So, I love well-written sad songs, especially ones about love. I loved them when I was an overemotional teenager and I love them now as a stable and happy young adult. So here are my top ten sad songs about love.
My Top 10 Favorite Sad Songs About Love
10. I Know It’s Over by The Smiths
The Smiths are one of those bands that you just don’t like as much when you’re happy. This is still a good one though, classically and comically morose the way a Morrissey song should be.
Heartwrenchingest line: “And as I climb into an empty bed…oh well, enough said. I know it’s over, but still I cling. I don’t know where else I can go. Over, over, over, over, over…”
9. Landslide by Fleetwood Mac/The Dixie Chicks
My god. I submit that one cannot listen to this song two times in a row with dissolving into either tears or giggles. Listening to this song is like having an emotional brick getting thrown at your head.
Heartwrenchingest line: “Oh, I’ve been afraid of changing ‘cause I’ve built my life around you. But time’s getting colder, children get older and I’m getting older too.”
8. Someone Great by LCD Soundsystem
It took me a very long time to warm to LCD Soundsystem, but at some point I’d been to enough hipster parties where the only music welcome is MIA or LCD Soundsystem that I kind of warmed to them. And this is a really striking song, admittedly, with its robotic quality and lyrics that are at once deadpan and very sad. It’s about a break-up or a death or both – I’m not really sure.
Heartwrenchingest lines: “I wish that we could talk about it…but then, that’s the problem.” “The worst is all the lovely weather. I'm sad it's not raining. The coffee isn't even bitter. Because what's the difference?”
7. I Felt Your Shape by The Microphones
Yeah, it’s another really good and really sad song.
Heartwrenchingest line: “But I don’t know, the nights are cold, and I remember warmth. I could’ve sworn I wasn’t alone.”
6. Night Windows by The Weakerthans
The Weakerthans are a not-so –great little band that I have nevertheless loved very dearly since early high school. They basically made the same album three times in a row, and this is a gem from a recent one.
Heartwrenchingest line: “But you're not coming home again, and I won't ever get to say:
Remember how I'm sorry that I miss the way it could be.”
5. Overs by Simon and Garfunkel
There might not have been anything revolutionary about this song, but it’s so well written and the timing within it is incredible. The song itself sounds like it might shatter along with the rattling teacups.
Heart-wrenchingest line: “We might as well be apart. It hardly matters, we sleep separately, and drop a smile passing in the hall. But there’s no laughs left, ‘cause we laughed them all. And we laughed them all in a very short time.”
4. Galveston by Glen Campbell
The writer of this song claimed it was about the Spanish-American War, not Vietnam. Strange.
Heartwrenchingest line: “Galveston, oh Galveston. I am so afraid of dying before I’ve dried the tears she’s crying.”
3. Desperado by Linda Ronstadt
I know The Eagles did the famous version of this song, but The Eagles can suck it, because that’s a travesty of justice. Linda Ronstadt has pipes and her version should be the canonical one.
Heartwrenchingest line: “And freedom, oh freedom, well that’s just some people talkin’. Your prison is walking through this world all alone.”
2. I’m going to cheat here and do six-for-one. There are six, great, sad Magnetic Fields songs here, as I didn’t want to waste six spots on them but couldn’t bear to drop any of these. Stephen Merritt is just a downright gloomy person, but it works out well for his songwriting.
Deep Sea Diving Suit (apparently it's not available on youtube)
Heartwrenchingest line: “I never thought you’d turn on me ‘cause you’re my best friend. You say I never offered you a thing in the end. And now you wouldn’t trust me with a grain of sand. And I’m sorry, but how can I get to you, stuck in my 50-pound lead boots, stuck in my deep sea diving suit?”
When You're Old and Lonely Heartwrenchingest line: “When you’re old and lonely you will wish you’d married me. I could build a fire for you and bring you cakes and tea. When you’re cold and lonely I’ll be waiting by the phone. You can call me up and tell me how you’re all alone, all alone.”
Grand Canyon Heartwrenchingest line: “If I was the Grand Canyon, I’d echo everything you say. But I’m just me, I’m only me, and you used to love me that way, so you know how to love me that way.”
No One Will Ever Love You Heartwrenchingest line: “If you don’t mind, why don’t you mind? Where is your sense of indignation? You are too kind – much too kind. Where is the madness that you promised me?”
The Saddest Story Ever Told Heartwrenchingest line: “We used to go out on the summer nights and dance in the neon rain. We used to hold hands at the movie show but we’ll never hold hands again. Those days are gone, you and I were young those summer nights. You’ll see the world, dying for a girl you’ll never find. And then we’ll quietly grow old, the saddest story ever told.”
I Don’t Really Love You Anymore Heartwrenchingest line: “I don’t have to love you now if I don’t wish to. I won’t see you anyhow if that’s an issue. Because I am a gentleman – think of me of just your fan, who remembers every dress you ever wore. Just a bad comedian your new boyfriend’s better than, ‘cause I don’t really love you anymore.”
1. Good Year For the Roses by Elvis Costello/George Jones
Once a month or so for several years now, this song will pop into my mind (or sometimes Ruth’s mind) and we’ll sing it and then discuss its greatness for the next ten minutes or so, and then we'll tell someone else about its greatness. I love this song. I sing it in the shower. I sing it when I’m feeling bored or thoughtful. It just hits me right in the heart in the best way possible, and it never gets old to me.
Heartwrenchingest line: “I can hardly bear the sight of lipstick on the cigarettes there in the ash, tray, lying cold the way you left them, but at least your lips caressed them while you packed. Or the lip ring on the half-filled cup of coffee that you bought and didn’t drink. But at least you thought you wanted it – that’s so much more than I can say for me.”
Honorable mention: Superstar by The Carpenters.
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