"Diggin' a Hole" is a song by Canadian rock band Big Sugar. It was released as the lead single from the band's 1996 album, Hemi-Vision. The song was co-written by Canadian musician Andy Curran and well known Canadian actor and TV host Dan Gallagher. The song was successful in Canada, reaching No. 9 on the RPM Hit Tracks chart. The song was re-released in 1999 on the U.S. version of Big Sugar's next album, Heated. Between 1995 and 2016, "Diggin' a Hole" was the fifth-most-played song by a Canadian artist on rock radio stations in Canada.