Songs that make me cry


The other day, I got into a conversation about songs that make people cry. So, I asked my FB peeps what songs made them cry, talked about it with some other people, and came up with my own playlist. On days when you just need a good cry, this should do it.

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The contenders:

1. Simon & Garfunkel, "America (Kathy's Song)"

This song has always really gotten to me. A lot of S&G's songs do, but there is just something in this one that is so bleak.

The line that starts the waterworks: "'Kathy, I'm lost,' I said, though I knew she was sleeping. 'I'm empty and aching and I don't know why.'"

2. Warren Zevon, "Keep Me In Your Heart."

I think this one gets me because I connect it to the saddest part of Joan of Arcadia. I had heard it before then, but it wasn't something that had stuck in my mind.

The line that starts the waterworks: "These wheels keep turnin', but they're runnin' out of steam. Keep me in your heart for awhile."

3. Stephen Trask, "The Origin of Love" (from Hedwig & the Angry Inch)

I cried the first time I heard this, and if I pay attention when it's on, I'll cry every time. It's just such a sad, beautiful story.

The line that starts the waterworks: "And the storm clouds gathered above, into great balls of fire." If that doesn't do it? "The last time I saw you, we were just split in two. You was lookin' at me, I was lookin' at you. You had a way so familiar, I could not recognize, cuz you had blood in your face. I had blood in my eyes."

4. Counting Crows, "Anna Begins"

This one is, I'm sure, partially nostalgia. This is a big high school album for me, and though none of the actual events that took place make me feel sad anymore, the feeling is still there.

The line that starts the waterworks: "She can't stop shaking, and I can't stop touching her. And this time, when the kindness falls like rain, it washes her away. And Anna begins to change her mind."

5. Kris Kristofferson, "Casey's Last Ride"

There are a ton of Kristofferson songs I could have added to this list--the man is a tearjerker--but this one is so haunting. And the line that makes me cry is seriously like turning on a faucet.

The line that starts the waterworks: "Oh,' she said, 'I suppose you seldom think about me.' 'Now,' she said, 'now that you've a family of your own.' 'Still,' she said, 'it's so blessed good to feel your body.' 'Lord,' she said,' Casey it's a shame to be alone.'"

6. Johnny Cash, "Hurt"

This one is a no-brainer. And if you think it won't make you cry, watch the video. I can't even think about it...

The line that starts the waterworks: "What have I become, my sweetest friend? Everyone I know goes away in the end."

7. Sarah McLaughlin, "Full of Grace"

Sarah McLaughlin is another one who has lots of tearjerkers. This one is the most poignant to me, though, for TV reasons. Every time I hear it, I see Buffy pulling away on the bus during the last episode of Season 2. So heartbreaking.

The line that starts the waterworks: "I know I could love you much better than this. Full of grace. It's better this way." or "I'm pulled down by the undertow. Never thought I could feel so low. Oh, darkness, I feel like letting go."

8. The Pogues, "And the Band Played Waltzing Mathilda"

Too cliched? Too bad.

Where I start crying: "And the band played 'Waltzing Mathilda," as we stopped to bury our slain. We buried ours, and the Turks buried theirs, and then we started all over again."

9. Israel Kamakawiwo'ole, "Somewhere Over the Rainbow"

The original of this song never did anything for me, but this version slays me. I heard a special on NPR once about the sad and beautiful life of Israel Kamakawiwo'ole, and I've gotten misty eyed every time I've heard it since then.

Where it gets me: When he breaks into the "What a Wonderful World" part.

10. Jim Croce, "Time in a Bottle"

Another gimme. This one was meant to make people cry, I think. And the older I get, the sadder it gets.

The crying part: The chorus. "There never seems to be enough time to do things you want to do once you find them. I've looked around enough to know that you're the one I want to go through time with."

11. Tim McGraw, "Angry All the Time"

I'm not a Tim McGraw fan or anything, but this song breaks my heart. So much bitterness and wasted time. Gah. It kills me.

The line where I start crying: "Our boys are strong, the spitting image of you when you were young. I hope someday they can see past what you have become. I remember every time I said I'd never leave. But what I can't live with is memories of the way you used to be."

12. Stevie Nicks, "Landslide"

Another fairly classic choice. Stevie Nicks' voice is spooky anyway, and this song is just so desperate and hopeful.

The sprinkler starts at: "But time makes you bolder. Children get older. I'm getting older, too."

13. Pearl Jam, "Black"

Another piece of nostalgia, but seriously, listen to the words! It's so painful.

The part that makes me cry the fastest: "And all I taught her was everything."

14. Jeff Buckley, "Hallelujah"

I've mentioned here before that this is my favorite song. This is not my favorite version, but it's the most tear-jerking version. The words are heartbreaking in that special, Cohen way, and it also makes me remember that sad sad sad episode of The West Wing.

Saddest part: "I've seen your flag on the marble arch, and love is not a victory march. It's a cold and it's a broken hallelujah."

15. Michelle Branch, "Goodbye to You"

This one is all about Buffy. At the end of "Tabula Rosa," when Tara moves out and Giles leaves. You just know it's only the beginning of shit going really really bad.

The crying part: "And it hurts to want everything and nothing at the same time. I want what's yours and I want what's mine. I want you, but I'm not giving in this time."

16. Brad Paisley & Allison Krauss, "Whiskey Lullaby"

I have no personal associations with this song, I just find it exceptionally sad. There's something particularly poignant about people drinking themselves to death. Such a slow, humiliating suicide.

The tears start at: "Life is short, but this time it was bigger. Than the strength he had to get up off his knees."

17. Eric Clapton "Tears in Heaven"

Confession: I went through a phase where I was obsessed with the film "Rush." Since then, this incredibly typical song has torn me up.

The part that kills: "I'll find my way, through night and day. Cuz I know I just can't stay here in heaven."

18. Bonnie Raitt, "I Can't Make You Love Me"

Yet another one with TV ties, but these ones are really vague. I believe I heard this song the first time on General Hospital. I have no idea what the context was, but I remember being just so broken up about the hopelessness and the way the singer is conceding to defeat. So sad.

The lyric that gets to me the most: The part where her voice gets softer and she says "and you don't."

19. Portishead, "Roads"

Some of the songs on the list are high school, this one is immediately post-college. God, it makes a lump rise in my throat just to think about that time.

The faucet starts at: "Ooh, can't anybody see? We've got a war to fight. Never find our way. Regardless of what they say. How can it feel...this wrong?" (And yes, that is the very first line.)

20. Hollies, "He Aint' Heavy, He's My Brother"

I have no context for this song. I don't remember when I first heard it. But the lyrics just blow me away. It's so simple, and so moving.

I cry when: they sing the chorus.

21. George Jones, "He Stopped Lovin' Her Today"

Country music is all about the sad song, but it doesn't come a whole lot sadder than this one. I actually get misty when I heard "It's Been a Good Year for the Roses," too, but I didn't want to feature George Jones on the list twice.

The line that gets to me: "I went to see him just today, but I didn't see no tears. All dressed up to go away. First time I'd seen him smile in years," and then it goes into the first chorus.

22. The Sundays, "Wild Horses"

Yet ANOTHER Buffy song! This one's from the Prom episode, which was the first time Buffy had me in tears (though certainly not the last). I am such a sucker.

The lyric that gets me started: "Faith has been broken. Tears must be cried.Let's do some living after we die."

23. Jim McCann, "From Clare to Here"

I don't think there is any version of this song that won't make me cry if I am already feeling homesick. It's my ultimate homesickness song.

Line that gets to me the most: The chorus. "It's a long long way. It gets further by the day. It's a long way from Clare to here."

24. John Prine, "Sam Stone"

A song about an addicted vet? How's that gonna not make you well up?

The waterworks start with: The first "there's a hole in Daddy's arm where the money goes. Jesus Christ died for nothin, I suppose."

25. Willie Nelson, "He Was a Friend of Mine"

I put the Cat Power version on this list, since I couldn't access Willie's, but it's really the one Willie does, featured in Brokeback Mountain, that gets me. It's just so freaking...sad.

I start crying: at the very beginning and then the whole way through.


The Zevon song is even sadder thinking that he was dying when he wrote it. "I'm tied to you like the buttons on your blouse, keep me in your heart for awhile."

Another one that gets me is Joni Mitchell's Circle Game, but that's mostly because my daughter is getting married in the fall.

I'm working my way through some of this list- some are already favorites of mine like "Waltzing Mathilda" by the Pogues, and "From Clare to Here" (Nancy Griffith's version), and I have no idea where I heard this version of "Somewhere Over the Rainbow" but it's really sweet and what a wonderful voice! I'm so happy to know who sang this version, wish I could remember where I heard it though.

I LOVE "Full of Grace" which I also first heard on that episode of Buffy. I played that scene over and over until I got myself a copy of the song so I could play it without the video.

Really great list.

Yes, really great list and couldn't agree more about the need to cry now and again. I love so many songs you have here already (and they make me cry too). I also love the new ones you've exposed me too.
On my own list I would add two that come to mind right away. I have my own personal stories and waterworks reactions behind these two sad songs: Decemberists "The Engine Driver" (particularly the chorus "And if you don't love me let me go" and Dead Can Dance "The Ubiquitous Mr Lovegrove" (Never let it be said I was untrue; I never found a home inside of you; never let it be said I was untrue; I gave you all my time)...

Maybe this is because I'm a musician, but my cry list is completely unlike this one.

I'm hardly ever moved to tears by the recording of a slow-dance or ballad - songs with samey dynamics do not tend jerk tears from my eyes. I get more choked up by big crescendos or really fierce vocal performances. For example, "Landslide" doesn't really get me, but "Go Your Own Way" sometimes does.

That said, a ballad that also has one of those big dynamic moments will definitely crush me - the last verse of Tori Amos's "Playboy Mommy" comes to mind, as does Carole King's version of the poem "Pierre."

Prince does an awesome version of "I Can't Make You Love Me."

The story behind "Tears in Heaven" gets me every time -- Clapton wrote it for his 4 year old son who died in a tragic accident.

Billy Idol "Eyes Without A Face" gets me water-eyed almost every time. You can add that one to the list.

Ol Shep by Elvis, Three Wooden Crosses Randy Travis, Conway Twitty Who did they think he was, Would you Crucify him by John Michael Talbot, Here I am lord, John MIchael Talbot, Wisteria RIchard SHindell, Cold Missouri Waters, Richard shindell, That's my job, Conway Twitty, The only Way Mark Erelli, Speaking with an Angel, Lucy Kaplansky, Family Dar Williams, Puff the Magic Dragon Peter Paul and Mary. Just the Hem of his Garment Sam Cooke, A change gonna Come Same Cooke, Father and Son Cat Stevens.
Thought I'd see a few of mine own here, didn't so i added them.

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