This is indeed a tough decision, and will need considerable thought.
You might want to make this a sticky...
So far what comes to mind for me with songs with significance to me:
Danny Cox...Danny Cox on Dunhill Records (1970) (especially "Train Song")
Hot Tuna...Hot Tuna on RCA (1969) (was released when I got my draft notice)
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Life is not a journey to the grave with the intention of arriving safely in a pretty and well preserved body, but rather to skid in broadside, thoroughly used up, totally worn out, and loudly proclaiming ...."WOW! What a ride!!!!!"
LUNCH with THEOLDMAN...On a break for now...