Country's 20 Saddest Songs of All Time

Tearjerkers Are the Genre's Trademark

Country music has developed a reputation as the designated genre for sad songs. While it's not the only theme country music explores, it's certainly one the genre has mastered. Country artists have recorded hundreds of poignant tearjerkers throughout the years. Here are the 20 saddest country songs of all time.

20
of 20

Sammi Smith: 'Help Me Make It Through the Night'

Sammi Smith
Michael Ochs Archives / Getty Images

The woman sings about spending the night with a man. It's not said outright, but the lyrics imply that they may be having an affair. She doesn't care what's right or wrong. All she needs is a friend.

Lyrics:

"Yesterday is dead and gone / And tomorrow's out of sight / And it's sad to be alone / Help me make it through the night."

Song Info:

  • Released in 1970
  • Peaked at No. 1 on the country charts; No. 8 on the pop charts
  • From the album ​"Help Me Make It Through the Night"
  • One of the most successful country singles of all time
  • Originally written and recorded by country artist Kris Kristofferson

Download/Purchase "Help Me Make It Through the Night"

19
of 20

Bryan White: 'Someone Else's Star'

Bryan White - Bryan White
Asylum

The guy in this song is alone and wishing he could find his true love. He feels that maybe he's wishing on someone else's star because good things happen for others, but not for him.

Lyrics:

"I guess I must be wishing on / Someone else's star / It seems like someone else keeps getting /  What I'm wishing for / Why can't I be as lucky / As those other people are / I guess I must be wishing / On someone else's star."

Song Info:

  • Released in 1995
  • Peaked at No. 1 on the country charts
  • From the album ​"Bryan White"

Download/Purchase "Someone Else's Star"

18
of 20

Vince Gill: 'Go Rest High on That Mountain'

Vince Gill - When Love Finds You
MCA Nashville

 

This song is a tribute Vince Gill wrote for both the late country artist Keith Whitley, who died in 1989, and Gill's brother, who died in 1993. Patty Loveless and Ricky Skaggs provide vocals. Note the "no stranger to the rain" line. "I'm No Stranger to the Rain" is a Whitley song.

Lyrics:

"Go rest high on that mountain / Son, your work on earth is done / Go to heaven a shoutin' / Love for the Father and Son."

Song Info:

  • Released in 1995
  • Peaked at No. 14 on the country charts
  • From the album  "When Love Finds You"
  • Won the 1996 Country Music Association Song of the Year award and two Grammy Awards for Best Male Country Vocal Performance and Best Country Song

Download/Purchase "Go Rest High on That Mountain"

17
of 20

Steve Wariner: 'Holes in the Floor of Heaven'

Steve Wariner - Burnin' the Roadhouse Down
Capitol Nashville

 

We witness three different events in a young man's life as he loses his grandmother just before he turns 8, loses his wife, and then, at his daughter's wedding, misses his wife. All three times it rains, and we're told these are tears from the loved ones who wish they were with us.

Lyrics:

"And there's holes in the floor of heaven / And her tears are pouring down / That's how you know she's watching / Wishing she could be here now."

Song Info:

  • Released in 1998
  • Peaked at No. 2 on the country charts
  • From the album ​"Burnin' the Roadhouse Down"
  • Named 1998's Song of the Year by both the Country Music Association and the Academy of Country Music

Download/Purchase the "Holes In the Floor of Heaven"

16
of 20

Hank Williams: 'Your Cheatin' Heart'

Hank Williams
GAB Archive / Redferns / Getty Images

The singer is singing to his cheating girlfriend, saying that her cheating heart is going to tell on her.

Lyrics:

"Your cheatin' heart will make you weep / You'll cry and cry and try to sleep / But sleep won't come the whole night through / Your cheatin' heart will tell on you."

Song Info:

  • Released as a single in 1953
  • Peaked at No. 1 on the country charts
  • Recorded during Hank Williams' last studio session before his death in January 1953
  • Noted as the song that defines country music

Download/Purchase "Your Cheatin' Heart"

15
of 20

Martina McBride: 'God's Will'

Martina McBride - Martina
RCA Nashville

This song tells the story of a young boy who wears braces on his legs. He may have problems with mobility, but he has no problem at all with his big heart. Toward the end of the song, you learn the boy isn't expected to live, and whether he makes it when they move to California goes unanswered.

Lyrics:

"And I never got to tell her that the boy showed me the truth / 
In crayon red, on notebook paper, he'd written 'Me and God love you.'"

Song Info:

Download/Purchase "God's Will"

14
of 20

Collin Raye: 'Love, Me'

Collin Raye - All I Can Be
Epic

A young boy finds out that his grandmother's father didn't approve of his grandfather and tried to keep them apart. The couple had planned to run away and get married, but instead of finding his grandmother waiting, he found a note telling him not to give up on her.

Lyrics:

"If you get there before I do, don't give up on me / I'll meet you when my chores are through / I don't know how long I'll be / But I'm not gonna let you down, darling wait and see / And between now and then, till I see you again / I'll be loving you / Love, me."

Song Info:

  • Released in 1991
  • Peaked at No. 1 on the country charts
  • From the album ​"All I Can Be"

Download/Purchase "Love, Me"

13
of 20

Tracy Lawrence: 'Paint Me a Birmingham'

Tracy Lawrence - Strong
Dreamworks

A man encounters a painter on the beach and asks if he only paints ocean scenes. The man says for $20 he can paint anything. He asks him to paint a picture of the plans he had with his lost love.

Lyrics:

"Could you paint me a Birmingham / Make it look just the way I plan / A little house on the edge of town / Porch going all the way around / Put her there on the front yard swing / Cotton dress, make it early spring / For a while she'll be mine again / If you could paint me a Birmingham."

Song Info:

  • Released in 2004
  • Peaked at No. 4 on the country charts
  • From the album ​"Strong"

Download/Purchase "Paint Me a Birmingham"

12
of 20

Mark Wills: 'Wish You Were Here'

Mark Wills - Wish You Were Here
Mercury Nashville

A man takes a plane trip and tells his wife he'll talk to her that night. Instead, she receives a call saying the plane went down and there are no survivors. Later, she receives a postcard that says "heaven" on it and his words, that he wishes she were there.

Lyrics:

"Wish you were here, wish you could see this place / Wish you were near, I wish I could touch your face / The weather's nice, it's paradise / It's summertime all year and there's some folks we know / They say, "Hello", I miss you so, wish you were here."

Song Info:

  • Released in 1999
  • Peaked at No. 1 on the country charts
  • From the album "Wish You Were Here"

Download/Purchase "Wish You Were Here"

11
of 20

George Jones: 'A Picture of Me (Without You)'

George Jones - Essential George Jones
Legacy

The man in this song is just devastated to be without the woman he loves. He compares his world to a garden where nothing is growing and a river where nothing is flowing.

Lyrics:

"Imagine a world where no music was playing / Then think of a church where nobody's praying / If you've ever looked up at a sky with no blue / Then you've seen a picture of me without you."

Song Info:

  • Released in 1972
  • Peaked at No. 5 on the country charts
  • From the album ​"A Picture of Me (Without You)"

Download/Purchase "A Picture of Me (Without You)"

10
of 20

Carrie Underwood: 'Just a Dream'

Carrie Underwood - Carnival Ride
Arista Nashville / Sony BMG

This song is about a young couple who marry just before the husband has to go off to war. They have lots of plans for their life together, but none of it comes to be -- the husband is killed in the war. So very sad; an incredible video goes with the song.

Lyrics:

 "Baby, why'd you leave me, why'd you have to go? / I was counting on forever, now I'll never know / I can't even breathe." 

Song Info:

  • Released in 2008
  • Peaked at No. 1 on the country charts
  • From the album ​"Carnival Ride"
  • Watch the music video

Download/Purchase "Just a Dream"

09
of 20

Brad Paisley and Alison Krauss: 'Whiskey Lullaby'

Brad Paisley - Mud on the Tires
Arista Nashville

A tale of alcoholism, adultery and death. A woman cheats on her husband, and he catches the pair and leaves her. He drinks himself to death, and her guilt causes her to do the same.

Lyrics:

"He put that bottle to his head and pulled the trigger / And finally drank away her memory / Life is short, but this time it was bigger / Than the strength he had to get up of his knees."

Song Info:

  • Released in 2004
  • Peaked at No. 3 on the country charts
  • From the album ​"Mud on the Tires"
  • Won both Song of the Year and Video of the Year at the 2004 Country Music Association Awards and the Academy of Country Music Awards
  • Certified 2x platinum

Download/Purchase "Whiskey Lullaby"

08
of 20

Kathy Mattea: 'Where've You Been'

Kathy Mattea - Willow in the Wind
Island Def Jam

Claire finds the man of her dreams in Edwin. They marry and she becomes a salesman's wife. When he's gone, she isn't the same. In the end, they're in the hospital on separate floors, and she no longer remembers anyone until they wheel him in, and she again asks him "Where've you been? I'm not myself when you're away."

Lyrics:

"Where've you been? / I've looked for you forever and a day / Where've you been? / I'm just not myself when you're away."

Song Info:

  • Released in 1989
  • Peaked at No. 10 on the country charts
  • From the album ​"Willow in the Wind"
  • Named Best Female Country Performance at the 1991 Grammy Awards

Download/Purchase "Where've You Been"

 

07
of 20

Tim McGraw: 'If You're Reading This'

Tim McGraw - Let It Go
Curb Records

This song is based on a letter written by a soldier going off to war that will be sent to his family if he doesn't come back. In it he tells his wife how much he wishes he could give her one more kiss, and he's sorry he won't get to see their little girl.

Lyrics:

"If you're reading this halfway around the world / I won't be there to see the birth of our little girl."

Song Info:

  • Released as a live recording in 2007 after Tim McGraw's performance of the song at the Academy of Country Music Awards
  • Peaked at No. 3 on the country charts
  • From the album ​"Let It Go"

Download/Purchase "If You're Reading This"

06
of 20

Jason Michael Carroll: 'Alyssa Lies'

Jason Michael Carroll - Waitin' in the Country
Sony BMG / Arista Nashville

In this song, a little girl tells her father about her schoolmate who lies at school. It turns out the young girl is a victim of abuse and hides her bruises from her classmates and teachers.As in Martina McBride's song "Concrete Angel," it's too late to save the girl.

Lyrics:

"She doesn't lie in the classroom / She doesn't lie anymore at school / Alyssa lies with Jesus / Because there's nothing anyone would do."

Song Info:

  • Released in 2006
  • Peaked at No. 5 on the country charts
  • From the album ​"Waitin' in the Country"
  • It took Jason Michael Carroll a year and a half to write the lyrics

Download/Purchase "Alyssa Lies"

 

05
of 20

Blake Shelton: 'The Baby'

Blake Shelton - The Dreamer
Warner Nashville

 

This is a story of a man, the baby of the family, who finds out that his mother is severely ill and will probably not make it through the night. He's out of town, but he rushes home to be by her side, only to arrive too late.

Lyrics:

"She looked like she was sleepin' / And my family had been weepin' / By the time that I got to her side / And I knew that she'd been taken / And my heart it was breakin' / I never got to say goodbye."

Song Info:

  • Released in 2002
  • Peaked at No. 1 on the country charts
  • From the album ​"The Dreamer"
  • Watch the music video

Download/Purchase "The Baby"

04
of 20

Martina McBride: 'Concrete Angel'

Martina McBride - Greatest Hits
RCA Nashville

This is a sad song about a little girl who has to take care of herself. She packs her own lunch and picks out her clothes for school. Even though she displays bruises, no one dares to think she may be abused until it's too late.

Lyrics:

"A statue stands in a shaded place / An angel girl with an upturned face / A name is written on a polished rock / A broken heart that the world forgot."

Song Info:

  • Released in 2002
  • Peaked at No. 5 on the country charts
  • From the album ​"Greatest Hits"
  • Watch the music video

Download/Purchase "Concrete Angel"

03
of 20

Joe Nichols: 'I'll Wait for You'

Joe Nichols - III
Universal South

This song is about a couple; the husband travels a lot and always seems to be late coming home. When the wife is seriously ill in the hospital, the husband is out of town, so he rents a car and drives home. He makes it home too late, and the doctor hands him a note from his wife saying she'll wait for him.

Lyrics:

"And it said 'I'll wait for you at Heaven's gate / Oh I don't care how long it takes / And I'll tell Saint Pete I can't come in / Without my love and my best friend, Oh this ain't nothing new / Sweetheart, I'll wait for you.'"

Song Info:

Download/Purchase "I'll Wait For You"

02
of 20

Patty Loveless: 'How Can I Help You Say Goodbye'

Patty Loveless - Only What I Feel
Epic

This song deals with three specific sad occasions in the storyteller's life: moving away from her best friend, a marriage ending in divorce and the loss of her mother. It doesn't get any sadder than this.

Lyrics:

"And with her final word, she tried to help me understand / Mama whispered softly, Time will ease your pain / Life's about changing, nothing ever stays the same."

Song Info:

  • Released in 1993
  • Peaked at No. 3 on the country charts
  • From the album ​"Only What I Feel"

Download/Purchase "How Can I Help You Say Goodbye"

01
of 20

George Jones: 'He Stopped Loving Her Today'

George Jones - I Am What I Am
Epic

This song is about a man's love for a woman, even after they break up. He loved her until the day he died.

Lyrics:

"He stopped loving her today / They placed a wreath upon his door / Soon they'll carry him away / He stopped loving her today."

Song Info:

  • Released in 1980
  • Peaked at No. 1 on the country charts
  • From the album ​"I Am What I Am"
  • Consistently named the greatest country song of all time
  • Won the 1980 Grammy Award for Best Male Country Vocal Performance; the 1980 Academy of Country Music Award for Song of the Year; and the 1980 and 1981 Country Music Association Award for Song of the Year

Download/Purchase "He Stopped Loving Her Today"