“River, oh river, river running deep. Bring me something that will let me get to sleep. In the washing of the water, will you take it all away? Bring me something to take this pain away…” -Peter Gabriel, “Washing of the Water”
There are three kinds of people in the world: 1) People who cry about their own lives, 2) people who cry at music and other entertainment, and 3) people who refuse to cry. I generally fall into the second category. I tend to cry more over songs and TV series than I do about my own life and have already written about TV scenes that make me cry. Music, especially, can make me cry when I need it most. Sometimes when I want to cry about things in my life, I can’t do it until a song triggers it. We’ve all been there, right? Some people like to listen to happy music when they’re sad, but I’ve always been the opposite. Happy music when I’m sad just makes me more aware of what I’m missing out on; sad songs make me feel better because I feel less alone, and they can give me that release I need.
Of course, there are some happy songs that can make you cry, too. But 99% of the time, it’s the sad one that make us cry. As someone with a playlist for everything, I have certain go-to songs whenever I need a good cry and the playlist to match, appropriately titled Cry Your Eyes Out. While I could just tell you to read This Will End in Tears: The Miserablist Guide to Music, an actual book about tearjerkers, what fun would that be? Do you really expect me to let you find your own suffering, stuck in a world with cliché Adele songs? Don’t be silly…
This is far from an exhaustive list, even though I narrowed it down to 20, and I left some off specifically because I intend to use them in future lists. However, it is essentially the ones that pretty much always make me cry, without fail. Some are ones everyone knows; others you’ve likely never heard unless you’ve had a Who Can Make The Other Person Cry First Using Only A Song? contest with me. (It’s a thing.) Some are easy to understand; others I can’t really describe why they have the effect they do. Because of the mood of the playlist, these are mostly all pretty sad. This is your warning. I’m not guaranteeing any or all of these songs will make you cry, just that they work for me.
The usual rule applies: One per artist, even if they’ve had more than one band. This is mainly so I won’t just have 20 Luke Sital-Singh songs to leave you crying forever. I may live to make you cry, but I’m not that cruel. That’s more than I can say for Luke ‘Magical Misery Tour’ (his words, not mine) Sital-Singh, who makes a living making me cry.
They are also, of course, (mostly) in no particular order because you can’t exactly rate the number of tears a song causes you cry. Get your tissues ready…
Honourable mentions: “Overcome By Happiness” by Pernice Brothers; “Hangman” by Paloalto; “Here Comes the Flood” by Peter Gabriel; “Almost Lover” by A Fine Frenzy; “Hallelujah” by Imogen Heap (only this version); “Somehow” by Evan and Jaron; “Not As We” by Alanis Morissette; “Quicksand” by David Bowie… Okay, there are so many, and this is getting long already, so I’ll just add ‘almost every Luke Sital-Singh song.’
20. “Bullet Proof… I Wish I Was” by Radiohead
What list of depressing songs would be complete without the crushing music of Thom Yorke? As any Radiohead fan knows, there are many songs that could have made this list, but this is one of my favourite Radiohead songs. Everyone knows it, so I don’t think I need to say any more.
19. “Dying” by Five For Fighting
Say what you will about Five For Fighting, but this song helped me through heartache in my early university years and continues to help. “I’m dying, dying to wake up without you, without you in my head again. I’m dying, dying to forget about you, that you ever lived.” Been there, experienced that. What’s worse than being so heartbroken over someone that you wish you could just forget them completely? Still clinging to that tiny bit of hope ‘as long as there’s a breath.’
18. “Lalena” by Donovan
There’s so much despair in his voice. It makes the song and breaks me. I’d absolutely name a future daughter Lalena if I didn’t feel like I’d be dooming her to a tragic life.
17. “Mr. Golden Deal” by Tonic
I’ve said for many years that Emerson Hart writes my soul. I don’t know how he does it, but he creeps in there and writes what I can never say or think but feel completely. I’ve always felt like he gets me, probably more than any other artist. This song is for when you feel like someone else has who/what you want or like you are always “holding your tongue when they call another winner” because it’s never you.
16. “Walking By” by Something Corporate
Andrew McMahon is a poet, and there are so many songs that could also be in this spot, but the desperation of this one gets me every time. “And what did I do that you can’t seem to want me? And why do we lie here and whisper goodbyes? Where can I go that your pictures won’t haunt me? What makes it so easy for you to be walking by?” All those questions are so relatable. Kind of like “Dying,” you just want to forget someone and do all you can to avoid them, but you know it’s impossible because you see them everywhere, in everything.
15. “See-Saw” by Youth Group
“Maybe one day she will just say that she’s happy enough…” How sad does someone have to be to just want happy enough? So sad.
14. “She Has No Time” by Keane
“Think about the lonely people and think about the day she found you. Or lie to yourself and see it all dissolve around you.” The falsetto just kills me. This is easily my favourite Keane song, but it’s so sad and beautiful that I can’t cope.
13. “Breathtaking” by Jessica Riddle
This song is so simple with just a piano and vocals, but it’s, well… breathtaking. How many songs are there about someone feeling bad for someone else who lost a loved one?
12.”Come Home” by Elevaters
I have a special history with this song. I first heard it in 2007 when my sister and I met these lovely guys after one of their shows in LA, and they invited us to an intimate jam session a few days later where they played this. It was so raw and real. I remember fighting back the tears as they played it for us because it was so beautiful, and I related to it a bit too much. (Still do.) It’s both sad and encouraging. I never forgot the song or that moment and always wished they’d release it… Flash forward to 2011. They put this up on SoundCloud, and I was ecstatic. It was everything I remembered it to be, and it made me cry all over again. Most of their music is more upbeat, positive, and empowering soul/hip-hop, so this song is a bit unique for them. Though they released a different version with more instruments on their Come Alive album in 2014, I prefer this one because it’s stripped down, just like it was when they played it at that jam session years ago…
11. “Can’t Do This On My Own” by Gangs of Ballet
My friend and I swap (usually sad) music, and he got me into Gangs of Ballet. I will forever blame/thank him for all the tears resulting from this beautiful, heartbreaking song. I love the buildup and the emotion in it. “My love is undivided… My love can’t go to somebody else.”
Check-in: How are we doing, on a scale of 1 to John Cusack In The Rain? Hanging in there?
10. “In The Morning” by Darcie Miner
I promise we’re getting to songs you know, but right now we’re mostly in the Songs You Should Know bit. Remember all those teen artists singing songs about their crushes or whatever? Who didn’t write like that as a teenager? Darcie Miner. I think she was about 14 when she wrote one of my favourite songs ever (“My Angel”), inspired in part by those Philadelphia cream cheese commercials years ago. I’m not sure how old she was when she wrote this one but certainly a teenager. You can tell from her music that she experienced a lot as a child, and thankfully for us, she turned her pain into art. She has many songs that could easily go on this list, but this is one of my favourites.
9. “Every Little Thing” by Dishwalla
It’s truly a shame people don’t know Dishwalla for more than a couple songs from the ’90s. This album is absolutely gorgeous (one of my favourites), and this is one of my all-time favourite songs. It’s simply perfection. It makes me cry because it’s just so emotional, desperate, and obviously incredibly heartbreaking. I always say I’m a sucker for those builds in songs, and that’s true of this one, too. “Will you find out who you are too late to change? I wish I could be every little thing you wanted all the time…” Breaks. My. Heart.
8. “I Can’t Make You Love Me” by Bonnie Raitt
Remember when I said there would be no cliché Adele songs, like “Someone Like You,” on this list? Someone explain to me how that song made the list of 100 saddest songs ever in This Will End In Tears: The Miserablist Guide to Music and this song didn’t. (Then again, “Everybody Hurts” by R.E.M. also made that list, but it’s not actually that sad when you listen to it. Lyrics, people!) But I digress… This song is a classic with so many covers – Bon Iver, George Michael, and Darren Hayes, to name a few favourites – and it is so sad that I actually had it higher up on the list but moved it down to a more appropriate spot because that’s what it deserves.
7. “The Real Thing” by Kenny Loggins
When I listened to my playlist to make this list, this is the one that made me ugly cry the most for many reasons. I don’t think people whose parents are still together or parents who are still together can fully appreciate this song. However, I think divorced parents and children of divorce will absolutely understand its place on this list.
6. “Without Love” by Endochine
I’ve written before about how much I love this whole album that no one else seems to know. Kind of like Gangs of Ballet and Dishwalla, I love the build and the desperation. “I could love you with a broken heart…” So hauntingly beautiful.
5. “Washing of the Water” by Peter Gabriel
Sometimes you can know a song, but it takes the right moment in the right place or time to make you really hear it. That’s how it was with this song. I had it on a playlist for months, but I didn’t really listen closely enough affect me until the moment I needed it. I remember the day it hit me as I was on a bus, and the moment inspired me to buy two journals – a personal one and a music one. I wrote about this song in the music one and wrote about the situation that inspired me in the other one. Within a couple weeks of that moment, possibly even the same day, I decided to make this blog instead. I hate and thank whoever hurt Peter Gabriel enough to make him write this incredibly perfect song. If you listen to it (and I should never have to tell you to listen to a legend like Peter freakin’ Gabriel), I really don’t think I need to explain why it’s on this list and made the title.
4. “Forever and Always” by Parachute
If you read the comments on this video, 99.9% are about how much this song makes them cry – with good reason. It’s a sweet song, but whenever I listen to this album, I always skip it, unless I’m actively trying to make myself cry. It starts with a woman sitting alone, waiting for her partner, who’s late coming home. I won’t spoil it, but you can probably figure it out or just listen to it for yourself and see. Warning: The ending will crush you. I saw Parachute perform this in 2016, and I swear there wasn’t a dry eye in the house.
3. “I’ll Find a Way” by Rachael Yamagata
I mentioned this one in the list of TV scenes that make me cry when it was on Nip/Tuck, and that’s a big part of the reason it makes me cry. I don’t think it’s actually a very straightforward song. I think it’s about that inner turmoil when you want someone but you know you shouldn’t, maybe because you’re with someone else (Reminds me a bit of “Please Help Me, I’m Falling” in that case) or you just know it won’t work but remain conflicted. Either way, I love the lyrics and the way she sings it.
2. “Your Letter” by 112
Aww, he finds a love letter, and all his dreams have come true! How sweet! When the second bridge hits, followed by the one-word change in the chorus… Let’s just say this song has made me cry for nearly 20 years. I don’t imagine it’ll stop anytime soon.
1. “Nearly Morning” by Luke Sital-Singh
If you read the introduction, you knew this was coming, but the song choice itself might be a bit surprising. Considering Luke Sital-Singh’s other work, you may have been expecting something more along the lines of “Benediction,” “Lilywhite,” “Fail For You,” “Killing Me” or any other sad Luke Sital-Singh song. But that’s the thing about this one – it’s not like the others in the kind of sadness it offers. When I was upset about something a few months ago, I listened to Luke, and this was (unexpectedly) the song that made me cry. Kind of like “Everybody Hurts,” this song is like that friend who is there when you’re at your worst, reassuring you that you’re not alone and to hang on because it’s not the end, and tomorrow is a new day. And all of that just makes you cry even more than you already were. There’s a sad hope in it. I think this was actually the song that inspired the Cry Your Eyes Out playlist (though the playlist is named for Luke’s “Nothing Stays The Same”) in a low moment, and it’s the first song on the list. There’s a live version with Gabrielle Aplin that will take your breath away – a common side effect of Luke Sital-Singh’s gorgeous music. I wouldn’t change one millisecond of it because everything about it is just perfect.
Congratulations! You’ve made it to the end! Still holding up okay? Crying? Laughing at me? Just thinking I’m the world’s biggest sap/nutter? Not to worry, I won’t just leave you in a pit of despair forever. These songs are for when you’re going through heartache or just a bad time, but I may eventually share more positive songs that I listen to when I need a little pick-me-up. In the meantime, I’m always looking for some new tearjerkers. What are some songs that make you cry? Share in the comments below.