Who Is the Saddest Girl?

sad

The modern male singer-songwriter has a type. She is thin. She wears a great deal of eye makeup. She is pale. She does not smile, and often walks in the rain. Most importantly, she is very, very sad. Too sad to write songs; this must be done for her, so as not to distract her from her deep and profound sadness. Often she is too sad to even have a name, so great is her sorrow. She is an indoorsy type, inclined to stay inside her bedroom, unless she is going outside to walk (in the rain) or take drugs.

This selfsame sadness causes the singer-songwriter to fall in love with the Sad Girl. He will attempt to cure her substance abuse problems/deeply troubling relational history/personal trauma through the power of song. But he cannot! This is what makes everything so sad.

Also, sometimes she has abortions, which makes him even sadder.

These Sad Girls are all terribly, terribly sad in their own unique ways, of course, but which one of them is the saddest? The Toast investigates.

Song: “The A Team”
Songwriter: Ed Sheeran
How Truly Beautiful is she?: “White lips, pale face/ Breathing in snowflakes.”
How sad is she?: “But lately her face seems/ Slowly sinking, wasting/ Crumbling like pastries/ And they scream/ The worst things in life come free to us…/And in a pipe she flies to the Motherland/ Or sells love to another man/ It’s too cold outside/ For angels to fly.”
Overall Sadness-to-Hotness Quotient: A strong contender right out of the gate. This white-lipped woman has become a sex worker and her face is turning into a croissant, but even Ed Sheeran cannot save her with his number-one hit song. Of all the pipe-smoking sex workers he cannot rescue, she is surely the palest, and the most beautiful.

Song: “Lullaby”
Songwriter: Shawn Mullins
How Truly Beautiful is she?: “Her friends tell her/ She’s so pretty/ But she’d be a whole lot prettier if she smiled once in a while/ ‘Cause even her smile looks like a frown/ She’s seen her share of devils in this angel town.”
How sad is she?: “From the stage I can tell that/ She can’t let go and she can’t relax/ And just before she hangs her head to cry/ I sing to her a lullaby.”
Overall Sadness-to-Hotness Quotient: Very high. This poor girl lives in Los Angeles, and has been forced to meet movie stars, including Sonny Bono, who is now dead.

Song: “Absolutely (Story of a Girl)”
Songwriter: Nine Days
How Truly Beautiful is she?: “This is the story of a girl/ Whose pretty face she hid from the world/ And while she looks so sad and lonely there/ I absolutely love her.”
How sad is she?: “A girl/ who cried a river and drowned the whole world.”
Overall Sadness-to-Hotness Quotient: Here we must cast doubt on the account of the men of Nine Days. How can a girl who is merely “pretty” destroy an entire world with her grief? There must be something more to the story we’re not hearing.

Song: “Brick”
Songwriter: Ben Folds Five
How Truly Beautiful is she?: UNKNOWN
How sad is she?: “Now she’s feeling more alone/ Than she ever has before/ She’s a brick and I’m drowning slowly.”
Overall Sadness-to-Hotness Quotient: Difficult to measure. At no point is it clear just how attractive or translucent this woman’s face is.

Song: “Amphetamine”
Songwriter: Everclear
How Truly Beautiful is she?: “She looks so bored sometimes/ And she has that super pale skin and those soft green eyes…/ She is perfect in that fucked up way.”
How sad is she?: “She is the saddest girl that I have ever known/ She wakes up in the middle of the night/ Just to tell me everything will be all right.”
Overall Sadness-to-Hotness Quotient: A classic Sad Girl. Her skin is pale, and she is bored (possibly due to a lack of amphetamines). She is so sad that she sometimes wakes up before the sun to tell lies.

Song: “The Freshmen”
Songwriter: The Verve Pipe
How Truly Beautiful is she?: “She, a punk who rarely ever took advice.”
How sad is she?: “Guilt-stricken, sobbing, with her head on the floor.”
Overall Sadness-to-Hotness Quotient: Difficult to say. Punks are not always beautiful. She cannot stop touching her face; this is not his fault and he will not be held responsible for it. Possible acne problem?

Song: “She Talks to Angels”
Songwriter: The Black Crowes
How Truly Beautiful is she?: “She paints her eyes as black as night now/ Pulls those shades down tight.”
How sad is she?:“She keeps a lock of hair in her pocket/ She wears a cross around her neck/ Yes, the hair is from a little boy/ And the cross is someone she has not met…/She gives a smile when the pain comes/ The pain’s gonna make everything all right.”
Overall Sadness-to-Hotness Quotient: A woman who knows how to wear black eyeliner and smiles when she is in pain is a Sad Girl indeed. “What mysterious witchcraft is this; a woman with eyes shaded black as night?” “No magic here, fellow; it is but the charm of her makeups.”

Song: “Lua”
Songwriter: Bright Eyes
How Truly Beautiful is she?: “You’re looking skinny like a model with your eyes all painted black.”
How sad is she?: “And I know you have a heavy heart/ I can feel it when we kiss/ So many men stronger than me have throw their backs out/ Trying to lift it.”
Overall Sadness-to-Hotness Quotient: Once again the male singer-songwriter is mystified by the application of eyeliner. Her heart is heavy, but her body is skinny. Very hot. Excellent work.

Song: “She Will Be Loved”
Songwriter: Maroon 5
How Truly Beautiful is she?: “Beauty queen of only eighteen…/ I want to make you feel beautiful”
How sad is she?: “She had some trouble with herself/ He was always there to help her/ She always belonged to someone else.”
Overall Sadness-to-Hotness Quotient: She is a queen, yet she is also owned by this mysterious “someone else.” She wins awards for her good looks, and yet she cannot feel beautiful without the help of at least one of the Maroons. A conundrum.

Winner: “Lullaby.” The woman can see demons and is physically incapable of turning up the corners of her mouth, no matter how many rock shows she attends.

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97 Comments

  1. anowlindaylight +19

    I woke up in the middle of the night really upset with myself that I didn’t point out 90% of the oeuvre of Jonathan Richman when Mallory asked for songs on Twitter.

  2. NicoleCliffe +55

    I literally thought the Ed Sheeran song was about Anne Frank the first four times I heard it on the radio, probably because Neutral Milk Hotel conditioned me to think sad songs are about Anne Frank.

    1. EPWordsnatcher +14

      Nicoooooooooole. You know we love you dearly, but what part of
      “Struggling to pay rent/Long nights, strange men” or “And in a pipe she flies to the Motherland/Or sells love to another man”…?

      1. NicoleCliffe +65

        I mean, I didn’t think it was a GOOD song about Anne Frank, or anything.

        1. TriannaLi +4

          Nicole, I remember you from hairpin, and I just wanted to say that rarely do I ACTUALLY laugh the way I did at a poster’s comments the way you just made me laugh (out loud and everything, even). Great article, too, Mallory who I also remember from Hairpin.

      2. urwelt +5

        To be fair, it’s difficult to understand how a lot of Aeroplane Over the Sea is about Anne Frank either. Semen stained mountaintops??

  3. safvn +44

    This delights me completely, especially this bit: “Her heart is heavy, but her body is skinny. Very hot. Excellent work.”

    I want a love song to a plump, well-adjusted woman, damnit.

    1. mamacitaconpistoles +8

      Heyyyyyyy…

      Mostly well-adjusted, plump like a dove perched on a branch.

      Very translucent skin, though, and likes snowflakes.

      Call me… we can get working on lyrics and find someone who can write music. As long as they pay us, the dude can have the byline.

    2. tkipsky +2

      No effing kidding! Why are they always anorexic and tragic and doomed? I personally find plump, rosy-cheeked, and well-adjusted women, full of vitality, very attractive.
      The Sad Girl? BOOORRRING.

      1. HariboLector +4

        I don’t know. I can’t help thinking that Big Fat Fanny the Naughty Nanny might not have been that well-adjusted; probably has some sort of psycho-sexual trauma if she’s so aggressively pursuing young teenage boys at her age.

        1. Ursula +1

          I retconned that song so that it’s about the narrator watching the naughty nanny, not being with her himself.

  4. meanchelled +32

    Here we must cast doubt on the account of the men of Nine Days. How can a girl who is merely “pretty” destroy an entire world with her grief? There must be something more to the story we’re not hearing.
    Finally, someone looking into the complex mythologies of THE BOOK OF THE MEN OF NINE DAYS. We have great need of their knowledge from the beforetimes.

    1. meanchelled +26

      Agh that sounded snarky but I am 100000% serious I also need to know how aggressively playing your super loud guitars in a girl’s face while she’s trying to read her Delia’s catalogue in 1999 is going to help her flex those smile muscles and not her screaming ones

      1. thezlot +32

        DELIA’S. CATALOGUE.

        I always thought “Absolutely” was about dude in love with a ghost. Because she looks so sad in photographs (because she exists in olden times when people don’t smile when their pictures are taken) but he loves her in the present, when she smiles ghoulishly at him and water drips, drips unceasingly from her eyeballs, ready to drown the whole world. But he loves her. He cannot help it.

        But now that I reread the lyrics, the song mostly seems to be about clothes and shoes.

  5. victorytasteslikehashbrowns +30

    I have always wondered about the amount of time the girls who are too fey too function spent perfecting their eye makeup and maybe watching youtube tutorials.

    Anyway, this is awesome! Im glad Lullaby girl won. Who are the fun girls dating?

    1. anxious_mofo +26

      TOO FEY TO FUNCTION

      as in, I am putting that on my business cards (if I ever get business cards).

    2. embryoconcepts +9

      toofeytofunction.com is available, as is toofeytofunction.tumblr.com

      Just, you know, if anyone cares.

  6. Slutface +10

    I have to stick up for Ben Folds because isn’t that song about his experience with his girlfriend getting an abortion?

        1. MalloryOrtberg +54

          Of course they are! I’m not going to arrest him and take his feelings away, I promise. Although I do kind of love that mental image.

          “Mr. Folds?”
          “Who is this?”
          “This is the police. We’ve heard reports you tried to have feelings about someone else’s abortion?”
          “I don’t know what you’re talking about.”
          “This woman got an abortion, and all of a sudden she’s a brick and you’re drowning slowly?”
          [Silence]
          “Mr. Folds, you can either come quietly or we can come in and get you.”

          Anyhow, yes, absolutely, men can have feelings about abortion, I definitely get what you mean; but it’s also more than a little ridiculous for a dude write a grandiose and self-pitying song about his girlfriend’s abortion, especially in the context of the Times We Live In.

          1. Slutface +29

            I get what you’re saying. Maybe I hear the song differently. I hear it as a guy who sees his girlfriend go through something heartwrenching and feels helpless when she becomes really depressed. I don’t hear him saying anything like “hey lady get over this” more like he knows there’s nothing he can do.

            And the song is almost twenty years old so it’s not really about Times We Live In. This song and subject matter was a pretty big deal when it came out. We spent an entire English talking about it (I was a senior in high school when it came out) and no one ever thought it was a self-pitying song.

          2. tekkah +16

            Can I just say it is really odd to me that the song is nearly 20 years old?

            Also, I agree with you that it’s just his perspective on watching his girlfriend go through a lot, it never struck me as “this is all about me.”

          3. fondue with cheddar +7

            I always heard it as a guy who wants to break up with his girlfriend but can’t because she’s so depressed about the abortion.

            They told me “Son, it’s time
            To tell the truth”
            And she broke down
            And I broke down
            Cause I was tired of lying

          4. mooniebat +6

            Wow. How is that song 20 years old? Still so relevant, still so sad. And I don’t see it as him asking for pity. More like being carried down with her by a decision they made together and were trying to hide.
            Are Tom Petty’s songs too old to get the sad pretty girl votes? American Girl is about a suicide. And Last Dance for Mary Jane, is that about a girl, or a drug? I may need to google those lyrics…

          5. lyetteann +29

            Yeah, describing one’s depressed girlfriend as a brick pulling you under is not the most empathetic metaphor.

  7. tekkah +3

    Aw, man, Brick and The Freshmen were two of my favorites when they were first coming out. And the story behind Brick is so heartwrenching. Ben Folds has spoken about how it was inspired by the experience of going with an old girlfriend to get an abortion during his live concerts (you can hear the story on Ben Folds Live).

    1. MalloryOrtberg +38

      True story: at my sixth grade birthday party (held at Discovery Zone) “The Freshman” came up on the little karaoke machine they had, and someone sang it

      and that someone was me

      1. tekkah +3

        Discovery Zone oh my god. I had forgotten that horror zone.

        I would still sing The Freshmen at karaoke, not gonna lie.

        1. Slutface +9

          You have to add Duncan Sheik’s “Barely Breathing” to this kickass karaoke playlist.

  8. jhsaxena +14

    Oooh what about the friendzone songs? I’m thinking “Flavor of the Weak” by American Hi-Fi to start.

    1. meetapossum +13

      Every song by the Ataris. “Your Boyfriend Sucks” and “San Dimas High School Football Rules” are especially notable.

        1. Faintly_Macabre +8

          “It’s like this song sounds like some highschool band made it in their garage while they were high but it still sounds great.”

          He just needs to turn that negging ability onto a girl, and he’ll be off to a great start!

    2. Abanthis +3

      Sherwood’s whole oeuvre is magnificently passive-aggressive, but “Middle of the Night” is among the worst.

      1. anxious_mofo +12

        damn, “Jessie’s Girl” is like PUAs’ anthem. “I been funny, I been cool with the lines/ain’t that the way love’s supposed to be?” Yeah dude, why are your lines not working? What’s that guy got that you don’t got? Why can’t you find a woman like that? You’re a Nice Guy!

  9. WibblyWobbly +30

    A girl…who cried a river and drowned the whole world has always annoyed me so much, especially when he says “I absolutely love her when she smiles“. Like, oh I’m so glad that you can find something to love about this poor sad girl, because what would femalekind ever do if you couldn’t…?!? Come on.

  10. serenityfails +6

    I humbly submit Sugarcult’s “Pretty Girl”. You see, it is sad, because /she/ is sad, and she is also pretty.

    1. Abanthis +8

      And yet there is nothing more to her than being pretty, sad, and liking/being liked by guys. That kind of thing is what icks me out about “Code Monkey” even though all my guy friends adore JoCo.

  11. anachronistique +27

    “at least one of the Maroons”

    I think I drew blood in my lip-biting efforts to not openly cackle in the office.

  12. moved to comment +12

    not a new trend! i humbly submit “sad lisa” from “tea for the tillerman” (1970):

    Her eyes like windows, trickle in rain
    Upon the pain getting deeper.
    Though my love wants to relieve her.
    She walks alone from wall to wall.
    Lost in her hall, she can’t hear me.
    Though I know she likes to be near me.

    Lisa Lisa, sad Lisa Lisa.

    1. Bunni +5

      That’s the point where I lose it, every time I hear that song. I’m willing to play along with their sad-song game until they say that line, then I’m just “Mmmmm, pastries. Gonna get some.”

      1. meetapossum +4

        The first stanza is. But I always thought Anna Malick seemed more upset about that than the girl getting one. The second stanza is:

        May he turned 21 on the base of Fort Bliss
        Just today he sat down to the flask in his fist
        Ain’t been sober since maybe October of last year
        Here in town you can tell he’s been down for while
        But my God it’s so beautiful when the boy smiles
        Wanna hold him but maybe I’ll just sing about it

        1. practical cat +3

          Yeah, I thought that was about the father or whatever. But I suppose it could be about a completely unrelated incident.

          I mean, he’s definitely the Sad character in the song, for sure.

  13. tekkah +9

    Ben Folds has a couple of others, too: Losing Lisa and Carrying Cathy are both about sad girls. Cathy climbs out a window and kills herself and Lisa’s crying “black tears” and won’t tell him what he’s done. I’d go ahead and say I think Carrying Cathy is Ben’s saddest sad girls song.

  14. deleted4899619 +34

    “Oh yes, pretty, pretty little dolls, but sooo sad. So pretty and sad. And that makes me, a man, sad because why is my pretty, pretty little doll so sad? Doesn’t she know how pretty she is? I’m gonna write a song and tell her. Cause she is my pretty, pretty little doll. Hehe, so pretty! Smile, pretty doll! Why so saaaaaaad?!”

    1. deleted4899619 +46

      It just seems like these guys are so baffled as to why a pretty girl would be sad, when she’s pretty, aka the highest achievement any woman can reach. Maybe she’s sad because no one takes her work in physics seriously because she’s so pretty.

      1. Linette +26

        Whenever pretty girls feel sad, they should just go out and have sex. Sex will cheer them up. I, a musician, will nobly volunteer for this cheering endeavor.

  15. DiaphanousGown +6

    What, no “where do you go to my lovely”? She wears Balmain, has diamonds and pearls in her hair, lives in a fancy apartment. Her loveliness goes on and on! BUT she still bears the scars deep inside of being a homeless, rag-wearing beggar child.

  16. Linette +28

    Is this the place to talk about why I hate the One Direction song Beautiful? Because it’s super catchy and all in that poppy way, and yet –

    “You don’t know you’re beautiful
    THAT’S WHAT MAKES YOU BEAUTIFUL” – I can’t even, you guys. I’m only beautiful if I’m totally insecure and incapable of acknowledging my attractive features. No, to be properly beautiful I have to be good looking AND hate myself.

    1. EPWordsnatcher +12

      Stephen Colbert did a magnificent take-down of this song that ended up with him coining the term “Mobius Pop.” Worth looking up.

    2. oneforthebyrds +4

      YES!!!

      Every time I hear this song, I think of that. And then I change stations.

  17. EPWordsnatcher +23

    Why are we not talking about The Wallflowers’ “One Headlight”?
    “It always seemed such a waste/she always had a pretty face/I wondered why she hung around this place [a cemetery]” AND she “died easy of a broken heart disease.” SAD/PRETTY.

    1. FlufferNutter +8

      I am missing the presence of the Counting Crows here, too. Pretty much any song from August and Everything After is a contender. “She says ‘it’s only in my head’/ She says ‘Shhhhh I know, I know it’s only in my head.'”

  18. QueenElisatits +14

    The worst thing about the songs is how much teenage girls internalize the message about being sad and helpless is sooo hot and will get you all the boys. Never worked out but damned if I didn’t wish I could be waify and sad. I’m not alone here right?

    1. Linette +19

      Depends on which songs you take to heart. I was under the impression that if I was a stone-cold badass who shot down the boys all the time, they would all want me. This actually proved to be fairly accurate, but the damn songs never explain how to transition from that status quo into any kind of actual relationship, so it made for a decade of problems.

    2. SeaVineyard +11

      Not alone! I so desperately wanted to be a sad waif but could not have been any less of a waif. I had the sad part down but understood that my non-waifness would never allow me to be a girl in one of those songs, though I’d be damned if I didn’t try. I really really internalized those songs, and your comment + watching Reality Bites on the cable last night made me realize how much so. I wanted to BE Winona Ryder SO BAD and be small and pale and dark-eyed gorgeous in oversized thrift store clothes that highlighted my waifish appeal, and the memory of that desire makes me so sad, not just for the misguided fashion sense (i just looked bad in oversized thrift store jeans, not appealingly rescuable) and the real feeling that I’d never be loved because I didn’t fit that mold.

      1. Linette +15

        It is a hard day when you realize a “look” that you admire and covet belongs to a body type that is not your own.

        Acknowledged: it is even harder when if all the looks you’ve ever seen belong to body types that are not your own.

        1. anninyn +10

          Yes. I want to be cool and elegantly androgynous. Sadly I have big breasts, hair that will never do as I tell it, a little round face and I go pink really easily. Also I witter. It is an unattainable dream.

  19. thezlot +19

    This post reminds me of Bill Bailey’s Chris deBurgh parody, “Beautiful Ladies.” “I will protect them / I will save the pretty ones / With their smiles, and their sparkling eyes / But let the ugly ones die / I have no place for them in my new world order.”

    “It is but the charm of her makeups” is obviously something we all need to start saying.

    1. 1sic1 +6

      ‘I won’t waste my seed on hideous trolls
      Kill, kill, kill, kill, kill the trolls
      Hunt them down, there shall be no clemency
      Kill, kill, kill, kill, kill the trolls
      Look under the bridges, that’s where they hide…
      And beauty shall be my bride”.

      Oh, Bill…

    2. Faintly_Macabre +4

      That is wonderful, thank you!

      “Beautiful ladies are lovely, but sometimes they don’t take care, they’re too busy with their makeup, or combing their lovely hair….to take basic safety precautions.”

      Here’s a link, for anyone lazy

  20. lyetteann +64

    I just realized that, 20 years after the fact, I still think of the girlfriend in “Brick” as bald because the first few hundred times I misheard “balled up on the couch” as “bald upon the couch.”

    Poor, sad, bald, abortion-having girlfriend.

  21. depizan +7

    What about Ne-Yo’s Let Me Love You? It doesn’t say how beautiful she is but:

    Much as you blame yourself, you can’t be blamed for the way that you feel
    Had no example of a love that was even remotely real
    How can you understand something that you never had?
    Ooh, baby, if you let me, I can help you out with all of that

    Girl let me love you
    And I will love you
    Until you learn to love yourself

    1. EPWordsnatcher +8

      UGH yes.
      Similarly, that horrific One Direction song “Little Things”

      “You’ll never love yourself
      Half as much as I love you
      You’ll never treat yourself right darlin’
      But I want you to
      If I let you know
      I’m here for you”

      This after talking about how he will still love her even though she has to squeeze into her jeans. MAGNANIMOUS.

  22. mayamia +1

    The Lua song by bright eyes is actually about her eating disorder and drug addiction that he shares the song also recognizes that he can’t help her and almost doesn’t want to
    “But me, I’m not a gamble, you can count on me to split
    The love I sell you in the evening, by the morning won’t exist”

    1. aekessler +5

      Oh God. That song. It’s just so ridiculous. Yes, you go ahead and work out in your high heels. That isn’t an accident waiting to happen.

  23. amitygardens

    Oh God. That song. It's just so ridiculous. Yes, you go ahead and work out in your high heels. That isn't an accident waiting to happen.

  24. Lolo +3

    At least the Lua girl is only skinny because she has a coke problem, not because of healthy diet and exercise!

  25. Amanda +1

    Someone mentioned it, but “‘Round Here” needs to be considered. Also, they might not fit exactly, but “Cath” by Death Cab for Cutie and “Allyson” by Elvis Costello are lovely pieces of men patronizing foolish women. I hate Elvis Costello because of that song. He just sounds like such a dick.

  26. Joan Defers +1

    That Ne-Yo song girl so owns this. She’s so sad that even his perky trance anthem bullshit and epic dance moves can’t cheer her up.

  27. Da va

    I always understood The Freshman as being from the vantage of a guy whose ex-girlfriend took her life, it’s “I’m guilt stricken” not “she’s guilt striken.” Also, Nirvana’s Polly seems to be sung from the perspective of an abductor rapist or seriel killer.