Neil Young/Tear Jerker

This Canadian musician has a few very emotional songs.

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• "The Needle and the Damage Done" is one of the saddest songs about drug addiction there is.
• "Philadelphia", particularly combined with the footage at the end of the film of the same name.
• "Sugar Mountain". Contrary to popular belief, this song is not about drugs -- but, rather, is pretty much a Growing Up Sucks song. Can make anyone feel wistful and nostalgic for their youth.
• "Transformer Man" sounds like a silly vocoder experiment, until you find out that it's about Neil desperately trying to find a way for his son Ben to communicate. Ben suffers from very severe cerebral palsy and cannot speak.
• "Birds". Just listen to it...
• "And After the Gold Rush". I've yet to hear a more melancholic song than that.
• "Let's Roll". You don't even need to know it's about 9/11...