Playlist of the Month: Soundtrack to my Tears

It’s been an (ironically) fun week for us, talking about crying and feels and emotions, and where and when and what makes us break down. On the final day of A Cry For Help Week, we’re sharing some of the songs that are trigger tracks, if you will. The songs that either will make us cry when we hear them or if we’re in dire need to let it out, we listen to these tunes to set off a flood of tears. I think everyone needs a go-to list of these kinds of songs, so hopefully this will help you if you don’t have one already! And if you do have these songs in your arsenal, feel free to share your own Soundtrack To Your Tears.

Listen to the entire playlist on Spotify!

Molly’s Picks

 Ben Harper – Walk Away

This is the rare breakup song that works if you are the dumper or the dumpee – either you have to walk away because you’re the one calling it quits, or because eventually you have to move on. Either way, now you’re crying while listening to Ben Harper.

Elliott Smith – Between The Bars

You can’t have a crying soundtrack without a little Elliott Smith.  Even happy-ish Smith songs can make me weepy (see, e.g, Say Yes). Between The Bars is like a song from the ugly part of your brain – minus, for me at least, the parts about problem drinking. But the mean narrator in your head has probably said a thing or two about “the things you could do, you won’t but you might” and “the people you’ve been before that you don’t want around anymore.”

Crosby Stills Nash and Young – Our House

This is my wild card pick. Ever since I was a baby who wept every time I heard Hush, Little Baby, unlikely songs have made me cry. My mom thought I hated that lullaby because everything broke, but I could have cared less about the baby from the song and her conspicuous consumption. The melody was just a real downer. For as long as I can remember, I’ve also found Our House to be a bummer. Part is the melody, and part of it is that I was a kid with a really vivid imagination and I’d always picture a young, happy couple from the 1970s hanging up their macrame and tapestries, and I’d know that by now those days are long gone.

Lisa Hannigan – Lille

If you couldn’t tell from Our House, one of the most tear-inducing feelings for me is thinking about how quickly young people become old people and how in the end it’s all just sort of … okay. It’s a happy-sad feeling, like looking at your grandparents’ wedding pictures.

Neutral Milk Hotel – Holland 1945

This song neatly summarizes my theme of “when people live then die then become part of the past, it’s beautiful yet sad.” I mean, it’s from Neutral Milk Hotel’s Anne Frank-themed album. Why do I do this to myself again?


Lua by Bright Eyes;  re: Stacks by Bon Iver; Casmir Pulaski Day by Sufjan Stevens; Marshmallow Unicorn by Rachel Sermanni, … do you want me to keep going? Because I can keep going.

Traci’s Picks

The Last Five Years – The Next Ten Minutes

So, since we’re all friends here, I’m not ashamed to say that I lit’rally have a playlist on my iTunes called “Cry It Out”, featuring songs that I listen to when I want to cry. Pretty much the entire soundtrack to one of my favorite musicals, The Last Five Years, is on said playlist. If you’re not a theater nerd, The Last Five Years is a musical that was off-Broadway in 2002, and has since become a cult favorite. In fact it had an off-Broadway revival last year and next year, you will see me at the movie theater crying into a bucket of popcorn by myself because the movie adaptation, starring Jeremy Jordan and Anna Kendrick, hits theaters. In short, The Last Five Years tells the story of Jamie and Cathy over the last five years (duh) of their relationship. Jamie tells the story of their love in chronological order (starting when the couple first meets), while Cathy tells it in reverse (starting when their marriage ends). There is one song in the show where their timelines intersect, which is their “wedding” song, and that is this one, titled The Next Ten Minutes. Since this is the only song where they’re on “the same page”, we get a rare glimpse of the romance between them, and it’s even more devastating knowing how it’s going to end.

Once the Musical – Leave

I’m telling you right now, there’s one more song from a musical after this, so scroll if you must. I started listening to the Once soundtrack when the Broadway show was gaining popularity and winning awards and all that, but it wasn’t until a few months ago that I actually saw the production for the first time. I laughed, I cried, I went another time and lather rinse repeat. This soundtrack is also on my Cry It Out playlist, and Leave is just one of the great tunes off the soundtrack. It’s the first the Guy sings in the show, and sets up a tale of unrequited love that shatters your heart to bits.

Rent – I’ll Cover You (Reprise)

(Last musical song, I promise) I feel like Rent is such a cliche show to say is your favorite, but it pretty much is. It’s the show I’ve seen live the most (like more than 8 times?), and that’s partly because I first saw a touring production of it while in high school, and it comes with sentimental memories for me. Anyways, at the climax of the show, *spoiler alert* Angel dies, and Collins mourns the loss of another AIDS stricken friend gone too soon. Jesse L. Martin does such a good job at expressing the anguish, pain and suffering through every single note in this song, and the fact that it’s a reprise of a song he sings with Angel in the first act, digs that knife in even deeper.

Carrie Underwood – So Small

I mentioned earlier in the week that Carrie Underwood will make me cry no matter what. I think it started when she won American Idol and could barely get through the final song because of her tears of joy. From that moment, anytime I hear her live, it’s guaranteed I will at least tear up. I mean I even found myself crying when she sang her new song at the CMA Awards on Wednesday (to which I reminded myself to write about it for this post). So Small is just one of the tear-inducing tracks, and in the video above, she sings it with our fave the PS22 Chorus. With a kid chorus behind her, the song takes on a whole new level, and I think it’s exactly what Carrie wanted.

The Civil Wars – Poison & Wine

This makes me sad before even listening to it because I mean, RIP The Civil Wars. Joy and John Paul’s haunting harmonies were their signature sound, and it’s prominent in one of their most popular songs, Poison & Wine. Their music was unlike any other act today, and I’m not sure if I’m crying because of the song itself or knowing that we’ll never hear new music from them again.

Adele – I Can’t Make You Love Me / Make You Feel My Love

Of course Adele is on this list. Her music is a sure fire way to let it all go. When SNL does a sketch about how your music makes everyone cry, you know it’s true. And while it’s like Sophie’s Choice picking one Adele song that makes me cry, I decided to go with a song that basically makes me cry anytime I hear it, which is I Can’t Make You Love Me originally by Bonnie Raitt. So combine that track with Adele and you have emotion central.


Ugh so many songs, it was really hard to narrow down, but here are two that came real close to making the top 6!

Demi Lovato’s cover of Ed Sheeran’s Give Me Love: Like all songs Demi sings, she puts so much power in it, but you can tell she’s signing this from personal experience, and I get the chills every time I listen to it.

Brett Dennen’s version of Hard Times (Come Again No More): This song came to my attention via Parenthood, so obviously it makes me cry.


5 thoughts on “Playlist of the Month: Soundtrack to my Tears

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