country music The Saddest Country Songs  

Ranker Music
7.2k votes 963 voters 45.3k views 99 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
267 66
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Whiskey Lullaby Brad Paisley, Alison Krauss - A sad song about alcholosim and death.

2
246 58
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He Stopped Loving Her Today A song about a mans undying love for a woman

3
158 47
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If You're Reading This Based on a letter s fallen soldier writes home to his family.

4
82 15
Remember When by Alan Jackson is listed (or ranked) 4 on the list The Saddest Country Songs

5
135 48
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I Drive Your Truck A song about a man who misses his buddy who has passed away.

6
151 59
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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'

7
124 45
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Alyssa Lies A sad song about a little girl who is a victim of abuse.

8
107 37
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If Heaven Wasn’t So Far Away A song about missing a grandfather who has passed away.

9
143 61
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What Hurts the Most A song about wondering what could have been

10
125 50
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Go Rest High On That Mountain A song about the passing of a loved one

11
108 40
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I’m Already There A song about a lost loved one who is already in heaven.

12
99 37
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Holes in the Floor of Heaven Another sad song about loss, love and life

13
110 48
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Concrete Angel A song about a forgotten little girl who has to take care of herself.

14
71 24
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jeremy-fisher added Don't Laugh at Me Mark Wills

The Best Country Songs About Gambling

15
91 38
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I'm So Lonesome I Could Cry Johnny Cash - The title says it all

16
96 42
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American Soldier Toby Keith - A song about soldiers who must go off to fight.

17
50 11
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RodPatrick added Hurt Johnny Cash

18
94 43
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Paint Me a Birmingham A song about lost love and plans of a life that never came

19
86 38
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Always on My Mind Willie Nelson - A song about regrets and unforgettable love.

20
86 39
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Just a Dream A song about a young couple marrying before the man goes off to war

21
95 47
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Travelin' Soldier Dixie Chicks - A song about a soldier who doesn't come home

The Best Opening Act You've Ever Seen

22
101 55
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Jolene A song about a woman pleading to beuatiful Jolene not to steal her man.

23
80 39
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When I Call Your Name Vince Gill - A sad song about a man finding his wife has left him.

24
74 35
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How Can I Help You Say Goodbye Patty Loveless - A song about life's many sad occassions

25
77 39
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Coat of Many Colors Dolly Parton - A song about bullying and unkind children

26
61 28
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Wish You Were Here A song about a lover lost in a plane crash

27
38 11
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RodPatrick added Blue Eyes Crying in the Rain Willie Nelson

28
38 12
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RodPatrick added The House That Built Me Miranda Lambert

The Best Country Songs About Women

29
62 32
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Help Me Make It Through the Night A sad song about a night of love that shouldn't have been

30
65 35
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Your Cheatin' Heart Patsy Cline - A song about a cheating lover

31
60 33
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The Baby A song about a son and his dying mother.

32
39 16
You Should Be Here is listed (or ranked) 32 on the list The Saddest Country Songs
AidanBitterman added You Should Be Here

33
40 17
Drink a Beer is listed (or ranked) 33 on the list The Saddest Country Songs
AidanBitterman added Drink a Beer

34
63 37
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The Best I Ever Had A song about remembering a lost love.

35
56 31
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I’m No Stranger to the Rain The rain, that perfect and constant euphamism for sadness and lonliness.

The 37 Greatest On-Stage Falls of All Time

36
37 15
Colder Weather is listed (or ranked) 36 on the list The Saddest Country Songs
FireFront55 added Colder Weather

37
49 26
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erika-steen added The Little Girl John Michael Montgomery

38
30 10
Please Remember Me by Tim Mcgr... is listed (or ranked) 38 on the list The Saddest Country Songs

39
55 36
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God's Will A song about a terminally sick child

40
29 13
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RodPatrick added I Told You So Randy Travis

41
55 38
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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.

42
46 32
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I’m Gonna Love You Through It A song about loving and caring for someone through their battle with cancer.

The Best Country Songs About Memories

43
56 42
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Highway 20 Ride Zac Brown Band - A song about a man who must be away from his family.

44
46 33
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Love,Me A song about lover's trying to be together whatever the consewuences.

45
15 3
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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."

46
44 36
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A Picture of Me (Without You) A devasted lover sings about life without his love.

47
13 4
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DebbyHood added Sing Me Back Home- Merle Haggard A man on death row  

48
45 38
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Today I Started Loving You Again A song about realizing love too late.

49
23 16
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hejacountrybest added Daryle Worley — Miss My Friend

50
13 6
For the Good Times Ray Price is listed (or ranked) 50 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"