"Holes in the Floor of Heaven" is a song co-written and recorded by American country music artist Steve Wariner. It was released in April 1998 as the lead-off single from his album Burnin' the Roadhouse Down, and was his first solo single in three years. It peaked at number 2 in both the United States and Canada. The song, written by Wariner with Billy Kirsch, won the award for Song of the Year in 1998 from both the Country Music Association (CMA) and the Academy of Country Music (ACM).