Heh. Difficult Pokemon games. Alright, I'll play along.
I'm going to sound terrible, but...Red/Blue/Yellow. Seriously, go back and play them now, all these years later, coming off the 3DS titles...or even the DS titles. They've not aged well at all. Red/Blue slightly more than Yellow, given that Yellow gives you all three starters...although you also start with Pikachu, so if you don't know where everything is, or what learns what at what level, the first Gym is going to stonewall (haha) you.
Pretty much every Pokemon title from Gen III onwards spoils you shamelessly with significantly enhanced gameplay mechanics, a lot of hand-holding and signposts about where you need to go next, a wider variety of Pokemon along the routes, etc. Recently it's also been forcing gift Pokemon onto you and shoving you down linear routes to the next challenge with all the subtlety of a speeding locomotive. You can't not know what you're doing in new Pokemon titles, with everyone going out of their way to tell you...and roadblocks reminding you if you forget.
How was Gen 1 difficult?I just started it two days ago and I'm on my fifth badge,my nidoking knows Trash,Poison sting,Horn Drill and Horn Attack.I ran through the first 5 Gyms with just a Nidoking.Granted I have noting to deal with ghost types it's still pretty easy.All my other Pokemon are below lvl 20 excluding nidoking which is 50.