Mine is either Asking for It ft. Kurt Cobain by Hole or Wake Me Up When September Ends by Green Day.
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Hurt - Johnny Cashs Version (the video even more so)
These two for personal reasons, connected to some bittersweet memories:
Over the Rainbow - Israel Kamakawiwo'ole
Sharazan - Al Bano And Romina Power
"Maybe I'm Amazed" by Paul McCartney. Encapsulates exactly how I felt about my wife who died in December. Thankfully I know she knew, I'd played it to her and made her listen to the lyrics as a better way to explain how I felt than I could ever have put into words myself.
Leave Out All The Rest by Linkin Park
It reminds me of my husband and his struggles and I just sob every time I hear it.
The Ataris - The Saddest Song
Pink Floyd - The Great Gig in the Sky
That one song from Coco... Remember Me
That one song from How To Train Your Dragon... Test Drive
... just to name a few
The Loneliest by Maneskin. I watched the video and cried so hard I never watched it again. It is a very touching song
