Country Music The Saddest Country Songs  

Ranker Music
9.7k votes 1.3k voters 54.7k 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.

1
345 82
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He Stopped Loving Her Today A song about a mans undying love for a woman

2
355 92
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Whiskey Lullaby Brad Paisley, Alison Krauss - A sad song about alcholosim and death.

3
168 36
Remember When by Alan Jackson is listed (or ranked) 3 on the list The Saddest Country Songs

4
231 67
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If You're Reading This Based on a letter s fallen soldier writes home to his family.

5
189 63
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Go Rest High On That Mountain A song about the passing of a loved one

6
166 53
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I’m Already There A song about a lost loved one who is already in heaven.

7
212 78
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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
162 53
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If Heaven Wasn’t So Far Away A song about missing a grandfather who has passed away.

9
160 57
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Alyssa Lies A sad song about a little girl who is a victim of abuse.

10
176 68
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I Drive Your Truck A song about a man who misses his buddy who has passed away.

11
100 26
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RodPatrick added Hurt Johnny Cash

12
180 76
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What Hurts the Most A song about wondering what could have been

13
151 60
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Concrete Angel A song about a forgotten little girl who has to take care of herself.

14
126 48
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Holes in the Floor of Heaven Another sad song about loss, love and life

Famous Actors Who Were Almost James Bond

15
120 45
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I'm So Lonesome I Could Cry Johnny Cash - The title says it all

16
114 43
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Always on My Mind Willie Nelson - A song about regrets and unforgettable love.

17
124 52
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American Soldier Toby Keith - A song about soldiers who must go off to fight.

18
127 55
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Travelin' Soldier Dixie Chicks - A song about a soldier who doesn't come home

19
92 32
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jeremy-fisher added Don't Laugh at Me Mark Wills

20
110 45
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Just a Dream A song about a young couple marrying before the man goes off to war

21
117 52
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Paint Me a Birmingham A song about lost love and plans of a life that never came

The Best Country Songs About Home

22
100 43
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How Can I Help You Say Goodbye Patty Loveless - A song about life's many sad occassions

23
63 19
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RodPatrick added Blue Eyes Crying in the Rain Willie Nelson

24
65 22
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RodPatrick added The House That Built Me Miranda Lambert

25
95 45
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Coat of Many Colors Dolly Parton - A song about bullying and unkind children

26
95 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
123 69
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Jolene A song about a woman pleading to beuatiful Jolene not to steal her man.

28
53 17
Please Remember Me by Tim Mcgr... is listed (or ranked) 28 on the list The Saddest Country Songs

The Best Country Songs About Memories

29
76 36
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Wish You Were Here A song about a lover lost in a plane crash

30
77 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
75 37
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I’m No Stranger to the Rain The rain, that perfect and constant euphamism for sadness and lonliness.

32
80 41
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Your Cheatin' Heart Patsy Cline - A song about a cheating lover

33
61 26
You Should Be Here is listed (or ranked) 33 on the list The Saddest Country Songs
AidanBitterman added You Should Be Here

34
68 32
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erika-steen added The Little Girl John Michael Montgomery

35
80 44
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The Best I Ever Had A song about remembering a lost love.

The Druggiest Rock Stars of All Time

36
76 41
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The Baby A song about a son and his dying mother.

37
51 24
Colder Weather is listed (or ranked) 37 on the list The Saddest Country Songs
FireFront55 added Colder Weather

38
72 42
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God's Will A song about a terminally sick child

39
39 14
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DebbyHood added Don't Close Your Eyes Keith Whitley

40
54 27
Drink a Beer is listed (or ranked) 40 on the list The Saddest Country Songs
AidanBitterman added Drink a Beer

41
31 9
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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
41 19
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RodPatrick added I Told You So Randy Travis

Every Song in Newsies, Ranked by Singability

43
66 44
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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 38
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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
69 49
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Highway 20 Ride Zac Brown Band - A song about a man who must be away from his family.

46
60 42
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A Picture of Me (Without You) A devasted lover sings about life without his love.

47
60 44
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Today I Started Loving You Again A song about realizing love too late.

48
30 16
For the Good Times Ray Price is listed (or ranked) 48 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"  

49
24 11
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DebbyHood added Sing Me Back Home- Merle Haggard A man on death row  

50
33 20
I Sang Dixie Dwight Yoakam is listed (or ranked) 50 on the list The Saddest Country Songs
RodPatrick added I Sang Dixie Dwight Yoakam