Imma just give a short review of the gens. I use the word short loosely.
Generation 1 (Red/Blue/Yellow): I've been a Pokefan since day one. You've never seen anything as unique as a monster trainer game at this point. The tunes were vibrant and catchy, but were epic and perhaps downright terrifying at times. Every Pokemon was unique at the time, and instead of the metagame being a giant competitive tiering battle, it was harmless fighting with your favorite Pokemon. Whether it's the ferocity of Blastoise's water cannons, the strength of Dragonite's hyper beams, or the rarity and pure power of Mew and Mewtwo, it was the sauce back then.
Generation 2 (Gold/Silver/Crystal): Although I didn't start off with this gen, it's my favorite. The graphics greatly improved and new Pokemon like Heracross, Umbreon, Tyranitar, and Scizor brought both cool and deadly options to the table. The music is arguably the best soundtrack of the series, containing one of my favorite video game songs of all time, National Park, as well as a chilling champion battle theme. Besides the new Johto, you can also explore Kanto, the region of generation 1. This is the only gen to include two regions too.
Generation 3 (Ruby/Sapphire/Emerald) + (FireRed/LeafGreen): Worst. Gen. Evar. End of story. But seriously, this generation was a total buzzkill. It had the easiest storyline, the least appealing/useful Pokemon (Exploud? Nosepass? Delcatty? Srsly?), and abysmal music. I honestly hate how the GBA portrays soundtracks. Too bland. Now, sure, there are some good Pokemon like Breloom, Metagross, and Sharpedo, but many of these are forgettable and downright terrible. At least they made up for it with a decent Red/Blue remake.
Generation 4 (Diamond/Pearl/Platinum) + (HeartGold/SoulSilver): This is the middle of the road (qualitywise) of the generations. On one hand, it introduced Wifi battling and revolutionized the Pokemon metagame. It also balanced out physical and special attack determination instead of basing it on type. On the other hand, its soundtrack was kinda meh (Excluding the G/S/C remakes, those were brilliant) and the storyline was forgettable. On one hand, you have great Pokemon like Infernape, Empoleon, Garchomp, and Bronzong. On the other hand, there are meh Pokemon like Luxray, Vespiquen, Skuntank, and Carnivine. Everything else is basically a new evolution of other Pokemon, not saying they don't look awesome though like Electivire, Weavile, and Mismagius. Just not as innovative.
Generation 5 (Black/White): Just a TAD bit better than Gen 4 IMO. Again, new features for Wifi expanded metagame possibilities, the editions of cool new Pokemon like Samurott, Archeops, Bisharp, and Co***rigus were appreciated, but others like Emolga, Garbodor, Stunfisk, and Klinklang are just lame. The storyline differs from the other ones as it actually questions the morals of encasing Pokemon inside Poke Balls. That could've been executed very nicely, but it was executed in the way of two characters (Hero and antihero) acting as a Ying-Yang, fighting over the right idea. To me, that just seems forced so the new legendary Pokemon could be brought in. The soundtrack is pretty good though with tracks like Tower of Heaven, the Elite Four Theme, and Route 10.
Everyone wants to be the very best in a franchise that is one of the very best.