1. Out Go the Lights by Spoon. This song is the reason for this list. It started played in my car the other night and it still got me a little misty eyed, even after the 100th listen. It's not a classically "sad" song but to me it's filled with such resigned longing for something long gone that it hurts my heart. I always found Summer of 69 by Bryan Adams to be morbidly sad for this same reason.
2. Do You Realize by The Flaming Lips. Soaring strings and beautiful but basic truths make me weep.
3. We're In This Together by Nine Inch Nails. I feel like this is the least obviously sad song out of the bunch. If I was just reading the lyrics off a piece of paper I would think "Oh, a love song by Nine Inch Nails." But it's the way it's sung that is heart wrenching to me. It sounds like his voice might break from all the screaming in a few spots. It's like someone wrote a love song and then was asked to sing it right after they found out the object of their affection had slept with their best friend and murdered their childhood pet.
4. Wish You Were Here by Pink Floyd. Okay, so maybe this is a sad song if you interpret the person they wish was there was dead. But I never did. It always sounded more like someone who had lost a friend due to said friend making choices or changes in their life that they couldn't follow along with. Granted, when I first heard this song, I was about to make some decisions that would alienate someone I loved either way I chose, so I'm a bit biased about the interpretation.
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