"Weird fashion shows"? The only real one I can think of was B2W2 unless you count the odd one-off strangely-dressed character, which is basically a series staple.
As for being the hardest, if you're willing to emulate it or have a Game Boy and a million bucks, Red/Blue were from back in the day when Nintendo was still coming off of its Nintendo Hard surge (think LTTP and Super Mario World-era) and had gems like how your opponents never run out of PP and the ease of accidentally activating a minor bug.
Best, in my opinion, depends on a few factors. If you like the "subtler" qualities of a game, like music and the real meaning of the story, BW is the way to go. If you're looking for the game's feel or graphics, I'd have to recommend X/Y or the Hoenn games (note: I can't say anything about the up-and-coming ORAS [DAWN OF THE NEGATIVE SECOND DAY], but Gen III was pretty solid.) If you're a sucker for gameplay, I'd have to go with Reudh on HGSS.
I meant the tournaments where you breed them for their cuteness.
The old ones are harder than the new ones :? Thats mildly amusing to consider, but I supposed that based on your loadout it could be. My only memorably hard moments in Red or Blue were the grind that was Silphco, occasionally Misty, and always Victory Road. My party was not equipped to repeated kill Gravellers who were typically at my own level. That said, the elite four was famous for one-shotting a few of my peoples. Not Gary tho.