music The Saddest Country Songs  

4.8k votes 592 voters 32.7k views 85 items 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
183 39
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Whiskey Lullaby Brad Paisley, Alison Krauss - A sad song about alcholosim and death.

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2
172 36
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He Stopped Loving Her Today A song about a mans undying love for a woman

3
99 30
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If You're Reading This Based on a letter s fallen soldier writes home to his family.

4
88 33
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Go Rest High On That Mountain A song about the passing of a loved one

5
99 42
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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
83 33
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I Drive Your Truck A song about a man who misses his buddy who has passed away.

7
81 33
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Alyssa Lies A sad song about a little girl who is a victim of abuse.

8
96 45
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What Hurts the Most A song about wondering what could have been

9
79 33
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Concrete Angel A song about a forgotten little girl who has to take care of herself.

10
72 28
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Holes in the Floor of Heaven Another sad song about loss, love and life

11
69 26
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American Soldier Toby Keith - A song about soldiers who must go off to fight.

12
71 28
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I’m Already There A song about a lost loved one who is already in heaven.

13
63 23
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If Heaven Wasn’t So Far Away A song about missing a grandfather who has passed away.

14
77 36
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Jolene A song about a woman pleading to beuatiful Jolene not to steal her man.

15
63 26
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I'm So Lonesome I Could Cry Johnny Cash - The title says it all

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16
65 29
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Paint Me a Birmingham A song about lost love and plans of a life that never came

17
62 30
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When I Call Your Name Vince Gill - A sad song about a man finding his wife has left him.

18
44 16
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jeremy-fisher added Don't Laugh at Me Mark Wills

19
63 32
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Just a Dream A song about a young couple marrying before the man goes off to war

20
47 19
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Wish You Were Here A song about a lover lost in a plane crash

21
61 31
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Always on My Mind Willie Nelson - A song about regrets and unforgettable love.

22
49 23
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How Can I Help You Say Goodbye Patty Loveless - A song about life's many sad occassions

23
62 34
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Travelin' Soldier Dixie Chicks - A song about a soldier who doesn't come home

24
54 29
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Coat of Many Colors Dolly Parton - A song about bullying and unkind children

25
46 25
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Your Cheatin' Heart Patsy Cline - A song about a cheating lover

26
47 27
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The Best I Ever Had A song about remembering a lost love.

27
44 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

28
45 27
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The Baby A song about a son and his dying mother.

29
39 24
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I’m No Stranger to the Rain The rain, that perfect and constant euphamism for sadness and lonliness.

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30
40 26
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God's Will A song about a terminally sick child

31
42 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.

32
16 3
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RodPatrick added Hurt Johnny Cash

33
32 19
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erika-steen added The Little Girl John Michael Montgomery

34
15 3
Remember When by Alan Jackson is listed (or ranked) 34 on the list The Saddest Country Songs

35
13 2
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RodPatrick added Blue Eyes Crying in the Rain Willie Nelson

36
35 24
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Love,Me A song about lover's trying to be together whatever the consewuences.

37
40 29
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Highway 20 Ride Zac Brown Band - A song about a man who must be away from his family.

38
14 6
You Should Be Here is listed (or ranked) 38 on the list The Saddest Country Songs
AidanBitterman added You Should Be Here

39
33 26
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Today I Started Loving You Again A song about realizing love too late.

40
32 25
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I’m Gonna Love You Through It A song about loving and caring for someone through their battle with cancer.

41
34 28
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Somewhere in My Broken Heart Billy Dean - A sad song about heartache

42
14 7
Drink a Beer is listed (or ranked) 42 on the list The Saddest Country Songs
AidanBitterman added Drink a Beer

43
11 4
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RodPatrick added I Told You So Randy Travis

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44
32 29
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A Picture of Me (Without You) A devasted lover sings about life without his love.

45
12 7
Love Triangle is listed (or ranked) 45 on the list The Saddest Country Songs
FireFront55 added Love Triangle

46
11 6
Colder Weather is listed (or ranked) 46 on the list The Saddest Country Songs
FireFront55 added Colder Weather

47
9 4
Please Remember Me by Tim Mcgr... is listed (or ranked) 47 on the list The Saddest Country Songs

48
10 6
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RodPatrick added The House That Built Me Miranda Lambert

49
28 28
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Believe A song about losing an old friend

50
21 20
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Craig Brewster added Chiseled in Stone Vern Gosdin