country music The Saddest Country Songs  

Ranker Music
9.5k votes 1.2k voters 52.2k views 100 items

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
332 76
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He Stopped Loving Her Today A song about a mans undying love for a woman

2
341 88
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Whiskey Lullaby Brad Paisley, Alison Krauss - A sad song about alcholosim and death.

3
159 31
Remember When by Alan Jackson is listed (or ranked) 3 on the list The Saddest Country Songs

4
222 65
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If You're Reading This Based on a letter s fallen soldier writes home to his family.

5
183 61
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Go Rest High On That Mountain A song about the passing of a loved one

6
157 49
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I’m Already There A song about a lost loved one who is already in heaven.

7
205 75
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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'

8
155 51
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If Heaven Wasn’t So Far Away A song about missing a grandfather who has passed away.

9
156 56
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Alyssa Lies A sad song about a little girl who is a victim of abuse.

10
168 67
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I Drive Your Truck A song about a man who misses his buddy who has passed away.

11
94 24
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RodPatrick added Hurt Johnny Cash

12
176 75
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What Hurts the Most A song about wondering what could have been

13
145 58
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Concrete Angel A song about a forgotten little girl who has to take care of herself.

14
114 42
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Always on My Mind Willie Nelson - A song about regrets and unforgettable love.

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15
117 45
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I'm So Lonesome I Could Cry Johnny Cash - The title says it all

16
120 48
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Holes in the Floor of Heaven Another sad song about loss, love and life

17
120 51
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American Soldier Toby Keith - A song about soldiers who must go off to fight.

18
122 54
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Travelin' Soldier Dixie Chicks - A song about a soldier who doesn't come home

19
107 44
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Just a Dream A song about a young couple marrying before the man goes off to war

20
89 32
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jeremy-fisher added Don't Laugh at Me Mark Wills

21
113 51
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Paint Me a Birmingham A song about lost love and plans of a life that never came

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22
96 42
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How Can I Help You Say Goodbye Patty Loveless - A song about life's many sad occassions

23
94 44
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Coat of Many Colors Dolly Parton - A song about bullying and unkind children

24
61 21
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RodPatrick added The House That Built Me Miranda Lambert

25
58 19
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RodPatrick added Blue Eyes Crying in the Rain Willie Nelson

26
94 46
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When I Call Your Name Vince Gill - A sad song about a man finding his wife has left him.

27
120 67
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Jolene A song about a woman pleading to beuatiful Jolene not to steal her man.

28
76 36
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Wish You Were Here A song about a lover lost in a plane crash

The Best Country Songs About Work

29
80 40
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Your Cheatin' Heart Patsy Cline - A song about a cheating lover

30
76 37
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Help Me Make It Through the Night A sad song about a night of love that shouldn't have been

31
49 17
Please Remember Me by Tim Mcgr... is listed (or ranked) 31 on the list The Saddest Country Songs

32
74 37
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I’m No Stranger to the Rain The rain, that perfect and constant euphamism for sadness and lonliness.

33
58 26
You Should Be Here is listed (or ranked) 33 on the list The Saddest Country Songs
AidanBitterman added You Should Be Here

34
78 43
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The Best I Ever Had A song about remembering a lost love.

35
63 32
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erika-steen added The Little Girl John Michael Montgomery

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36
72 41
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The Baby A song about a son and his dying mother.

37
71 42
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God's Will A song about a terminally sick child

38
52 26
Drink a Beer is listed (or ranked) 38 on the list The Saddest Country Songs
AidanBitterman added Drink a Beer

39
48 24
Colder Weather is listed (or ranked) 39 on the list The Saddest Country Songs
FireFront55 added Colder Weather

40
35 14
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DebbyHood added Don't Close Your Eyes Keith Whitley

41
28 8
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DebbyHood added Anymore Travis Tritt - "my heart can't take the beating, Not having you to hold, A small voice keeps repeating, Deep inside my soul. it says I can't keep pretending, I don't love you anymore."

42
40 19
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RodPatrick added I Told You So Randy Travis

The Best Country Songs About Food

43
66 43
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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.

44
59 37
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I’m Gonna Love You Through It A song about loving and caring for someone through their battle with cancer.

45
67 49
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Highway 20 Ride Zac Brown Band - A song about a man who must be away from his family.

46
58 42
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A Picture of Me (Without You) A devasted lover sings about life without his love.

47
30 15
For the Good Times Ray Price is listed (or ranked) 47 on the list The Saddest Country Songs
DebbyHood added For the Good Times Ray Price "Don't look So Sad, I know it's over. But Life goes on,and this old world will keep on turning. just be glad we had this time to spend together. theres' no need to watch the bridges that we're burning"  

48
58 44
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Today I Started Loving You Again A song about realizing love too late.

49
55 42
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Love,Me A song about lover's trying to be together whatever the consewuences.

50
24 12
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