The Ultimate Question?

I've thought of what might be the most important relevant/question, piece of information that a long time, serious, dedicated audiophile/music lover could ever wish to leave behind for an up and coming serious person to grab hold of and "grow"! Which 5 to 6 songs/half an album side would you leave for a serious person to hear and take away a serious series of songs to learn, grow, live from?
This might come by way of your life experience, socio-economic status, circle of life long friends,
I wanted to say, I'm still thinking, but here I go, ....
1. Has got to be something by Simon@Garfunkle, "America"!
2. Something from Robin Trower, "Lady Love"
3. Pink Floyd "Wish You Were Here"
4. Camel "Rajaz"
5. Iron Butterfly "Soldier In Town"
6. Black Sabbath "Faries wear Boots"
7. Extra... something from Nick Drake
I found myself wanting to start "side two" however, we'll see how it goes.
1. "Sad Cafe" by the Eagles

2. "Haitian Divorce" by Steely Dan

3. "Monday Morning" by Fleetwwod Mac

4. "More Than a Feeling" by Boston

5. "Simple Dreams" by Linda Ronstadt

6. "Before The Deluge" by Jackson Browne
This will be personal, very different for each responder. I'll stay with your lead toward Rock and Roll rather than blues and Jazz.

The songs I'm listing continue to effect me, even after years of listening.

(1) Joni Mitchell, "Song for Sharon"
(2) Bob Dylan, "The Times They Are A Changin'"
(3) The Doors, "Queen of The Highway"
(4) Roger Waters, "The Ballad of Bill Hubbard"
(5) Johnny Cash, "Hurt"
(6) Nirvana, "Plateau"
(7) Crosby Stills and Nash, "Wooden Ships"
The question implies that the wisdom is in the lyrics, which is limiting. With that in mine here's mine:

Robert Johnson "Hellhound On My Trail"
Sarah Vaughan/Clifford Brown "September Song"
Public Enemy "Burn Hollywood Burn"
Bob Dylan "Memphis Blues Again"
Charlie Christian "Stardust"
John Coltrane "Alabama"
This question is hugh and series!!!(sic)
Jimi Hendrix "Hey Baby"
The entire Cry Of Love Album by Jimi Hendrix
This is teh internet,
All of your serious songs are belong to us.
God! Where is the jazz? Classical?
1) miles Davis/ so what? 2) Julie London/ cry me a river. 3) yello/ blue green 4) john berry/ theme from "her majesty's secret service" 5) fritz reiner conducting the cso: last movement of scheherzade 6) frank sinatra/ fly me to the moon. Tough choices, I can do better if I were not in such a hurry to the airport!
I guess this is a your top 5/6 picks?
Well I love music so much and there is so much music if one is so inclined. I have xm at home and in the car so we know it ain't only about the fidelity/fer-me.
Females Karen Carpenter/ Connie Frances
Male Frances Albert/
Classical Dvorak/ Mozart/Beethoven
Love Dixieland/Country/Big Band Then on to 50's 60's 70's
Of course my list might be subject to change in 5days/weeks
Just play most any track from Dream Theater, they last 20 minutes lol