Only Time
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Me with komm susser todd because it personally relates to me heavily and how I feel about myself.
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Yeah I have a "sad" list for when I need to cry. These and Sweet Old World by Lucinda Williams and Road by Nick Drake, because he didn't find a road to take him home, and the stories about how he was so depressed he'd go into the studio and lay flat on the floor to record the songs.
John Prine also has that Sam Stone song, that is less poignant and more aggressively sad but so real sounding too.
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Build a Little World with Me - Laura Shigihara still hits me like a ton of bricks sometimes, but I'm also a total crybaby who has songs that I can literally break down crying just by reading the name of.
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Some Brazilian sadness: https://youtube.com/watch?v=r3PMqvqLyU0
The guitar is beautifully excellent
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My favorite go to sad song nuke is, strangely enough, "Alone Again (Naturally)" by Gilbert O'Sullivan
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That's the singer for the ending song for Plants vs. Zombies, and the theme song for To the Moon.
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Man. My friend was a huge Pearl Jam fan back in the day. I got my heart absolutely torn apart once, and he really helped me through it. When I just didn’t want to be alone he was down for me to come by every night and we’d sit in his garage and drink beers and smoke and talk, and he played me this song—now, I grew up on Pearl Jam in the 90s. Loved them. But I didn’t kept listening to them. He would sing this song every time we went out to any place doing karaoke.
But one night when I was avoiding being alone with my thoughts and he was there for me, he told me I needed to listen to that song again. He played it and Jesus Christ, man. I never felt so personally seen by a song I’d known my whole life.
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No better band to go to for truly heart wrenching songs.
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Poor old Jim's white as a ghost
He's found the answer that we lost
We're all weeping now, weeping because
There ain't nothing we can do to protect you -
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I would recommend you Chris Cornell's album "Songbook".
You probably know all the main Grunge bands but Mother Love Bone is not that well known. I totally would recommend!