Country Music The Saddest Country Songs  

Ranker Music
9.7k votes 1.3k voters 54.4k 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.

344 80
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He Stopped Loving Her Today A song about a mans undying love for a woman

352 90
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Whiskey Lullaby Brad Paisley, Alison Krauss - A sad song about alcholosim and death.

166 36
Remember When by Alan Jackson is listed (or ranked) 3 on the list The Saddest Country Songs

229 67
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If You're Reading This Based on a letter s fallen soldier writes home to his family.

188 63
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Go Rest High On That Mountain A song about the passing of a loved one

212 77
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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'

164 53
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I’m Already There A song about a lost loved one who is already in heaven.

161 53
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If Heaven Wasn’t So Far Away A song about missing a grandfather who has passed away.

159 57
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Alyssa Lies A sad song about a little girl who is a victim of abuse.

99 25
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RodPatrick added Hurt Johnny Cash

173 68
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I Drive Your Truck A song about a man who misses his buddy who has passed away.

180 75
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What Hurts the Most A song about wondering what could have been

151 59
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Concrete Angel A song about a forgotten little girl who has to take care of herself.

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

The Best Country Songs for Weddings

124 48
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Holes in the Floor of Heaven Another sad song about loss, love and life

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

123 52
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American Soldier Toby Keith - A song about soldiers who must go off to fight.

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

126 55
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Travelin' Soldier Dixie Chicks - A song about a soldier who doesn't come home

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

117 51
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Paint Me a Birmingham A song about lost love and plans of a life that never came

The Best Concert Movies Streaming on Hulu

98 43
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How Can I Help You Say Goodbye Patty Loveless - A song about life's many sad occassions

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

64 22
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RodPatrick added The House That Built Me Miranda Lambert

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

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.

122 69
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Jolene A song about a woman pleading to beuatiful Jolene not to steal her man.

52 17
Please Remember Me by Tim Mcgr... is listed (or ranked) 28 on the list The Saddest Country Songs

The Best Country Songs About Work

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

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

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

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

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

60 26
You Should Be Here is listed (or ranked) 34 on the list The Saddest Country Songs
AidanBitterman added You Should Be Here

80 43
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The Best I Ever Had A song about remembering a lost love.

16 Songs That Don't Mean What You Think They Do

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

54 26
Drink a Beer is listed (or ranked) 37 on the list The Saddest Country Songs
AidanBitterman added Drink a Beer

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

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

50 24
Colder Weather is listed (or ranked) 40 on the list The Saddest Country Songs
FireFront55 added Colder Weather

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."

41 19
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RodPatrick added I Told You So Randy Travis

The Best Country Songs About Food

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.

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.

68 49
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Highway 20 Ride Zac Brown Band - A song about a man who must be away from his family.

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

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

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"  

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

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