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.

...on a personal plane, Punky's Dilemma....

( the whistling of the theme from The High and the Mighty on the fade-out just stitched me...)
Okay, so first of all Millercarbon is right. I’m sorry, but he just is. Margaritaville is one of the greatest, and deeply meaningful songs ever written full of exquisite symbols, imagery, and metaphors. But, I would suggest I’d Love to Change the World by Ten Years After. Or Reflections of My Life by The Marmalade. Or Isn’t Life Strange by The Moody Blues. 
A classic song about love,and love lost Marshal Tuckers classic 
Heard it in a Love song ,One good listen to its words, it hits it  home to the ♥️ and soul.

“Don’t you love her as she is walking out the door”!
nothing else comes close!
Imagine by Lennon is the liberal love song. No God no heaven?
 Title should be “Nightmare”!

Eve of Destruction- Barry McGuire - 1964
”Hate your next door neighbor, but don’t forget to say grace”.
Listen to Rick Rubin’s production of Johnny Cash……. American IV: The Man Comes Around 
and American V: A Hundred Highways. 
RUSH - 2112

A bad end for a citizen of collectivist state who shows initiative.
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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

California - Dreams So Real

"California falls in the sea,
that's when she said she'd come back to me."
two come to mind......

’Peace Piece’, Bill Evans......says it all with no words.

’Positively 4th Street’, Bob Dylan.....

everyone thinks it’s about them.

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+1 John Lennon - Imagine
Imagine by Lennon is the liberal love song. No God no heaven?
 Title should be “Nightmare”!
Meets the OP “The Most Philosophical Song You Ever Heard”, don’t necessarily agree with the philosophy.

If the OP means which lyrics spoke to one on a personal level, then that’s a different answer.
Guess the Band…

When a problem comes along
You must whip it
Before the cream sits out too long
You must whip it
When something's going wrong
You must whip it 
Now whip it
Into shape
Shape it up
Get straight
Go forward
Move ahead
Try to detect it
It's not too late
To whip it
Whip it good

Seems appropriate for the times…
Two songs off the top of my head:

1. The First Time - a love song hit in the 70s which was really a love song written in the 50s by a British man and great song writer, Ewan McCall for his life long partner Peggy Seegar, Pete's half sister.

2. And The Band Played Waltzing Matilda - especially as sung by Priscilla Herdman. It's an anti war song based on the World War 1 battle of Gallipoli, a terrible loss of lives caused by stupid generals. The words describe horror as the song proceeds and point out the futility of war as well as any song I've ever heard. Priscilla makes it especially terrifying as she has a beautiful voice and the contrast between her voice and the story only magnifies the lesson in the words. 
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Let us pause in life's pleasures
And count its many tears
While we all sup sorrow with the poor.

Guess that one without Google 
"I wonder If you can."

Also +2 for Imagine.
Imagine is commie pabulum, insipid nihilism, made all the more slimy for its silky delivery. A worse song it is hard to imagine. Okay, We Are The World. But that’s about it. Kharma Chameleon is more intellectually and philosophically grounded.
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"Imagine is commie pabulum, insipid nihilism, made all the more slimy for its silky delivery. A worse song it is hard to imagine. Okay, We Are The World. But that’s about it. Kharma Chameleon is more intellectually and philosophically grounded."

Good summing up, though I’m sure we can all imagine a lot worse than We are the World.
And yes, Karma Chameleon is leagues better.

However, John Lennon’s Imagine might still have a place in kindergarten.

It might even get some of these very young adults wondering why less than 1% of people own more than half of the world’s wealth.

We can, for now, leave Yoko and John’s personal assets out of this.

Champagne Socialism could be the topic for a future lesson.
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Leonard…darling of the right who are incapable of actually listening to..wait for it…..lyrics..

” Everybody knows the game is rotten, old Joe still picking cotton “..

Of course, when Ted is your great intellectual and bow hunter, quite a bit gets left on the table….
Todd Rundgren had (was in?  Kinda a fluid concept) a band called Utopia.   

On the album Swing to the Right the song "One World" offers a message of unity between all manner of common people. 

There is more (not Thomas More) but that'll do for now.
I have to agree with Miller about Imagine. Even when I was young it made me cringe.
What is it about grumpy old cynical men? Innkeepers with all the answers. Have no room in their closed minds for Mary or anything that challenges their insular shallow minds. And the irony is the OP's thread ostensibly relates to philosophy. 
Lennon's "Imagine" strikes a chord for hope and a better world. Christianity began as a communal sect. It's growth and success were limited by such a concept so it changed to a more realistic organization. Gained much by doing so but an argument could be made it also lost something important. My interpretation of Lennon's lyrics is they explore the true radicalism of Christ's message.