The Most Philosophical Song You Ever Heard


This may be a little too deeply personal for some, so reader discretion is advised. Don't know the reason, stayed here all season. Nothing to show but this brand new tattoo. But it's a real beauty, a Mexican cutie. How it got here I haven't a clue.
Blew out my flip-flop, stepped on a pop top, cut my heel had to cruise on back home. But there's booze in the blender and soon it will render that frozen concoction that helps me hang on.

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Fortunate Son, by John Fogerty & Creedence Clearwater Revival.  It speaks to me as I wore three stripes in the Army when it was released back in the day.
Just about every Townes Van Zandt song, but especially The Rake, The Ballad of Pancho and Lefty, Waitin' Round to Die . . .
Some of these songs seem to be sentimental choices rather than having anything to do with a particular philosophy. Getting a bit off track.
DMB (not sure if it is the "most" but it surely ranks)

Standing here
The old man said to me
"Long before these crowded streets
Here stood my dreaming tree"

Below it he would sit
For hours at a time
Now, progress takes away
What forever took to find


Written by Guy Clark, performed by Lyle Lovett (this one also is at or near the top of my list)

Here's a book of poems I got
From a girl I used to know
I guess I read it front to back
Fifty times or so
It's all about the good life
And stayin' at ease with the world
It's funny how I love that book
And I never loved that girl