I have always had a soft spot for weepy stuff. There are certain movies that make me cry every time I watch them. I have even been known to choke up at a few key scenes in “Game of Thrones.” I am, in the words of carnival barkers, easy marks. A softy. A wuss.

This is a mantle I carry proudly. I feel like it proves either that my humanity is intact, or that I maybe need to up my meds a bit. But either way, I’m not ashamed of it, and when you can have a good cry with someone over a shared experience, it deepens the bond between you, sort of like finding out that you and the other person both go to the same whorehouse.

Songs have a much harder job than movies in getting this response out of me, because they only have a couple of minutes to do it with. It also lacks the visual element, establishes no characters and can’t manipulate you with cheap plot devices. So, a song that can really get you worked up in just a couple of minutes, in the same way that a two-hour movie does, is like a free-standing, three-minute work of art.

Here’s a list of 10 songs that do it to me every time. Get out your hankies before you proceed.

PJ Harvey – “Who Will Love Me Now?”

The title says it all. Between the abandonment-centric lyrics and the arrangement in D minor, which Nigel Tufnel called the saddest of all keys, this song perfectly encapsulates the feeling you get when you come home and half the furniture is gone.

Townes Van Zandt – “Nothin’”

It was hard to find one Townes Van Zandt song for this list, because about 90% of his material wallows in abject misery. This one is probably the most consistently miserable, right down to the last lines of the lyrics.

Low – “Will the Night”

The lyrics to this song don’t really say much, since Low is infected by the same refusal to write situation-specific lyrics as so many other 90s indie bands. They more than make up for it with the music though.

Queen – “Who Wants to Live Forever?”

The 1980s were not the best period for the music of Queen, when they turned their backs on rock to a certain degree and tried to keep up with new wave. Still they could turn in the occasional masterpiece when they wanted to, and given this song’s 1986 vintage, it’s hard not to wonder if Freddie Mercury, who would die five years later from AIDS, didn’t have a slightly autobiographical hand in the lyrics.

Roxy Music – “A Song for Europe”

The arrangement to this song is expertly stylized, and it’s entirely possible to imagine yourself in some Parisian café, having this song warbled to you by a drunken and near-death Edith Piaf, as you imbibe glass after glass of cabernet to wash away the horrible memories.

Dolly Parton – “The Bargain Store”

Dolly Parton doesn’t get nearly enough credit for her exemplary work as a songwriter. “The Bargain Store” is no exception, and it perfectly captures the feeling of being used, abused and cast aside.

Gillian Welch – “Leaving Train”

This is another song where the real sadness is less of a product of the lyrics and more about the music and arrangement. Gillian Welch has never been shy about using stark arrangements, and it serves her well here.

Buffalo Springfield – “Expecting to Fly”

Neil Young has been instrumental in writing countless weepers, but this song, from his days in Buffalo Springfield early in his career, is tough to beat. On a personal note, I also associate it with a time in my life when I was completely miserable, so it has that going for it too.

Nick Drake – “I Was Made to Love Magic”

Nick Drake committed suicide at an early age, so anything he wrote sounds pretty tragic in retrospect, whether he meant it to be or not. This song, on the other hand, is impossible to interpret as anything but completely sincere in its effort to evoke moans of despair from anyone in earshot.

Tom Waits – “Martha”

If Tom Waits knows how to do anything, it’s how to evoke feelings of regret over times long gone and beyond reach. This song in particular perfectly captures the feeling of having moved on to a great new place in life, of being happy, of being well beyond the bad times… and meaning none of it.

If you enjoyed this, check out some other great stuff on The Z Review

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About Author

Daniel Bukszpan is a freelance writer with over 20 years' experience. He has written for such publications as Fortune, CNBC and The Daily Beast. He is the author of “The Encyclopedia of Heavy Metal,” published in 2003 by Barnes and Noble and “The Encyclopedia of New Wave,” published in 2012 by Sterling Publishing.


  1. His Majesty O'Keefe on

    The Way by Fast Ball a sad true story, the songwriter predicted the ending before it was known

  2. His Majest O'Keefe on

    The Way by Fast Ball a sad true story, the songwriter predicted the ending before it was known

  3. “REAL EMOTIONAL GIRL” randy newman
    “HERE IT IS” leonard cohen
    “THE JUNGLE LINE” joni mitchell (best version by l.cohen & h. hancock)
    “FACTORY GIRL sinead o’connor & the chieftains
    “TIL I DIE” beach boys
    “THE PRICE OF THE BOTTLE” louvin bros.
    “VISIONS OF JOHANNA” bob dylan
    “RIVER ROAD” jimmy lafave
    “CRY ME A RIVER” etta james

  4. agree with the George Jones mention above…. to me, saddest of all time is “Sam Stone” by John Prine

  5. Patrick Anthony Lynch on

    Quite a poor list (other than T. Waits); I might even include another one by him.
    And I could pick much sadder songs by Roxy Music / Bryan Ferry.
    So putting my money where my mouth is, let me suggest:
    Many to choose from June Tabor (ex. ‘The Fiddler’)
    ‘Alison’ by Elvis Costello (the sadness is mainly in the lyrics)
    ‘I want none of this’ by Radiohead
    ‘Sorry Seems to be the Saddest Word’ by Elton John
    ‘Daniel’ by same
    ‘Sweetheart Like You’ by Bob Dylan
    Something by Van Morrison or Leonard Cohen
    [Of course, the saddest songs of all are from trad music generally (Ireland, England, Norway, etc. etc.) and from the ‘classical’ realm]

    • While it is near impossible to get a definitive list, I would say this is not even Tom Waits saddest song. Georgia Lee from Mule Variations rips my heart out.

  6. ArtHouseforOurHouse on

    Holland, 1945 – NMH
    Sadly Beautiful – Replacements
    It Makes No Difference – The Band
    Over Your Shoulder – Dinosaur Jr. Although you can hear J giggle at the end

  7. Queen in the 80’s were BADASS! Hammer to Fall, One Vision, Another One Bites The Dust, Flash…..

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