I'm not sure which one is the saddest but here are some pretty sad songs:
1) Penfold - I'll Take You Everywhere
2) Sunny Day Real Estate - Killed by an angel
3) Brandtson - Holly Park
4) Brandtson - Potential Getaway Driver
5) The Get Up Kids - Valentine
6) From Autumn To Ashes - Short Stories with Tragic Endings
7) Thursday - [Most of the songs in Full Collapse Album]
8) Dead Poetic - August Winterman
9) A Thorn For Every Heart - A Night To Remember, A Morning To Forget
10) Snow Patrol - Run
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