10 Sad Country Songs Of The 90’s

Dust off your boots and grab a hanky as we go over 10 sad country songs of the '90s. Country music is known for producing some of the saddest songs in history and the '90s was no exception for this. These songs cover a wide range of topics from broken hearts to the death of a loved one.

  1. “Holes in the Floor of Heaven” by Steve Wariner (1998) In the song the listener hears of three different events in a young man’s life including the lost of his grandmother, the lost of his wife and then when his daughter gets married he is struck with sadness at missing his wife. During each event it rains and the singer explains the raindrops are the tears from his loved ones in Heaven.
  2. Go Rest High on that Mountain” by Vince Gill (1994) The song also included Patty Loveless and Ricky Skaggs. This is a tribute to Gill’s brother who passed away.
  3. “Love, Me” by Collin Raye (1992) This song is about an elderly couple and the man is telling his grandson their love story. The story tells how the boy’s grandmother’s father didn’t want her to marry his grandfather. It’s a beautiful song about not giving up on the ones that you love because they will always be there even in death.
  4.  “Wish I didn’t Know Now” by Toby Keith (1994) This song is about a man who found out that his girlfriend cheated on him. Later he wishes he hadn’t known because he was happier even if he was living a lie.
  5. Someone Else’s Star” by Bryan White (1995) The singer in this song is alone and wishes he could find the love of his life. The man feels like he is wishing on “someone else’s star” because good things seem to only happen to others.
  6. “For my Broken Heart” by Reba McEntire (1991) This is a breakup song about how a woman isn’t sure she can make it through the pain. After crying herself to sleep she finds that the world went on and didn’t stop “for my broken heart”.
  7. “How Can I Help You Say Goodbye” by Patty Loveless (1994) This is a beautiful song about a mother who has helped her daughter through the tough times in life and then end tries to help her say goodbye. This song will make you want to call your mom right away.
  8.  “Somewhere in my Broken Heart” by Billy Dean (1991) This sad country song is about letting go of love. In the song a man tells a woman to go ahead and leave him. In the song he says he wishes “somewhere in my broken heart” he can find a way to live without her.
  9. “Neon Moon” by Brooks & Dunn (1992) This is the song about being lonely and the end of a relationship. It tells the story of man that feels so alone that he spends “most every night beneath the light of a neon moon.”
  10. “Wish you were Here” by Mark Wills (1998) This is a song of lost and love that can even conquer death. A man dies in a plane crash and then later his wife supernaturally gets a postcard in his handwriting from Heaven that starts out “Wish you were here…”
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