"The Needle and the Damage Done" is one of the saddest songs about drug addiction there is.
Even sadder is the story behind it. The subject of the song was the guitarist of Crazy Horse, Danny Whitten, aged 27 at the time. Young found him immensely talented, but his heroin addiction ruined most of his life, including his playing. Neil hoped to get him back on track by inviting him to the sessions of his album Harvest (which the song is featured on, even if it was recorded earlier). The drugs had ruined him so much that he couldn't even keep in rhythm, much less play or contribute. Neil dismissed him, hoping to get Danny's life back on track gave him $50 and a plane ticket to LA to sort things out. The same night he received a call that Whitten had OD'ed. Young says it took him decades to stop blaming himself for his death. So much so that the next album he wrote Tonight's The Night focuses grief around the death of Whitten and Bruce Berry, a roadie and friend of Young who Whitten also turned to heroin, who died only months after Whitten. Young waited two years before releasing it.
"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. The version from the MTV Unplugged album can be particularly affecting, since without the vocoder, the lyrics are naturally easier to understand.
Similarly, "Daddy Went Walkin'" which sounds like a nice-going-on-trite little ditty... about Neil's father disappearing into dementia. Which, as he notes in his autobiography, may well be hereditary. The most gentle, loving Sanity Slippage Song you'll ever hear.
Old man crossing the road - you've got to let him go.
"Birds". Just listen to it...
"After the Gold Rush". I've yet to hear a more melancholic song than that.
"A Man Needs a Maid" is a very melancholy one specially in his 1971 BBC performance.
"Heart of Gold" is one of his most well known acoustic titles, and for good reason. Especially when one hears his live version, a sense of loneliness can be instilled into the listener if they also are searching for a heart of gold.
"Sleeps With Angels". It's about Kurt Cobain, and it can make you cry.
Neil wrote 2006's Living With War at a time when criticizing President Bush and the Iraq war was "endangering national security". He had seen a USA Today article praising the great scientific and medical advances the war had made possible... not a word about the pain and suffering being endured by the injured troops in the photos accompanying the article. He wrote "Families" — about a dead soldier's spirit reaching out to his loved ones — and three other songs that day. By the time he called his wife to hear them, he was crying so hard he couldn't sing or even speak. On the "Raw" edition of the record he is singing "Families" through tears.
"Ambulance Blues", the almost nine minute long closing song of his album On The Beach, is depressing in an almost existential way.
The entire album On The Beach is this in spades, which is part of the reason it remained unreleased in CD format until 2003. Other tear jerkers on that album include "Motion Pictures" and the title track.
There's also "Thrasher", which is beautiful but so sad.
"Borrowed Tune", though most of Tonight's the Night is depressing.
"Only Love Can Break Your Heart" lives up to its title.