Many people agree that “Holes in the Floor of Heaven” by Steve Wariner is among the most depressing country songs ever.

As the first single off his album Burnin’ the Roadhouse Down, the song was released in 1998 and marked Wariner’s return to the solo music scene after a three-year hiatus. In the US and Canada, it peaked at number two. And by year’s end, the song had won big at the Academy of Country Music and the Country Music Association, taking home Song of the Year.

Watch Richard Goodall’s cover version below.

One Of The Saddest Songs You’ll Ever Hear

“Holes in the Floor of Heaven,” which was co-written by Steve Wariner and lyricist Billy Kirsch, is about a man’s sorrow at the deaths of his grandmother, who died when he was only “one day shy of eight years old,” and his young wife, who he had hoped to spend his retirement with.

Her mother told him something when he was a little child, during a chilly, lonely rainstorm. He never forgot it.

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“Don’t be sad, child,” my mother remarked with a smile. Grandma is currently observing you. Because of the holes in Heaven’s floor, her tears are streaming down. You can tell she’s watching and wanting she could be here right now because of this. And sometimes, keep in mind that she can see you if you’re lonely. The song goes, “There are holes in the floor of Heaven, and she’s watching over you and me.” Particularly while he was missing his wife, the man in the song clung to this optimism.

According to Wariner, “Holes in the Floor of Heaven” is his greatest professional achievement, as stated in an interview. Actually, it was inspired by a comment Billy Kirsch’s wife had heard a few years earlier about “holes in the floor of heaven.”

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