre movepool of Pokemon to pick from, and coupled with the fact that Lucario is a very fast Steel-type (that shouldn't be Steel), it's made me headbang a lot. (And my starter was Piplup, if that makes any difference.)