I had a thought today while hauling the mail. (I do have those on the odd occasion)
It was the hour between my favorite radio shows and I reached for the cd holder to see what I could find to fill an hour. As I often do, I ended up with Tracy Chapman’s “Crossroads” from 1989. It’s one I never tire of. Like my Dick Gaughan “Handful of Earth”, I can listen to it anytime, it’s still enjoyable and not at all dated.
What music do you have that you listen to fairly frequently and have for many years.
I listen to the Sego Brothers and Naomi.
Planxty’s “Well Below the Valley” is a perennial favorite of mine. Also Liam Clancy with Tommy Makem.
When I lived with my parents I would dig through my Dad’s old records and listen to greats like Doc Watson, Jean Redpath, Emmylou, Stephan Grapelli, Brian Bowers, and Gordon Bok…among others. Folk music and Bluegrass will always have a place in my heart.
Metallica (pre-load), Black Sabbath, Pantera, Jimi Hendrix, Rage Against The Machine, Soundgarden.
Really though unless an album really dates badly (see some of the nu-metal stuff I bought in the late 90s) I listen to almost everything constantly. I may go a few months or even a year or 2 without listening to something but then I might pick it up and listen to it solidly for a week, depends on my moods.
Lots, actually.
Here’s a few:
Muddy Waters (50s singles)
Howling Wolf (50s singles)
Duke Ellington (Early 40s band)
Charles Mingus (About a dozen albums)
John Coltrane (A Love Supreme, Giant Steps)
The Beatles (Revolver, Rubber Soul)
Hank Williams (The singles)
Dick Gaughan (Handful of Earth)
Charlie Parker (Dials and Savoys)
Dirk Powell, Tim O’Brien & John Herrmann: Songs from the Mountain
The Beach Boys - esp Pet Sounds
Nine Inch Nails
Janes Addiction
Husker Du
Pixies
Anything by Brahms or Beetoven
Faith No More
Have to agree with Rubber Soul and Revolver by the Beatles
and anything by Tom Waits 
It would also be nice to have the young Rolling Stones/Led Zep back