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.