• If I Didn't Know Better
  • The Civil Wars
  • 89 plays

Why do I keep drinking
Wasting my time on you
If I didn’t know better
But, dammit, I do…

Ever since I watched the pilot for Nashville the other day, which ends with two characters singing this song, I’ve had this on repeat (it’s playing right now and Danny just yelled from the other room, “Why are you always listening to that?”). The song has only been featured on a live album they released back in 2009, but I stumbled upon this studio recording and it’s amazing.

  • I Shall Believe
  • Sheryl Crow
  • 40 plays

Come to me now
And lay your hands over me
Even if it’s a lie
Say it will be alright
And I shall believe

Today’s sad song (yes, this is gonna be a thing now) comes from Sheryl Crow’s debut album. This one kills me because of its desperation; she’s saying: “I know everything is completely screwed up, but just tell me that things are going to be okay and I’ll believe you, all evidence to the contrary.” Gets me every time.

  • I Know
  • Fiona Apple
  • 179 plays

At my own suggestion,
I will ask no questions
While I do my thing in the background
But all the time, all the time
I’ll know, I’ll know

It’s no secret: I love sad music. There’s just something about another person being able to express — in a much more artful manner — that thing that you’re feeling/have felt. I’ve always got a song at the ready if I know anyone in need of lyrical catharsis.

Danny getting me tickets to see Fiona reminded me of this song; one of my favorites and one of her saddest (though, aside from a handful, they’re all about heartbreak). What’s so utterly gut-wrenching about this one in particular is that she paints a picture of a woman being taken for granted, each verse ending with the “I’ll know, I’ll know” of how she believes he feels about her, until the final stanza where she says: "And if it gets too late, for me to wait/For you to find you love me, and tell me so/It’s ok, dont need to say it" but doesn’t complete the verse; the song trails off. Heartbreaking.