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Gen III's music I just love and think thats where Pokemon's music started to get good and Gen V's music is just wonderful as its got both epic battle themes and just tear jerking tunes such as N's Farewell.
It's tough. For me, nothing will beat the nostalgic feeling of hearing the Gen I/II music... but to try and look at it more objectively, I'll probably go with III. This also offers nostalgic quality, but the music really 'goes' with the look and feel of the towns and routes. The GBA quality doesn't even bother me - it adds something to it, in fact. Also Slateport City!
Gen V is pretty swish, especially the rival battle theme, but there are times when it gets a bit annoying. Castelia City is a bit hard on the ears, and when waiting to connect to the wi-fi for battles/tucking your Pokemon in, it's very repetitive. This is at the worst possible time, as you're not doing much else and the music becomes much more salient.
I have to say, though, that I don't care much for Gen IV. I don't hate it, but it's the weakest of the lot for me - it lacks the charm of the others, and unlike Gen III, it doesn't compliment the scenery to the same effect. It's kind of bland.
I like Gen.II for its new themes and beautiful remastering of Gen.I music.The new Rt.1 music sounds great beggining from a different point.Unfortunately they ruined Lavender Town theme.
I also like gen.V music like the ones in Nimbasa City and Black City.
Gen. V by far. White Opelucid was sooooo, soothing, that I sat there for ten minutes listening to the track and admiring it.
Also N and Ghetsis made me think, Holy oh my god this is epic. The background organs made it all the more epic.
But, I didn't like the Reshi/Zek theme. At first it was just a lighter, marchy version of the Red battle, but later it faded into a replica of the regular wild theme.
Although, I did like Hoenn, and HGSS' champion theme.
Generation IV's music was the BEST!!!! I loved the wild Pokémon battle theme and the Dialga/Palkia battle theme (Especially on the SSBB remixes!!!!), and the Team Galactic battle theme is just plain EPIIICCCC!!!!
I had to pick Gen IV. The Lake themes, all of Mt. Coronet, Team Galactic's themes, and the Sinnoh Gym Theme sold me. The HGSS themes were amazing as well, and I especially love the Johto Wild Battle theme. It's so epic!
Gen III and Gen V are a close second, however. They have great tracks as well.
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