music The Saddest Country Songs  

4.4k votes 560 voters 31k views 84 items Follow Embed

List Rules Vote up the saddest country songs.

Few things are as difficult as missing someone you love, heartache, or death. Whether they have passed away, have moved on, or are just not near you, these can be difficult things to deal with. Often these are topics that the saddest of country songs deal with. The best of these songs on this list are the best.
 

These saddest country songs provide kind of emotional connection that musicians hope people discover in their music. They are heartbreaking and often make us cry. They provide the type of emotion that gives us solace.
 

Vote up the greatest country songs about feeling sad below, or add a song makes you sad and want to cry whenever you hear it, if it isn't already on the list.
list ordered by

1
+ - 163 34
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He Stopped Loving Her Today A song about a mans undying love for a woman

The Best Country Songs for Weddings The Best Rock Vocalists

2
+ - 171 38
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Whiskey Lullaby Brad Paisley, Alison Krauss - A sad song about alcholosim and death.

3
+ - 88 29
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If You're Reading This Based on a letter s fallen soldier writes home to his family.

4
+ - 84 32
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Go Rest High On That Mountain A song about the passing of a loved one

5
+ - 93 40
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Don't Take the Girl Tim McGraw - A tale of a young man's life and his sad pleas not to 'take the girl'

6
+ - 79 32
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I Drive Your Truck A song about a man who misses his buddy who has passed away.

7
+ - 77 31
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Alyssa Lies A sad song about a little girl who is a victim of abuse.

8
+ - 91 42
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What Hurts the Most A song about wondering what could have been

9
+ - 76 32
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Concrete Angel A song about a forgotten little girl who has to take care of herself.

10
+ - 62 22
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If Heaven Wasn’t So Far Away A song about missing a grandfather who has passed away.

11
+ - 67 27
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I’m Already There A song about a lost loved one who is already in heaven.

12
+ - 65 26
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American Soldier Toby Keith - A song about soldiers who must go off to fight.

13
+ - 66 27
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Holes in the Floor of Heaven Another sad song about loss, love and life

14
+ - 72 35
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Jolene A song about a woman pleading to beuatiful Jolene not to steal her man.

15
+ - 60 26
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I'm So Lonesome I Could Cry Johnny Cash - The title says it all

The Best Fast Country Songs 16 Songs That Don't Mean What You Think They Do

16
+ - 61 28
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Paint Me a Birmingham A song about lost love and plans of a life that never came

17
+ - 62 31
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Just a Dream A song about a young couple marrying before the man goes off to war

18
+ - 41 15
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Don't Laugh at Me Mark Wills

19
+ - 48 21
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How Can I Help You Say Goodbye Patty Loveless - A song about life's many sad occassions

20
+ - 44 18
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Wish You Were Here A song about a lover lost in a plane crash

21
+ - 58 30
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When I Call Your Name Vince Gill - A sad song about a man finding his wife has left him.

22
+ - 58 30
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Always on My Mind Willie Nelson - A song about regrets and unforgettable love.

23
+ - 57 34
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Travelin' Soldier Dixie Chicks - A song about a soldier who doesn't come home

24
+ - 50 28
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Coat of Many Colors Dolly Parton - A song about bullying and unkind children

25
+ - 43 24
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Your Cheatin' Heart Patsy Cline - A song about a cheating lover

26
+ - 44 26
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The Best I Ever Had A song about remembering a lost love.

27
+ - 43 26
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The Baby A song about a son and his dying mother.

28
+ - 36 22
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I’m No Stranger to the Rain The rain, that perfect and constant euphamism for sadness and lonliness.

29
+ - 40 26
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Help Me Make It Through the Night A sad song about a night of love that shouldn't have been

The Best Country Songs About Memories Things You Always Forget

30
+ - 31 18
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The Little Girl John Michael Montgomery

31
+ - 38 25
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God's Will A song about a terminally sick child

32
+ - 39 27
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Highway 20 Ride Zac Brown Band - A song about a man who must be away from his family.

33
+ - 13 2
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Hurt Johnny Cash

34
+ - 37 28
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Don’t It Make My Brown Eyes Blue It's right there in the title, this is a song for crying.

35
+ - 33 24
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Love,Me A song about lover's trying to be together whatever the consewuences.

36
+ - 10 2
Remember When by Alan Jackson is listed (or ranked) 36 on the list The Saddest Country Songs

37
+ - 9 1
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38
+ - 31 24
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I’m Gonna Love You Through It A song about loving and caring for someone through their battle with cancer.

39
+ - 30 25
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Today I Started Loving You Again A song about realizing love too late.

40
+ - 31 27
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Somewhere in My Broken Heart Billy Dean - A sad song about heartache

41
+ - 10 5
You Should Be Here is listed (or ranked) 41 on the list The Saddest Country Songs

42
+ - 10 6
Drink a Beer is listed (or ranked) 42 on the list The Saddest Country Songs

43
+ - 10 6
Love Triangle is listed (or ranked) 43 on the list The Saddest Country Songs

The Best Country Songs About Sports The Best Netflix Original Comedy Movies

44
+ - 20 18
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Chiseled in Stone Vern Gosdin

45
+ - 9 6
Colder Weather is listed (or ranked) 45 on the list The Saddest Country Songs

46
+ - 6 3
Please Remember Me by Tim Mcgr... is listed (or ranked) 46 on the list The Saddest Country Songs

47
+ - 28 29
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A Picture of Me (Without You) A devasted lover sings about life without his love.

48
+ - 26 27
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Believe A song about losing an old friend

49
+ - 6 4
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I Told You So Randy Travis

50
+ - 25 27
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I'll Wait for You A song about a husband who is never home and his ill wife.