country music The Saddest Country Songs  

Ranker Music
8.2k votes 1.1k voters 49.2k 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
305 76
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Whiskey Lullaby Brad Paisley, Alison Krauss - A sad song about alcholosim and death.

2
274 68
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He Stopped Loving Her Today A song about a mans undying love for a woman

3
186 53
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If You're Reading This Based on a letter s fallen soldier writes home to his family.

4
108 22
Remember When by Alan Jackson is listed (or ranked) 4 on the list The Saddest Country Songs

5
146 53
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Go Rest High On That Mountain A song about the passing of a loved one

6
172 68
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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
154 59
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I Drive Your Truck A song about a man who misses his buddy who has passed away.

8
126 43
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I’m Already There A song about a lost loved one who is already in heaven.

9
126 43
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If Heaven Wasn’t So Far Away A song about missing a grandfather who has passed away.

10
138 51
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Alyssa Lies A sad song about a little girl who is a victim of abuse.

11
161 70
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What Hurts the Most A song about wondering what could have been

12
70 16
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RodPatrick added Hurt Johnny Cash

13
128 54
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Concrete Angel A song about a forgotten little girl who has to take care of herself.

14
109 43
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Holes in the Floor of Heaven Another sad song about loss, love and life

Mythical Creatures That Were Found in Real Life

15
99 42
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I'm So Lonesome I Could Cry Johnny Cash - The title says it all

16
96 40
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Always on My Mind Willie Nelson - A song about regrets and unforgettable love.

17
98 43
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Just a Dream A song about a young couple marrying before the man goes off to war

18
105 48
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Paint Me a Birmingham A song about lost love and plans of a life that never came

19
104 48
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American Soldier Toby Keith - A song about soldiers who must go off to fight.

20
77 30
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jeremy-fisher added Don't Laugh at Me Mark Wills

21
107 52
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Travelin' Soldier Dixie Chicks - A song about a soldier who doesn't come home

Great Country Songs About Falling in Love

22
84 39
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How Can I Help You Say Goodbye Patty Loveless - A song about life's many sad occassions

23
70 32
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Wish You Were Here A song about a lover lost in a plane crash

24
53 19
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RodPatrick added The House That Built Me Miranda Lambert

25
85 44
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When I Call Your Name Vince Gill - A sad song about a man finding his wife has left him.

26
110 64
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Jolene A song about a woman pleading to beuatiful Jolene not to steal her man.

27
81 42
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Coat of Many Colors Dolly Parton - A song about bullying and unkind children

28
44 15
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RodPatrick added Blue Eyes Crying in the Rain Willie Nelson

The Best Country Songs About Gambling

29
70 38
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Your Cheatin' Heart Patsy Cline - A song about a cheating lover

30
50 22
You Should Be Here is listed (or ranked) 30 on the list The Saddest Country Songs
AidanBitterman added You Should Be Here

31
40 14
Please Remember Me by Tim Mcgr... is listed (or ranked) 31 on the list The Saddest Country Songs

32
46 19
Colder Weather is listed (or ranked) 32 on the list The Saddest Country Songs
FireFront55 added Colder Weather

33
58 29
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erika-steen added The Little Girl John Michael Montgomery

34
65 35
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Help Me Make It Through the Night A sad song about a night of love that shouldn't have been

35
50 23
Drink a Beer is listed (or ranked) 35 on the list The Saddest Country Songs
AidanBitterman added Drink a Beer

The Best Rappers of the 2000s

36
62 34
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I’m No Stranger to the Rain The rain, that perfect and constant euphamism for sadness and lonliness.

37
70 42
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The Best I Ever Had A song about remembering a lost love.

38
65 39
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The Baby A song about a son and his dying mother.

39
63 39
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God's Will A song about a terminally sick child

40
33 16
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RodPatrick added I Told You So Randy Travis

41
64 45
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Highway 20 Ride Zac Brown Band - A song about a man who must be away from his family.

42
53 35
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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 Songs on Nas's Album Illmatic

43
59 41
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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
20 6
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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."

45
52 38
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Love,Me A song about lover's trying to be together whatever the consewuences.

46
49 40
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A Picture of Me (Without You) A devasted lover sings about life without his love.

47
48 41
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Today I Started Loving You Again A song about realizing love too late.

48
16 8
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DebbyHood added Sing Me Back Home- Merle Haggard A man on death row  

49
23 16
I Sang Dixie Dwight Yoakam is listed (or ranked) 49 on the list The Saddest Country Songs
RodPatrick added I Sang Dixie Dwight Yoakam

50
18 11
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DebbyHood added Don't Close Your Eyes Keith Whitley