I don't like winter or summer, I pretty much tolerate spring because it's not winter, so the only time of the year I really like is fall. Also, the music that I associate with fall seems to be some of my favorite...to me, that means stuff that's often depressing, but in an 'elegant' and abstract kind of way.
These are the albums I rock pretty hard all season long:
Basically the best black metal album of all time, but one that really transcends the genre. The three opening tracks are all it should take to become totally obsessed with black metal like I was. From the lo-fi production to the artful throat-shredding vocals, this album IS a forest losing its leaves.
There are very few things I don't like about The Cure, but these three albums define autumn to me. Some of their work is only good if I'm in a really bad mood ('Pornography,' 'The Top') and other things I only really play if I'm in a Cure-kinda mood ('Kiss Me x3') but I can listen to these three records all season long.
Just look at that goddamn album cover. Slow, long and moody pieces that feature really great (although totally out-of-place) female vocals. Somehow the simple vocal patterns and melodies make these songs feel like they stepped out of the 19th century, even though it's a doom metal album...
Best listened to at night by yourself. Creepy, abstract, weird, and emotionally muted. I guess these songs are depressing, but it's like a confusing, dream-state depression...cliche I guess, but it's like a David Lynch film. A word that comes to mind is 'secretive.' This is what I would listen to if I was an undercover detective.
Like 'Spiderland' with everything sucked out of it except the melancholy. This is less artful and more just straight up depressing. Not recommended unless you're feelin' real bad. I always listen to this while driving in the autumn dark with the windows down even if it's cold as fuck.
I never got past this album...as soon as I realized none of their other releases really had the full orchestra like this one, I didn't pay too much attention. I'm sure they're good 'n all...just not 'Ocean Rain.' Sure, it's sissy English-guy music, but it's way better than any Oasis or Ride or whatever.
Okay, this record is pretty good for any season...and I rocked it all summer long, but 'Smothered in Hugs' and 'Tractor Rape Chain' have this vibe that sits best with being way too stoned on a rainy fall morning. Maybe you're too 'grown up' to be in that situation, but I'm not.
I also tend to listen to a lot of 'classic' rock in the early days of fall...Creedence is such an earthy, forest-y kinda thing. I always get the feeling these guys wanted to blow up every city and just live in the fuckin' woods. Try listening to their version of 'I Put a Spell on You' and not feel cool.
Maybe it's because of Halloween, but Black Sabbath IS October.
The ultimate 'back to school' album....it IS 1972 and I AM trying to score a date to the homecoming dance when I hear this record. Usually I listen to side one of this, followed by Chris Bell's solo work. I love Alex Chilton and all he did, but the stuff with Bell has that chilly seasonal vibe...'specially 'Better Save Yourself' and 'I Am the Cosmos.'