Cry Myself to Sleep:

Saddest Songs Ever Written

By Anthony Ken

Something about the cool breeze that comes along with the ‘Ber months that make us single people even lonelier. For what brutal reminder can there be that we are alone than having no one to warm us during these cold nights? Huhubels.

We tend to become masochistic about our single status and have the natural inclination to feed our melancholy. So, to make us feel even more despondent, we scoured the ‘net for the saddest songs ever written about love. Kapit mga besh.

8. Wiseup- Aimee Mann

It’s not what you thought when you first began it
You got what you want, now you can hardly stand it

Featured in Paul Thomas Anderson’s masterpiece Magnolia, Aimee Mann wrote Wiseup originally for Cameron Crowe’s Jerry Maguire. Anderson liked the song so much, his film Magnolia was written around it. At some point in the film, all the cast members take their turn in singing the song.

Mann sings “it’s not going to stop” over and over again. We get it Aimee. We get it.

7. Shelter-Ray LaMontagne

You tried to stay, but could not stand it
To see me shut down slow
As if it was the easiest thing to do

Released in 2004 via the album Trouble, singer-songwriter LaMontagne’s raspy vocals on this song cut straight to our broken hearts. It squirms its way in there and wreaks havoc. And we let it, because it makes a beautiful sound.

6. Slow Dancing in a Burning Room-John Mayer

This is the deep and dying breath
Of this love that we’ve been working on

Mayer, outspoken modern-day guitar god, hits us squarely on the gut with this slow-scorcher. The song starts off lazily, then builds up to a firing crescendo by the song’s outro. Ugh, hurts so good.

5. Ashes and Wine- A Fine Frenzy

Is there a chance
A fragment of light at the end of the tunnel
A reason to fight?

Before she turned to acting (starring in Parenthood as Kaya), Alison Sudol was known as A Fine Frenzy. Listen to that string section. That alone makes me want to cry. Then Sudol delivers the deadly combo of haunting vocals and ramdam-sa-buto painful lyrics. By the time the chorus comes back for the finale, we’re already down for the count.

Pages: 1 2