Steve Wariner’s “Holes in the Floor of Heaven” is widely considered to be one of the saddest country hits of all time.

The song was released in 1998 as the lead-off single from his album Burnin’ the Roadhouse Down and became Wariner’s first solo single in three years. It peaked at No. 2 in both the United States and Canada. And by the end of the year, the song won big both on Country Music Association and the Academy of Country Music, bringing home the award for Song of the Year.

Watch Richard Goodall’s cover version below.

One Of The Saddest Songs You’ll Ever Hear

Written by Steve Wariner with songwriter Billy Kirsch, “Holes in the Floor of Heaven” tells the tale of a man’s sadness upon the passing of his grandmother when he was just “one day shy of eight years old” and then his young wife who he thought he’d grow old with.

When he was just a child, during one cold lonesome rain, her mother thought him something he had never forgotten.

“My mom smiled, said: ‘Don’t be sad, child. Grandma’s watching you today. 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. An’ sometimes if you’re lonely, just remember she can see. There’s holes in the floor of Heaven, and she’s watching over you and me,” the song goes. The man in the song held on to this hope, especially when he was missing his wife.

In one interview, Wariner said that “Holes in the Floor of Heaven” is the biggest accomplishment of his career. It was actually inspired by a phrase Billy Kirsch’s wife heard a couple of years prior, and that was “holes in the floor of heaven.”