Continuation of my picks from the series that I started in the now-locked thread. No more than five from each generation that stand out, and I'm too lazy to post links.
Gold and Silver:
Even considering only original tracks and not the rearrangements from RBY this was really really
hard to get down to five.
Dark Cave. A killer bassline going and a good melody on top.
Goldenrod City. GSC is full of good town themes, it was so hard to pick one, and if you asked me on a different day I'd probably end up with a different one.
Tin Tower. One of three tower themes in the game that all share the same leitmotif (which also appears in other tracks), along with Sprout Tower and Burned Tower, and it just edges the other two out for the spot. Grandest of the trio and sets the occasion very well I feel.
Champion Battle. Yeah, do I really need to justify it? The early bars echo RBY's opening video music in grand fashion, connecting the start and end of the Gameboy era of Pokemon, before it goes into a pumping battle theme really befitting of the event.
Kanto Gym Leader Battle. This is pretty much the highest-tempo, most frenetic Leader Battle theme across the whole series, a real great.
Obvious (well, maybe) non-picked tracks:
National Park. It's a fantastic composition but I feel the Gameboy's sound chip doesn't quite do it justice. HGSS's rearrangement added a bit too much embellishment.
Dragon's Den. There's a good track under there, but buried by a screeching cacophony.
Game Corner. It's a really strong track, but the best Game Corner song in the whole series is Sinnoh's so I don't feel so bad leaving Johto's out.
Any route themes. Route themes in general usually don't stand out as much as battle, town, or dungeon themes for me. That's not to say GSC's are bad.