This [[Music/NeilYoung Canadian musician]] [[{{Understatement}} 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 ever made.
** The story behind it is even sadder. The subject of the song was the guitarist of Crazy Horse, Danny Whitten, aged 27 at the time. Whitten had chronic pain due to arthritis, had found that only heroin helped, and had become addicted. Between the pain, the stiffness and the drug, Whitten's life and playing were ruined. With a doctor's help he quit heroin but was prescribed Valium for the pain, and may have become addicted to that. Neil, who recognized Whitten's immense talent, 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, so Neil dismissed him. Hoping to get Danny's life back on track, Neil gave him $50 and a plane ticket to LA to sort things out. The same night he received a call that Whitten had taken a combination of Valium and alcohol that proved to be fatal. Young says it took him decades to stop [[ItsAllMyFault 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.
*** Whitten's overdose occurred during the kickoff for the tour where he recorded ''Time Fades Away'', and one could easily assume this might have been the origin of a truly cursed period. Young was grief-stricken, his new backing band the Stray Gators was a train wreck, and his heavy alcohol use destroyed his voice. This was bad enough that Young even brought on [[Music/CrosbyStillsNashAndYoung David Crosby and Graham Nash]] to help complete the tour. Songs like "LA" can be interpreted as directly about the tragedy. The album was out of print for many years, and the stated reason was that it was recorded directly to an early digital mixer and suffered from horrible sound quality. Some have argued that while this may be true, Young's reluctance to release it again may be for reasons of grief.
* "Old Man". The song was originally written for the elderly caretaker who sold Young his ranch and was flabbergasted that a young man like him could afford it, so it likely wasn't intended to be as sorrowful as it turned out to be, but the music has ''such'' a melancholic tone that it can't help eliciting feelings of nostalgia, despondence, and a deep sense of longing. The haunting guitar motif instantly dispels any notions of this song being uplifting.
* "Philadelphia", particularly combined with footage at the end of [[Film/{{Philadelphia}} the film of the same name]].
* "Sugar Mountain". Contrary to popular belief, this song is not about drugs -- its pretty much a GrowingUpSucks song. The real Sugar Mountain was a nightclub for people ''under'' 20. 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 ''[[UnpluggedVersion MTV Unplugged]]'' album can be particularly affecting, since without the vocoder, the lyrics are naturally easier to understand.
-->''Your eyes are shining on a beam\\
Through the galaxy of love\\
Unlock the secrets, let us\\
Throw off the chains that hold you down''
** 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, [[NightmareFuel may well be hereditary]]. The most gentle, loving SanitySlippageSong you'll ever hear.
-->''[[ContinuityNod Old man]] crossing the road -- you've got to let him go.''
* "Birds". Just listen to it...
* "After the Gold Rush", a song more or less about mankind's adverse effect on the environment. Sadly, the situation has worsened considerably in multiple ways since TheSeventies.
* "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 the suicide of Music/KurtCobain. 'Nuff said.
-->''Too late - too soon - too late - too soon - [[SmashToBlack too late]]''
* Neil wrote 2006's ''Living with War'' at a time when criticizing President UsefulNotes/GeorgeWBush 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 one word'' about the pain and suffering being endured by the injured troops in the photos accompanying the article. He wrote "[[https://www.youtube.com/watch?v=dYs7QexzA4Q 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 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. Even the upbeat "Come On Baby Let's Go Downtown" is thoroughly depressing in the context of the album, since it was co-written and sung by Danny Whitten, whose death (alongside Bruce Berry's) is the subject of the entire album.
--> ''I'm singing this [[TitleDrop borrowed tune]]''
--> ''I [[SuspiciouslySimilarSong took]] from Music/{{The Rolling Stones|Band}}''
--> ''Alone in this empty room''
--> ''Too [[DrowningMySorrows wasted]] to write my own''
** "Tired Eyes" is another heartbreaker, describing a drug deal gone bad that resulted in four deaths, along with some of its aftermath. The ethereal but ragged backing vocals make it not at all less depressing.
** The [[https://hyperrust.org/General/TTNInsert.html liner notes included with the original LP]] may also qualify, as Young effectively admits he's unable to adequately articulate his grief in a manner others will comprehend. There's also a Dutch-language review of one of Young's concerts from the era, which Young has variously said he included because "I didn't understand any of it myself, and when someone is so sickened and fucked up as I was then, everything's in Dutch anyway" or because he was moved that "someone on the other end of the world exactly understood what [I] was trying to say".
--> I'm sorry. You don't know these people. This means nothing to you.
* "Only Love Can Break Your Heart" lives up to its title.
* "Cortez the Killer" from ''Zuma'' is absolutely heartbreaking, featuring thoroughly depressing lyrics and some of Young's most lyrical guitar solos ever. Alongside "Like a Hurricane" from ''American Stars 'n Bars'', it's often cited as Exhibit A for why Neil is a great guitar player.
* The intro for his album ''A Letter Home'' may sound like a typical warm message to his folks back home, but then you realize he's essentially talking to his dead mother and is basically lamenting about how unfortunate his divorced parents never made up before their deaths. To know that a divorce can cause someone psychological harm that intense, even in their elderly years, is downright heartbreaking.
* "Powderfinger", coming as it does after the acoustic side of ''Music/RustNeverSleeps'', is the musical equivalent of "the shot you never saw coming", as Allmusic critic Jason Ankeny puts it. Then the song's climax comes. ''It goes {{from bad to worse}}''.
--> ''Shelter me from the powder and the finger''
--> ''Cover me with the thought that pulled the trigger''
--> ''Just think of me as one you never figured''
--> ''Would fade away so young''
--> ''With so much left undone''
--> ''Remember me to my love; I know I'll miss her''
* "Prairie Wind" especially during a live special where he introduces the song first by talking about his father, who in his later years struggled with Alzheimer's.
-->''Trying to remember what my daddy said''
-->''Before too much time took away his head''
* Probably at least half of ''Greendale'', but especially "Carmichael", "Bringin' Down Dinner", and "Be the Rain". The former two describe [[spoiler:the aftermaths of major character deaths]] and the latter is just awe-inspiringly beautiful. The acoustic versions on ''Live at Vicar St.'' are, if anything, even ''more'' tear-inducing.
** The acoustic version of "[[https://youtu.be/JaflBpAIIxI?t=390 Bandit]]" is incredibly ethereal. At an early performance in Santa Cruz (July 23, 2003), the audience was quiet for a few seconds after he finished, then gave him a standing ovation. His response: "Thank you. I thought you'd like that."
* Neil's cover of Music/JohnLennon's "Imagine" during the "America: A Tribute to Heroes" 9/11 benefit concert in 2001, amending the line "Imagine no possessions, I wonder if you can..." to "I wonder if '''I''' can...", adding some self-doubt to the song.
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