Country Music The Saddest Country Songs  

Ranker Music
10.3k votes 1.4k voters 56.7k views 101 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
373 94
Ranker Video
Whiskey Lullaby Brad Paisley, Alison Krauss - A sad song about alcholosim and death.

2
356 89
Ranker Video
He Stopped Loving Her Today A song about a mans undying love for a woman

3
183 37
Remember When by Alan Jackson is listed (or ranked) 3 on the list The Saddest Country Songs

4
235 72
Ranker Video
If You're Reading This Based on a letter s fallen soldier writes home to his family.

5
201 64
Ranker Video
Go Rest High On That Mountain A song about the passing of a loved one

6
173 56
Ranker Video
I’m Already There A song about a lost loved one who is already in heaven.

7
223 83
Ranker Video
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
169 56
Ranker Video
If Heaven Wasn’t So Far Away A song about missing a grandfather who has passed away.

9
185 70
Ranker Video
I Drive Your Truck A song about a man who misses his buddy who has passed away.

10
164 59
Ranker Video
Alyssa Lies A sad song about a little girl who is a victim of abuse.

11
109 28
Ranker Video
RodPatrick added Hurt Johnny Cash

12
187 79
Ranker Video
What Hurts the Most A song about wondering what could have been

13
158 63
Ranker Video
Concrete Angel A song about a forgotten little girl who has to take care of herself.

14
132 49
Ranker Video
Holes in the Floor of Heaven Another sad song about loss, love and life

15
127 46
Ranker Video
I'm So Lonesome I Could Cry Johnny Cash - The title says it all

16
119 45
Ranker Video
Always on My Mind Willie Nelson - A song about regrets and unforgettable love.

17
129 53
Ranker Video
American Soldier Toby Keith - A song about soldiers who must go off to fight.

18
133 56
Ranker Video
Travelin' Soldier Dixie Chicks - A song about a soldier who doesn't come home

19
96 33
Ranker Video
jeremy-fisher added Don't Laugh at Me Mark Wills

20
114 47
Ranker Video
Just a Dream A song about a young couple marrying before the man goes off to war

21
122 54
Ranker Video
Paint Me a Birmingham A song about lost love and plans of a life that never came

22
69 20
Ranker Video
RodPatrick added Blue Eyes Crying in the Rain Willie Nelson

23
73 24
Ranker Video
RodPatrick added The House That Built Me Miranda Lambert

24
102 45
Ranker Video
How Can I Help You Say Goodbye Patty Loveless - A song about life's many sad occassions

25
101 47
Ranker Video
When I Call Your Name Vince Gill - A sad song about a man finding his wife has left him.

26
98 47
Ranker Video
Coat of Many Colors Dolly Parton - A song about bullying and unkind children

27
59 19
Please Remember Me by Tim Mcgr... is listed (or ranked) 27 on the list The Saddest Country Songs

28
126 71
Ranker Video
Jolene A song about a woman pleading to beuatiful Jolene not to steal her man.

29
82 38
Ranker Video
I’m No Stranger to the Rain The rain, that perfect and constant euphamism for sadness and lonliness.

30
80 37
Ranker Video
Wish You Were Here A song about a lover lost in a plane crash

31
82 39
Ranker Video
Help Me Make It Through the Night A sad song about a night of love that shouldn't have been

32
85 42
Ranker Video
Your Cheatin' Heart Patsy Cline - A song about a cheating lover

33
71 33
Ranker Video
erika-steen added The Little Girl John Michael Montgomery

34
46 15
Ranker Video
DebbyHood added Don't Close Your Eyes Keith Whitley

35
84 47
Ranker Video
The Best I Ever Had A song about remembering a lost love.

36
62 29
You Should Be Here is listed (or ranked) 36 on the list The Saddest Country Songs
AidanBitterman added You Should Be Here

37
79 43
Ranker Video
The Baby A song about a son and his dying mother.

38
37 10
Ranker Video
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."

39
56 26
Colder Weather is listed (or ranked) 39 on the list The Saddest Country Songs
FireFront55 added Colder Weather

40
58 29
Drink a Beer is listed (or ranked) 40 on the list The Saddest Country Songs
AidanBitterman added Drink a Beer

41
47 20
Ranker Video
RodPatrick added I Told You So Randy Travis

42
74 44
Ranker Video
God's Will A song about a terminally sick child

43
67 42
Ranker Video
A Picture of Me (Without You) A devasted lover sings about life without his love.

44
69 46
Ranker Video
Don’t It Make My Brown Eyes Blue It's right there in the title, this is a song for crying.

45
37 18
For the Good Times Ray Price is listed (or ranked) 45 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"  

46
61 41
Ranker Video
I’m Gonna Love You Through It A song about loving and caring for someone through their battle with cancer.

47
66 46
Ranker Video
Today I Started Loving You Again A song about realizing love too late.

48
70 51
Ranker Video
Highway 20 Ride Zac Brown Band - A song about a man who must be away from his family.

49
29 12
Ranker Video
DebbyHood added Sing Me Back Home- Merle Haggard A man on death row  

50
38 22
I Sang Dixie Dwight Yoakam is listed (or ranked) 50 on the list The Saddest Country Songs
RodPatrick added I Sang Dixie Dwight Yoakam