Who Is the Saddest Girl? -The Toast

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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 QuotientOnce 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 QuotientShe 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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