My listening tends to fall into three main buckets: classic rock, alternative/indie sort of things, and classical. Stuff that straddles two of those categories, while rare, are particular favorites of mine.
A smattering of my favorite pop songs:
Song About The Moon- Paul Simon (one of his more obscure things- Paul Simon is probably my favorite pop musician overall)
The Underdog- Spoon (They're probably #2 after Paul, also I'm a sucker for horns)
Once In A Lifetime- Talking Heads
Every Day I Write The Book- Elvis Costello
One Of Us Must Know (Sooner Or Later)- Bob Dylan
Fight Test- Flaming Lips
Intervention- Arcade Fire
Come On Feel The Illinoise!- Sufjan Stevens (
Illinoise is probably my favorite album of all time; I'm a big fan of how Sufjan incorporates contemporary classical influences like Steve Reich into his music)
I Am The Walrus- The Beatles (yes, more than Revolution 9
)
All I Need- Radiohead
Stuck Between Stations- The Hold Steady
Tears of A Clown- Smokey Robinson And The Miracles
Fake Empire- National
And on the classical side of things, I like most eras but tend to prefer stuff from the late 19th-early 20th century, straddling the Romantic and early Modernist period. I also like a lot of contemporary stuff, which tends to be much easier listening than the pieces which turned people off in the 50s and 60s.
Bela Bartok- Concerto for Orchestra (This is, no exaggeration, my single favorite thing in the entire world. More than Dominion.)
John Adams- Violin Concerto (yes, a living composer- and almost all of his stuff is fantastic)
Igor Stravinsky- Petroushka
Camille Saint-Saens- Symphony #3 "Organ"
Antonin Dvorak- Symphony #9 "New World"
Olivier Messaien- Quartet For The End Of Time
Charles Ives- The Unanswered Question
Modest Mussorgsky- Pictures At An Exhibition (with or without the Ravel orchestration: my favorite version is actually using the Ravel orchestration but also restoring the missing Promenade, which is probably way more specificity than is healthy)
...And that's just the beginning. I'm a bit of music nerd, and still there are people who know ten times the things I do.