They never get old. You listen to them on a weekly or monthly basis, even though they died out long ago.

For me, I first heard Stevie Ray Vaughn's instrumental only version of "Little Wing" somewhere around May or June of 1992 in Millington, TN when I checked into NAS Millington. One of my roommates had the CD "The Sky is Crying" which was the last album released by SRV's brother. "Little Wing" was not previously released on any other album and the track instantly stuck to me.

I never go more than a couple of weeks or maybe a month without listening to it. It's best listened to by yourself, wearing high quality headphones with a glass of bourbon and all the lights dimmed after everyone has gone to bed or their away on a trip.

Other honorable mentions are "Badfish" by Sublime

There are other great songs, but "Little Wing" has been the one that has never faded from my playlist.

What's yours, if you have one?

Tony.

For me, the oldest would the be the Johnny Cash songs I grew up listening to with my father: Orange Blossom Special, A Boy Named Sue, Ring of Fire, Walk the Line, Folsom Prison Blues, etc.

The next oldest would be my Pink Floyd albums, which Dad did not listen to with me: Animals, Wish You Were Here, The Wall, The Final Cut.

Sound of Silence- Simon and Garfunkel.
Right down the line-Gerry Rafferty
Sister Golden hair(surprise)-America
Into the mystic-Van Morrison.
Southern Cross-Crosby,stills and Nash.
Cool change-Little river band
I've got a rock n roll hear-Clapton

Fantasia soundtrack
Yellow Brick Road
Welcome Back My Friends
Jeff Beck
Surfing With The Alien
Night at the Opera

Comfortably Numb - Pink Floyd
And You and I - Yes
Stairway to Heaven - Led Zep
Awaken - Yes
Joe´s Garage - Frank Zappa
Why does it hurt when I pee? - Frank Zappa
Bobby Brown - Frank Zappa
Ziggy Stardust - Bowie
Five Years - Bowie
a lot of Bowie, Genesis, Peter Gabriel, Who, etc.

0-0

 
The Night They Drove Old Dixie Down, various artists, but mostly The Band and Joan Baez.

Blackberry Blossom, various (many) artists.

The entire Back in Black album

Red Headed Stranger

Blue Eyes Cryin in the Rain

War Pigs

Iron Man

That’s the short off the top of my head list.

Any song from Eat a Peach.

Lynyrd Skynyrd - Call Me The Breeze, What's Your Name, Free Bird, Gimme 3 Steps....

I'd have to think on it for a while, but off the top of my head:

-- Sultans of Swing by Dire Straits
-- Unforgettable by Nat King Cole
-- I've Got You Under my Skin by Frank Sinatra (Live with Count Basie at the Sands)
-- American Pie by Don McLean
-- Wreck of the Edmund Fitzgerald by Gordon Lightfoot (in fact, this is now one of my grandson's favorite songs )

My Old School

Baker Street

American Woman

Show Biz Kids

Hercules - Elton John

Hypnotized - Fleetwood Mac

Thick as a Brick

In Memory of Elizabeth Reed ("a song Dickie Betts wrote from our second album")

Hybrid - Finished Symphony. It was a Welch techno group that recorded the tracks with the Russian Federal Orchestra.
What they created is quite amazing.

It is hard to argue with any that have been mentioned. All absolutely great music.

the Outlaws.

Green grass and high tides

https://www.youtube.com/watch?v=hIaS_vYIQ_A

Johnny cash
Ghost Riders in the sky
https://www.youtube.com/watch?v=Mynzbmrtp9I


and one of my favorites

Ava Maria

https://www.youtube.com/watch?v=3d4xXvF2ukY

AC/DC.
Those about to rock, salute you!

most of the stuff from my high school years,


Costello
Numan
Zappa (big fan of Sheik Yabouti and a lot of his instrument stuff)
Morrissey/Smiths

and a few other never get old

A few off the top of my head:

Johnny B. Goode - Check Berry
Gimme Shelter - Rolling Stones
Whole Lotta Love - Led Zeppelin
What'd I Say - Ray Charles
Run Through The Jungle - CCR
La Grange - ZZ Top
It's Bad You Know - R.L. Burnside

I have a 4+ hour playlist of favorite drum-along tunes that I drum-along to at least once a week, usually about 2-3 hours at a time. Most all are 1970s-80s rock and/or blues.

Similar collection of guitar tunes to play along with, and then lots of other favorite songs that imo are either no good to play along with, are in non-standard tunings, or too difficult.