This Is an Easy Battle.

Since me and my brother shared most our Pokemon games, I didn't complete that many gym leaders myself (I was more interested in the post-story arch and defeating the villains). I'd probably say Valerie from Kalos was a very easy gym leader and also gym in general. Most probably due to having my Steelix, but I was also disappointed at how easy the gym puzzle was and how weak her Pokemon were.
 
Brock in RB/FRLG since chances are you're going to have a type advantage with either Squirtle or Bulbasaur. I've never had trouble battling against Brock when comparing to other Gym Leaders at that stage in the game.
 
All the Grass gym leaders are easy for me cos the Bird Pokemon is usually one of the strongest ones in my team in every game.
 
Hm... First Gym Leaders notwithstanding, Byron from Sinnoh has almost never proven to be anything difficult for me at all. His ace (plus an extra Pokémon in Platinum) is horribly weak to Ground, plus the Fighting weakness, and his Steelix is weak on the special defense side. So there's that one.
 
The gym leader I had found to be easiest when it came to defeating would be Erika.

By the time we do get up to her, a lot of our Pokémon manage to reach a decent portion of level, even if we don't put much effort under training, which would be one reason behind this. On top of that, her team doesn't seem to know much hard-hitting moves, either; had they been different, I'm positive her difficulty would've been slightly more high.

Aside from her, I've also found Gardenia to be easy due to similar reasons; unfortunately, not many of her Pokémon had actually known much damaging attacks. As for most difficult, there are a few, with one being Whitney. Her Milktank was always a big challenge to take down.
 
I though Roxie from B2W2 was very easy. I beat her with only the magnemite I just caught and was only level 11. She can't touch you with her poison moves and Magnemite has Sonic Boom which deals 20 damage always. You don't even have to try there.
 
For me it is Falkner in GSC.

The TM given (and used) by this man is not even interesting, and his ace is leveled under 10. Plus, a Pidgeotto lv. 9 does not exist and its form at this level should be Pidgey. Say, maybe a lv. 14 Pidgey would have been better.
 
On R/S/E, Roxanne isn't much trouble when you choose treecko or mudkip and every major rock-type gym goes easy with grass/water starter. On HG/SS Bugsy be a breezy while you have flying/fire/rock to do a better pest control
 
For me it is Falkner in GSC.

The TM given (and used) by this man is not even interesting, and his ace is leveled under 10. Plus, a Pidgeotto lv. 9 does not exist and its form at this level should be Pidgey. Say, maybe a lv. 14 Pidgey would have been better.
Actually you CAN get a level 9 Pidgeotto, in a place called Viridian forest. It's a very rare encounter but you can run into one there and capture it, so the anime wasn't actually lying there.

For me it's Bugsy. The guy has a Metapod and a Kakuna! And the Metapod only knows Tackle! What Gym leader, let alone a second tier one, uses two unevolved Pokemon that only have Tackle and Poison sting? Give him a Ledian or something, not Metapod and Kakuna! At least he also had a Scyther but if you got a Flying type attack it's done for.
 
I've never had trouble with Erika because I always had either a Fire-type or Flying-type on my team that was pretty strong.
 
Last I took on Erika, I had a Fearow, which was able to hit for super-effective damage with Aerial Ace.

And Bugsy has that Scyther, admittedly, but that turns out to be easy mode if you have a Geodude on you. Otherwise...well, have fun.
 
Actually you CAN get a level 9 Pidgeotto, in a place called Viridian forest. It's a very rare encounter but you can run into one there and capture it, so the anime wasn't actually lying there.

I am against making wild (or trained) Pokemon appear when they did not reach the level required to evolve. It seems unfair.
But dat's another debate :/

I could also mention how easy I beat Misty in RBY, because I like Venusaur line so much.
 
Roxanne is really easy to beat with the starters, even if you choose Torchic. You can evolve it into Combusken and it becomes an easy battle. If you need support you can catch a Shroomish on the Petalburg Woods. You can catch a Marril too, you have lots of bets for this gym. Sure, it's the 1st gym, but it's too easy.

She isn't that easy if you try to beat her with only a Zigzagoon. That was annoying, it took me a lot of tries, and I had to use X Attacks in the end.

I think the easiest ones are Gardenia and Erika due to weakness against birds, Brock in FRLG thanks to weakness against all three starters (Charmander with its Metal Claw) and Mankey's Low Kick and Wattson, especially in RS, due to a lack of really strong Pokémon.
 
It took with few turns to kill his Onix with Metal Claw unless you get boosted attack from Metal Claw with Squirtle and Bulbasaur it be a breeze
 
On another note, with HGSS, Normal-types make Morty quite a bit easier, because his ace (Gengar) can only use Shadow Ball and Sucker Punch. I remember Marriland having a video that talked about how you could beat that thing with a completely untouched Stantler thanks to Leer and Astonish, and getting it out of Sucker Punches.
 
Bugsy what probably the easiest gym ever. I beat him with one pokemon. He was really awful with his bug pokemon which never even attacked me, apart from using string shot.
 
I think the easiest Gym for me had to be OR/AS Brawly, where I swept him with just a Beautifly. He was quite tough in the original versions, but they weakened his levels in the remake plus with Beautifly's Gust now being special it gets around Bulk Up's Defense boost.

Ramos in X/Y is also insanely easy if you're using any Fire or Flying-types, since his entire team is weak to those. When I played, it was pretty much a Mega Charizard X solo effort.

Korrina is also laughable if you're using a Ghost-type, as proven by a YouTube video where the player solo'd her with just a Golett (Honedge also applies here) because most of her moves are Normal or Fighting-type, which Ghosts cannot be hit by.

Skyla in both the 5th Gen games gets destroyed by pretty much any Electric-types, and it also doesn't help you can easily get a Zebstrika right nearby and wipe the floor with it. Brycen is also easy mode if you have anything super-effective against Ice-types.
 
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