While I Cry by The Monkees
A breakup song to rival any other, this Michael Nesmith-penned piece explores the fact that the protagonist was warned about the female antagonist ahead of time, but was so blinded by love that he just stumbled on.
Here I Sit by The Ronettes
Yet again, a forewarned protagonist looks back on a lost love they should have known better about. Plus there's that extra part where it was co-written by Harry Nilsson based on a dirty bathroom graffiti joke.
Keep Breathing by Ingrid Michaelson
Ingrid Michaelson sings of the intense pain of lost love that allows you only to "keep breathing."
Woke Up New by The Mountain Goats
The poetry John Darnielle brings to a piece is so perfect in this song, and for these emotions, that even if you haven't lost love, you can feel it.
Black Coffee in Bed by Squeeze
The memories, "the hurt and the anger and the joy and the pain" are all discussed in this tale of a former love.
One by Harry Nilsson
Made famous by Three Dog Night, this song, written by Harry Nilsson, represents a cross-section of the late songwriter's interests; sad love songs and numbers. Plus if you're part of my generation, you might remember this song from the episode of "Even Stevens" in which Ren loses her stuffed monkey.
Thank You For Breaking My Heart by Ben Folds Five
One of the most tear-jerking songs on the list, yet it has a somewhat uplifting message "thank you for breaking my heart//now I know that it's in there." Alright, so not very uplifting, but it reminds us that each broken heart just helps us realize we still have a heart to break (just like the Tin Man!).
The End of the World by Herman's Hermits
In a soft and beautiful way, Peter Noone delivers this Arthur Kent and Sylvia Dee tune about thinking lost love is the end of the world (just a reminder, it's not).
Photograph by Ringo Starr
If you watch the Concert For George rendition of this song, you will cry your eyes out. Even as a single though, this song is a winner in the category of being sad (unless Morrissey is in the mix, but that's another topic).
She by The Monkees
One of my favorite things about The Monkees is the fact that this song is completely different from the other Monkees tune on this list. Different musical era, different genre and style, and even a different attitude to betrayal and loss.
Last of Days by A Fine Frenzy
A similar premise to "Keep Breathing," this song theorizes that the narrator will be lost without their beloved. I hope they came to their senses.
Walking on Broken Glass by Annie Lennox
Had this playlist been a little less mopey, I would have included The Eurythmics' "Thorn in My Side" instead, but that seemed a little too positive amongst the rest of the songs.
Love is a Bourgeois Construct by Pet Shop Boys
My favorite thing about this song is that the narrator has totally not learned that "Love is a Bourgeois Construct," that's just the view he's pretending to hold, though he still expects his lover and relationship with love return ("so I'm giving up the bourgeoisie//until you come back to me").
Now I'm All Messed Up by Tegan & Sara
Out of all of these songs, this is the one that perfectly captures a feeling in the pit of your stomach, imagining your former lover with someone else.
Any More? I'd love to hear them.
And if you live in the area of Marion, Ohio, be sure to catch most of this playlist Thursday night at 7 on One-Mind Tracks on 97.5 WDIF.