The 50 Saddest 90s Country Songs That Make You Cry

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The 50 Saddest 90s Country Songs That Make You Cry

Some of the best sad music comes from 90s country songs. 

Sometimes we can all use a good cry to let out our emotions. And what better way than listening to some songs that make you cry?

Take yourself back and find comfort in the timeless themes of these 50 saddest 90s country songs that make you cry. 

RELATED: 16 Sweet Love Quotes From Classic Country Music Song Lyrics​

If you love country music, you’re familiar with the genre’s tendency to make you cry. 

1. Holes in the Floor of Heaven (Steve Wariner)

This song stresses the belief that the rain symbolizes the tears of the protagonist’s grandmother and wife who passed away. 

“Cause 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.”

2. Anymore (Travis Tritt)

The lyrics of this song illustrate the pain of heartbreak and unrequited love. 

“My tears no longer waiting. My resistance ain’t that strong. My mind keeps recreating a love with you alone and I’m tired of pretending I don’t love you anymore.”

3. Where Do I Fit in the Picture (Clay Walker)

Walker depicts the emotions of shifting apart from a past lover and wondering where all the history has gone. 

“But where do I fit in the picture or do I really fit at all or have I become a fixture on an old forgotten wall?”

4. It Matters to Me (Faith Hill)

Have you ever felt like you care more than your partner? So has Faith Hill in this song that explains miscommunication and inconsistencies in relationships. 

“When we don’t talk, when we don’t touch, when it doesn’t feel like we’re even in love, it matters to me.”

5. You Were Mine (The Chicks)

With this sad song, The Chicks bring to life the heartbreak of divorce and the subsequent difficulty of having children together. 

“I took out all the pictures of our wedding day. It was a time of love and laughter, happy ever after but even those old pictures have begun to fade.” 

6. All the Good Ones Are Gone (Pam Tillis)

Written in third person, Tillis sings about a 34-year-old woman who is hopeless in love, feeling that there are no good men for her. 

“And her mama called this morning, said I’m worried about my baby. I wish you had a family of your own. She said mom it’s not that easy.” 

7. Feed Jake (Pirates of the Mississippi)

This song mentions the stereotypes of the music industry, homelessness, and homosexuality while being humble by the writer’s dog, Jake. 

“Now I lay me down to sleep and pray the Lord my soul to keep. If I die before I wake, feed Jake.”

8. I Don’t Call Him Daddy (Doug Supernaw)

Supernaw gives the viewpoint of a divorced father whose son is being surrounded by the presence of another father figure — his mother’s new boyfriend. 

“Oh, don’t worry dad, you know, it don’t matter what we do cause I don’t call him daddy, he can never be like you.” 

9. Sweet Old World (Lucinda Williams)

Dedicated to a loved one who committed suicide, Williams wonders if they ever noticed the beauty of living. 

“Someone calling your name, somebody so warm cradled in your arm. Didn’t you think you were worth anything? See what you lost when you left this world, this sweet old world.” 

10. Go Rest High on That Mountain (Vince Gill)

Gill was influenced by the death of country artist Keith Whitley and his brother to write this song about finding closure after grief. 

“Go rest high on that mountain son, your work on earth is done. Go to heaven a-shoutin’ love for the Father and the Son.” 

11. She Thinks His Name Was John (Reba McEntire)

This song is about a woman’s one-night stand that leads to her contracting the AIDS virus. As a result, she begins to mourn the loss of key elements to life such as marriage and motherhood. 

“Now each day is one day that’s left in her life. She won’t know love, have a marriage or sing lullabies. She lays alone and cries herself to sleep cause she let a stranger kill her hopes and her dreams.” 

12. Don’t Take the Girl (Tim McGraw)

Telling a story of two lovers, McGraw sings about their struggles with different stages of life and how the man ultimately does what he can to make sure no one takes his girl. 

“Take the very breath you gave me. Take the heart from my chest. I’ll gladly take her place if you’ll let me. Make this my last request.”

13. Butterfly Kisses (Bob Carlisle)

Bob Carlisle wrote this song for his daughter on her 16th birthday as an ode to their relationship together. 

“All the precious time. Like the wind, the years go by. Precious butterfly. Spread your wings and fly.”

14. The Song Remembers When (Trisha Yearwood)

The song about a song — Yearwood sings about the memories that get brought up when the protagonist hears a song that reminds her of a past lover. 

“I guess something must have happened and we must have said goodbye. And my heart must have been broken though I can’t recall just why.”

15. It’s Your Song (Garth Brooks)

In a dedication to his mother, Brooks sings this song about the love and support she gave him throughout his career. 

“It was your song that made me sing and it was your voice that gave me wings and it was your light that shined.”

16. Who’s That Man (Toby Keith)

This song is about a man who returns to his home-town and sees his ex-wife, children, and family dog with a father-figure in the picture. 

“I planted that tree out by the fence not long after we moved in. That’s my kids and that’s my wife, who’s that man runnin’ my life.”

17. The Fool (Lee Ann Womack)

A woman comes face-to-face with her partner’s ex, who he is still in love with. Womack sings of the heartbreak in knowing he’s not over the past. 

“But you hold his heart in the palm of your hand and it’s breaking mine in two. Cause I’m the fool in love with the fool who’s still in love with you.”

18. A House With No Curtains (Alan Jackson)

Despite trying to keep their relationships struggles hidden, those around this couple in the song are aware that neither person is happy. 

“We could pack up and leave in different directions if we just had somewhere to go. We just keep pretending afraid of the ending, admitting what everyone knows.”

19. You Don’t Even Know Who I Am (Patty Loveless)

This song gives insight to both sides of a divorce, explaining their realizations that they have become strangers over time. 

“It said, you don’t even know who I am. You left me a long time ago. You don’t even know who I am so what do you care if I go?”

20. What Mattered Most (Ty Herndon)

After the relationship ended, the man in the song admits that it was his fault for not paying attention to his girlfriend’s inner self. 

“I thought I knew the girl so well. If she was sad I couldn’t tell. I missed the point. I missed the signs. So if she’s gone the fault is mine.”

21. I Can’t Do That Anymore (Faith Hill)

This song comes from a female narrator who has given up her career in order to uphold chores and satisfy her husband until she demands a life of her own. 

“I keep on giving but I can’t stop living. A woman needs a little something of her own. I like happy endings.”

22. Can’t Really Be Gone (Tim McGraw)

After he is left by his partner, the protagonist is in disbelief that she could really be gone if she has left behind personal belongings. 

“Her book is lying on the bed, the two of hearts to mark her page. Now who could ever walk away with so much left undone so she can’t really be gone.”

23. Someone Else’s Star (Bryan White)

This song is about a man who’s just looking for love and can’t seem to find it, believing that he might be wishing on another person’s star. 

“Everywhere I look it’s lovers that I see. Seems like everyone’s in love with everyone but me.”

24. The Car (Jeff Carson)

Carson sings about a father-son relationship that centers around a Ford Mustang until the father dies and leaves his son with the car. 

“It’s not the car you’re needin’ but it’s my chance to be with you. I hope you understand I always did the best that I could do.” 

25. Love, Me (Collin Raye)

The narrator tells the love story of his grandparents and their ever-evolving promise to always love each other. 

“But I’m not gonna let you down, darling wait and see. And between now and then, ‘til I see you again I’ll be loving you. Love, me.”

RELATED: 30 Kenny Rogers Quotes About Life, Fame & Country Music​

26. The Walk (Sawyer Brown)

This song is about the different walks of life and the connection between a father and son throughout these stages. 

“So dry eyes I understand just what you’re goin’ through cause I took this same walk with my old man. Boy, I’ve been in your shoes.”

27. Wish You Were Here (Mark Wills)

Playing upon the irony of a postcard being sent from heaven after the death of her lover, this song offers a positive outlook on life after death. 

“She got a call that night but it wasn’t from him. It didn’t sink in right away, ma’am the plane went down. Our crews have searched the ground. No survivors found she heard him say.”

28. Today My World Slipped Away (George Strait)

This song describes the way a man feels after his divorce is finalized. It depicts his heartache, confusion, and disappointment. 

“We buried the plans that we made and tonight I’m alone and afraid cause today my world slipped away.”

29. If You Came Back From Heaven (Lorrie Morgan)

Morgan sings of a woman’s desire to have her lover back in her life again, wondering what it would be like if God gave him back from heaven. 

“Oh, if you came back from heaven would it be like it was then? Could we just pick up where we left off and try it all again?”

30. When She Cries (Restless Heart)

In this song, a man battles with not knowing how to be there for his lover like she is for him, even though her tears break his heart. 

“When she cries at night and she doesn’t think I can hear her, she tries to hide all the fear she feels inside.”

31. How Can I Help You Say Goodbye (Patty Loveless)

Loveless speaks to the mother-daughter relationship as the narrator’s mother is comforting during her most difficult times. 

“Sitting with mama alone in her bedroom, she opened her eyes and then squeezed my hand. She said I have to go now my time here is over.”

32. Don’t Laugh at Me (Mark Wills)

This song has been an inspiration to many with its relatable theme of being picked on. Wills sings of children and homeless men who are only asking for acceptance. 

“A little girl who never smiles cause I’ve got braces on my teeth. And I know how it feels to cry myself to sleep.”

33. Please Remember Me (Tim McGraw)

A failed relationship makes this protagonist realize he wasn’t what his girlfriend needed, but still hopes to be remembered. 

“You’ll find better love, strong as it ever was. Deep as the river runs, warm as the morning sun. Please remember me.”

34. Passionate Kisses (Mary Chapin Carpenter)

The female narrator ponders her desires and ambitions, becoming frustrated with how little she is asking for. 

“Do I want too much? Am I going overboard to want that touch? I shout it out to the night. Give me what I deserve cause it’s my right.”

35. Somewhere in My Broken Heart (Billy Dean)

A man is left heartbroken after his lover ends the relationship and now he must come to terms with how to move on and forgive. 

“You made up your mind it was over after we had come so far. But I think there’s enough pieces of forgiveness somewhere in broken heart.”

36. Ships That Don’t Come (Joe Diffie)

This song revolves around the existential conversation and shared experiences between two men at a bar. 

“He said it’s only life’s illusions that bring us to this bar. To pick up these old crutches and compare each other’s scars.” 

37. The Tips of My Fingers (Steve Wariner)

Wariner sings about the heartbreak a man feels after his lover finds another man and leaves him behind with the love he still has for her. 

“Somebody took you when I wasn’t looking. I should have known from the start, it’s a long, long way from the tips of my fingers to the love hidden deep in your heart.”

38. For My Broken Heart (Reba McEntire)

This song illustrates the end of a relationship and the disillusionment of the woman who thought the world would stop for her broken heart. 

“Last night I prayed the Lord my soul to keep. Then I cried myself to sleep, so sure life wouldn’t go on without you.”

39. What Do I Do With Me (Tanya Tucker)

A woman is at a crossroads, not knowing where to go or what to do after her lover has left her life. 

“Since the day that you left I’ve been asking myself, is this how it’s gonna be? Without you, what do I do with me?

40. I Miss You a Little (John Michael Montgomery)

Although the narrator doesn’t want to admit it, he is lost without his lover and misses the little things about their relationship. 

“When I go by our old house I pretend that you’re still there, waitin’ for me on the porch but there’s just an empty chair.”

41. How a Cowgirl Says Goodbye (Tracy Lawrence)

In this song, the male protagonist has been cruelly left by his girlfriend who became quickly disinterested in him. 

“That’s how my whole world slowly came apart. With a cold and empty stare as if I wasn’t there. She didn’t even stop to cry. That’s how a cowgirl says goodbye.

42. Missing You (Steve Wariner)

This song is about a man who is missing his lover after their relationship ends. He is static in the heartache he feels. 

“Why did you have to go? Why am I missing you so? One heartbeat at a time I’m going out of my mind, missing you, missing you.”

43. Cold Day in July (The Chicks)

A woman recounts what happened and what it felt like the day her lover moved out and they went their separate ways. 

“You said that we were gonna last forever. You said our love would never die. Looks like spring and feels like sunny weather but it’s a cold day in July.”

44. Carry On (Tim McGraw)

The man in this song acknowledges the advice of his late mother who he believes is always with him and his family through the good and bad times. 

“Mama went to sleep one night and never woke up. Daddy cried a tear into her old coffee cup. Now all he wants to do is drink the hurt all away.”

45. Billy Austin (Steve Earle & the Dukes)

Earle gives rise to the voice of those that are wrongly accused, death-row prisoners in this powerful song. 

“Don’t remember Oklahoma, been so long since I left home. Seems like I’ve always been in prison, like I’ve always been alone. 

46. The Thunder Rolls (Garth Brooks)

This third person narration conveys the abrupt moment that a woman discovers her husband has been having an affair. 

“The thunder rolls and the lightnin’ strikes, another love grows cold on a sleepless night as the storm blows on. Out of control, deep in her heart, the thunder rolls.”

47. I Cross my Heart (George Strait)

In this beautiful love song, the protagonist promises to be all that his lover deserves and to give her everything she needs. 

“You will always be the miracle that makes my life complete. And as long as there’s a breath in me, I’ll make yours just as sweet.”

48. Strawberry Wine (Deana Carter)

A woman equates her first love to summertime and the taste of strawberry wine, recognizing that he might have been the one that got away. 

“We drifted away like the leaves in the fall. But year after year I come back to this place just to remember the taste of strawberry wine and seventeen.”

49. Meet in the Middle (Diamond Rio)

This song describes a love story by the couple’s ability to make compromises and see eye-to-eye amidst disagreements. 

“We’d gain a lot of ground cause we’d both give a little. And there ain’t no road too long when you meet in the middle.”

50. Every Light in the House (Trace Adkins)

After the split from his wife, the narrator promises to leave a light on in case she ever decides to return. 

“The backyard’s bright as the crack of dawn. The front walk looks like runway light. It’s kinda like noon in the dead of night. Every light in the house is on just in case you ever get tired of being gone.”

RELATED: 100 Sad Songs (With The Saddest Lyrics) That Will Make You Cry​

Isabella Pacinelli is a writer who covers relationship, self-love, spirituality, and entertainment topics.