The Most Philosophical Song You Ever Heard

Can't think of just one but I'll say Wish You Were Here

Wasted on the Way - Crosby, Stills, & Nash

1. The Who, "I'm One." For a 16-year-old struggling with everything 16-year-olds go through, a perfect song. 
2. Those great lines from "Under Pressure," including the cry from Freddie, "Why can't we give love/One more chance. . ." Such an old fashioned word . . . Dares you to too much.
3. U2, "Until the End of the World." Judas talking to Jesus, challenging his apocalypticism. "So Cruel" from the same album. Heck, "One" has some great lines, and a great premise. And from "The Fly": "They say the sun is sometimes/Eclipsed by the moon/I don't see you/When she walks into the room."

The Bruces’ Philosophers song from Monty Python.

”Immanuel Kant was a real pissant Who was very rarely stable
Heidegger, Heidegger was a boozy beggar Who could think you under the table
David Hume could out-consume Wilhelm Friedrich Hegel
And Wittgenstein was a beery swine Who was just as sloshed as Schlegel

There’s nothing Nietzche couldn’t teach ya ’Bout the raising of the wrist Socrates, himself, was permanently pissed

John Stuart Mill, of his own free will On half a pint of shandy was particularly ill
Plato, they say, could stick it away Half a crate of whiskey every day
Aristotle, Aristotle was a bugger for the bottle, Hobbes was fond of his dram
And René Descartes was a drunken fart "I drink, therefore I am"

Yes, Socrates, himself, is particularly missed
A lovely little thinker But a bugger when he’s pissed”

On a different level I’m rather fond of Who Knows Where the Time Goes by Sandy Denny

What's so funny about peace, love and understanding?

If we can throw in album titles, Bodeans - "Love and Hope and Sex and Dreams "covers pretty much every song ever written. 

Cheers,
Spencer