Songfacts®:

• "Holes In The Floor Of Heaven" might be seen as a latter day Country & Western version of "My Yiddishe Momme," but unlike the Jack Yellen inspired tribute to a departed mother, this is a good song in its own right; although it might be described as a bit syrupy, neither the words nor the melody is inferior.
  
  The title is the giveaway, what falls through holes in the floor of Heaven? Tears, of course, that's what the rain is. The song starts with the death of the narrator's grandmother but progresses to the premature death of his wife, but she can be anyone you want her - or him - to be - not necessarily a wife or lover, but a parent, sibling, child, or just a friend. In a 1999 interview with Jim Bessman of Billboard magazine, Steve Wariner echoed these sentiments, the song, he said, struck a chord with many people who related it to their own personal family losses.
  Unsurprisingly, it also struck a chord with the C&W establishment winning both Single Of The Year and Song Of The Year at the 1998 Country Music Association Awards.
  
  Wariner co-wrote the song with Billy Kirsch. >>

  Suggestion credit:
  Alexander Baron - London, England