The 30 Day Song Challenge: Day 4

Today’s category is…

A Song That Makes You Sad.

Here are the staff picks:

Kevin Coyne: “No Time to Cry” – Iris Dement

Most songs that I find sad don’t have a lingering impact after the last note fades.  “No Time to Cry” cuts so close to the bone that it brings on waves of melancholy. It captures my reality closer than any other song. It’s ironic that a song that talks about suppressing grief so it doesn’t surface is the one that makes the suppressed grief surface.

Leeann Ward: “Goodbye” – Patty Griffin

Suddenly losing my mother-in-law less than a month ago makes this song cut close to the bone right now. I suspect it will for a long time.

Tara Seetharam: “We Belong Together” – Gavin DeGraw

Something about the combination of melody, urgency and DeGraw’s nuanced delivery hits my gut every time I hear this song.


  1. I’ll say “Whiskey Lullaby” by Brad and Alison. It’s a beautiful song, but it is really sad. I think that if anyone other than Alison had been the duet partner, the song wouldn’t have been as effective. Her soft tone brings the sadness out. Brad’s voice is as good as its ever been, bringing the pain out of the lyrics.

    For some non-country, I’ll say “My Immortal” by Evanescence. Amy Lee has a great voice, especially on a piano ballad like this one. Her song of realizing that her almost lover has left her hits me like a ton of bricks. For most of the song, Amy’s voice and a piano is just about all there is to hear. That’s all she really needed anyway.

  2. On the country side, I have to agree with “Whiskey Lullaby”. On the pop side, “Desperate” by David Archuleta.

  3. Oh lord, there are so many but “I Miss You A Little” by John Michael Montgomery and “She’s Gonna Fly” Collin Raye are pretty tear-invoking but “How Can I Help You Say Goodbye” is hands-down the one that brings me a tear every time.

  4. Wow…I kind of expected to see the Queen of Heartbreak (aka Reba) on here somewhere. For My Broken Heart, If I Had Only Known, or She Thinks His Name Was John both came to mind right away.

  5. Faith Hill – Wild Frontier
    Shania Twain- Home ain’t where his heart is
    Steve Azar- Waiting on Joe
    Lee Ann Womack- Last Call
    Roger Miller- You don’t want my love
    Bonnie Riatt- I can’t make you love me
    Lori McKenna- Your next lover
    Missy Higgins- Where I stood
    Commodores – Still
    Don Mclean- Vincent
    Fischer Z- So long
    Gilbert o’Sullivan – Nothing Rhymed
    Eric Carmen- Boats against the current
    Neil Diamond- Solitary man
    Michael McDonald – I can let go
    Sam Cooke- A change is gonna come
    Doug Ashdown – Winter in America
    And many more

  6. Brad Paisley’s “Whiskey Lullaby”, Alan Jackson’s “Monday Morning Church and “Here in the Real World”, and Troy Cassar-Daley’s “River Boy”.

  7. Top two at the moment:
    Bury Me Far (From My Uniform), by Joe Pug

    You’ll Never Leave Harlan Alive, the Patty Loveless version

  8. Tammy Cochran’s song about her brothers, “Angels in Waiting”, always gets me, especially the first line of the 3rd verse: “They always knew they’d never grow old”.

  9. I think the saddest song I’ve ever heard is “God Bless the Child” by Shania twain. Esp the part about “when a child spirit’s Broken, he feels all hope is gone…”

  10. This is very hard, since there are so many that do it, but here are ten of them:

    I WILL ALWAYS LOVE YOU–Linda Ronstadt
    ALL I KNOW–Art Garfunkel
    DO YOU KNOW WHO I AM?–Elvis Presley
    WASTED TIME–The Eagles
    LONG LONG TIME–Linda Ronstadt
    ONCE UPON A TIME IN THE WEST–Ennio Morricone
    COLORADO–Linda Ronstadt
    IT’S MIDNIGHT–Elvis Presley

  11. @Greg,

    I almost put “For My Broken Heart” by McEntire but the hopefulness at the end of the song makes it a kind of song that gives me hope, but here are some McEntire songs that make me sad:

    “Somebody Should Leave”
    “All Dressed Up”
    “The Greatest Man I Never Knew”
    “If I Had Only Known”
    “She Thinks His Name Was John”
    “He Gets That From Me”
    “She Can’t Save Him” (with Trisha Yearwood)

  12. Reba’s “The Greatest Man I Never Knew” is definitely on top and also her “She Thinks His Name Was John”

  13. George Jones, “A Good Year For the Roses.”

    And I second Alan Jackson’s “Monday Morning Church.” That song just gets me…and the video takes it to another level, too.

  14. Dierks Bentley:”Down in the Mine”
    Kathy Matea: “Where’ve You Been”
    can’t decide which one makes me cry first, but I always cry hearing either of these

  15. The Dixie Chicks “Home” and “Top of the World” are probably one of the most depressing songs I have heard.

    And I know it’s not Reba’s song but I remember she sang a song with the lyrics “so far away doesn’t anyone stay in one place anymore” on her sitcom honoring a friend that had past.

    On the rock side probably “Wish You Were Here” by Pink Floyd.

  16. While Gary Allan’s Tough All Over seems the obvious choice for the most sad songs given it was recorded after his wife committed suicide, I find two other classics of his from the Smoke Rings in the Dark album to be the quintessential sad songs– the title track and “Don’t Tell Momma I Was Drinking.”

    On the pop side, I found the 1996 George Michael cover of Bonnie Ryatt’s “I Can’t Make You Love Me” even more beautifully aching than her original, and her version was entry sad as it was.

  17. “Wind beneath my wings” Bette Midler — sung by my Aunt at my other Aunt’s funeral.

    “Imagine” by John Lennon — played at my father’s funeral.

    “One Sweet Day” by Mariah/Boys II Men — reminds me that one day I’ll be with them.

    Can’t listen to any of these songs without crying…

  18. Patty Loveless’ plaintive East Kentucky twang is the best musical device to make me feel the sadness in a song, as she does so well with songs like “How Can I Help You To Say Goodbye”, “You Don’t Even Know Who I Am”, and my personal favorites “Here I Am” and “To Have You Back Again”.

    Also, great as she is, Reba cannot be the “heartbreak queen” as long as there’s a Tammy Wynette album somewhere. IMHO.

  19. “Ships of Heaven” by Blackhawk. Made me feel mildly sad the first time I listened to it, and then I made the mistake of listening to it a couple days after my grandmother died and I can’t bring myself to listen to it again. I also cannot bear to hear Patty Loveless’ “How Can I Help You To Say Goodbye.”

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