Quote:
Originally Posted by jonathanvaljean 
I recently heard "Puff, the Magic Dragon" for the first time in 25 years ...
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Not the saddest one for me but agreed, it really pulls at that "growing up" awareness that we have...
My honourable mentions:
Elgar's Serenade for Strings in E Minor op.20
The Slave Girl's Plea in Puccini's Turandot
Never Never - The Assembly (that love that always happens to someone else)
3rd Runner up: Boston - A Man I'll Never Be
2nd Runner up: The Stones' No Expectations - from Beggar's Banquet (for a twist, listen after reading Great Expectations' original ending)
1st Runner up: Boys of Summer (the video actually adds to the song)- Don Henley
Probably the saddest song? The Carpenters' "Superstar" -Loneliness is such a sad affair,...- Unrequited love, nothing left but the yearning and an empty horizon...