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-New Drink For the Old Drunk, Crooked Fingers

-And the Band Played Waltzing Matilda, Eric Bogle

-The Night We Met, Lord Huron

-Cleopatra, Lumineers

-The River, Springsteen

-Things the Grandchildren Should Know, Eels

-You Can't Put Your Arm Around a Memory, Johnny Thunders
An argument to be made that on pure 'sadness' grounds, the Crooked Fingers entry should be You Can Never Leave, but I think New Drink earns the spot.
Also, can't believe I left off Ode to Billie Joe
If you're going to listen to Things the Grandchildren Should Know, make it this live version, from Eels with Strings (I was there, am on the dvd somewhere in the crowd), which he closes by reprising Bride Of Theme at the end. This is a drink, man open.spotify.com/track/4g1DzKDz…
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