We all have them; those songs that you listen to when you’re down in the dumps and all you want is to to cry some more. You know, the ones that make you feel like you’re in the montage of a movie that may or may not also star Joseph Gordon-Levitt. Or the scene immediately following the montage, since that one usually holds some kind of epiphany or dialogue that speaks to your situation. Don’t you dare try to cheer me up, I’m on a mission! Whether it’s because of the melancholy lyrics, somber minor chords, or sad, sultry vocals, you count on these songs to keep you marinating in your sorrow. They vary from person to person, so in honor of this cold and rainy New York morning we each picked one of our personal favorite songs for a world-class sob-a-thon.
*Disclaimer: It’s probably the hardest thing we’ve ever had to do to each only choose one song. Our most sincere apologies to the other songs in our sad-day playlists and YouTube compilations.
Sandy Rooney
Lauryn Hill, EX-FACTOR listen
From The Miseducation of Lauryn Hill, 1998
We’re all familiar with what it feels like to miss somebody, and when you’re sad and alone and want to wallow, sometimes it’s best to find a girl with more soul than you’ll ever have who can put into words how lonely it is to want someone who doesn’t want you, who gets under your skin, who messes with you for fun. This song, a letter to an ex-, carefully traverses the sadness terrain by placing blame in two places: on ex-, and on self. Talk about wallowing! “As painful as this thing has been, I just can’t be with no one else. See, I know what we’ve got to do: you let go, and I’ll let go too.” There is no feeling more sad or helpless than placing control in the hands of someone whom you don’t trust at all not to hurt you. To me, the song is as raw as the big fight and as despondent as the morning after. “You said you’d die for me.” Brutal. Thanks for ripping my heart out, Lauryn! I can’t imagine what you did to the guy this is for.
Shady Satin Drug
Broken Social Scene, ANTHEMS FOR A SEVENTEEN YEAR OLD GIRL listen
From You Forgot It In People, 2002
When I was in high school (and still now) I had a huge thing for people who were a little broken. Not crazy, killing animals in the woods broken, just people who were quirky to the point that they were off-putting to other people. The ones who were a little too obnoxious, neurotic, pedantic, emotional, detached or quiet for other people to want to really get to know. This wasn’t something I was forthcoming with; I just tended to quietly admire these people and their style from afar. So when I first heard this song by Broken Social Scene, it cut right through me. It repeats the same lament over and over “Used to be one of the rotten ones and I liked you for that.” It perfectly captured the quiet heartbreak and resentment seventeen year old me would feel when I would see one of my secret admirations changing into something else. Regardless of what the song’s truly about, Emily Haines soft whisper of a voice and the sparse instrumentals of the song are perfect for cozying up in bed with a bag of your favorite candy and letting your feelings wash over you.
Antigone on a Hot Tin Roof
Death Cab for Cutie, TINY VESSELS listen
From Transatlanticism, 2003
Sometimes relationships don’t end with a bang – they go out with the whimper of no strong emotion at all. The titular “tiny vessels” that “ooze into your neck” are more or less an afterthought, “form[ing] bruises that you said you didn’t want to fade” – one of many little lies the couple told one another over the course of the relationship. There are some harsh words (“vile”, “cheap”) before the end, but Ben Gibbard saves the nastiest for last. “You are beautiful”, he admits, “but you don’t mean a thing to me.” The complete devastation that line delivers to any girl’s “honesty” sweet spot (we say “just tell me the truth”, but don’t always want to know) lingers as the song’s soft melody pulls us further from the point of impact, until we find ourselves in the vast ocean of the next track, wondering why it couldn’t be us the singer needed so much closer.
The Pumpkin
Less Than Jake, GOODBYE IN GASOLINE listen
From B is for B-Sides, 2004
If you are in the right mood and/or capable of wallowing to a frantic up-tempo ska/punk song, Less Than Jake’s “Goodbye in Gasoline” can be devastating. It’s designed for those times when you’re wide awake at the wrong end of the morning, wondering if anyone’s ever felt the way you do at that moment: cold, lonely, and like an utter failure as a human being. This song is both a comfort and a dose of salt in the wound, because it makes you feel less alone (the voice of lead singer Chris Demakes, ravaged by alcohol and cigarettes, has enough passion and bitterness to make you really believe he’s been there too) while suggesting that there might be no real solution. It’s about reaching the point where you can’t think of doing anything but escaping, just getting in a car and driving until you don’t recognize anything around you. Who’s up for a weepy, angry 3am solo road trip?
Le Chocolat Nonpareil
U2, WITH OR WITHOUT YOU listen
From The Joshua Tree, 1987
You just broke up with your boyfriend. You didn’t want to – you still love him – but the fact is that it wasn’t going anywhere. But as you drive away from his place you feel like your heart is breaking in half. You’ve forgotten how to not be with him. Your heart breaks every time you realize you can’t text him about little things like the biker you just saw collide with a skateboarder. Things weren’t great with him, but they suck without him. That’s where Bono comes in. The keening treble of The Edge’s guitar as he floats over the intro. The resignation in Bono’s voice as he comes to the realization that he can’t be in this toxic relationship but he can’t be out of it either. A tear drips down your face as he grits out “I can’t live with or without you.” You’re choking up as you try to sing along with “And you give yourself away” because you did! You gave him everything and now what do you have? By the time the singalong part in the bridge comes along, you’re full-on sobbing as you drive down the freeway. You don’t even care that people are judging you. Because Bono understands. And that’s all that matters right now.
Junie Cleaver
GOODBYE UNTIL TOMORROW/ I COULD NEVER RESCUE YOU listen
From The Last Five Years, 2001
This song is uber depressing but starts out all chipper and upbeat. It is from a 2 person musical about their 5 year relationship/marriage. What makes the show interesting is that the female character (Cathy) starts the show at the end of their relationship while the male character (Jamie) starts at the beginning. The only time they are singing together is in the middle when they are at the same place in their relationship. So effing deep RIGHT?! So “Goodbye Until Tomorrow” is the last song and Cathy is now at the beginning of their relationship and is singing a cute song about saying goodbye at the end of their first date, but Jamie is singing this tragic song about how he is saying goodbye forever. The contrast KILLS me. The line that gets me every time is Jamie singing “I could never rescue you/all you ever wanted/ but I could never rescue you/ no matter how I tried/ all I could do was love you/ God I loved you so” It just makes me cry. A lot. His sweet sweet loving voice and her sweet sweet optimism when you KNOW how it’s all gonna end. [Sigh] Musicals are not all jazz squares and top hats ya know.
Sparkles Glitterati
Lykke Li, I KNOW PLACES listen
From I Follow Rivers, 2011
“I Know Places” by Lykke Li. The emotion of this song hits you instantly – the second the music starts. And it seems that regardless of what you may be experiencing in life, everyone has a desire to escape, to get away to a place where they feel safe. We all know that the things we use to medicate ourselves in tough times eventually wear off, and we are left staring those problems right in the face. For me, this song is a story of a girl telling a man that he can finally escape, finally get away from the pain, and find solace with her. It touches me because at times I’ve felt like I was that girl, and other times that I needed a person like that. Lykke li’s voice is soft yet haunting, this song is hypnotic, in a way that almost helps to begin you on your journey to where ever that place may be.
Seven Bedroom Suite 