Holy Innocents' Cemetery - A medieval cemetery so overfilled, buildings were constructed around it, which were then filled with exhumed bones up to the rafters to make room for more bodies. ( en.wikipedia.org )
Heartbeat in the Brain - Lost 1970 documentary in which the director/subject drills a hole in her forehead with a dentist's drill ( en.wikipedia.org )
John Murray Spear - Minister who attempted to create an electrically-powered metallic machine god which was dubbed "The New Motive Power" ( en.wikipedia.org )
A Hole in My Heart - 2004 film notable for its explicit imagery, including close-ups of vaginal reconstruction surgery and a masturbation scene with a toothbrush ( en.wikipedia.org )
Trepanning - a surgical intervention in which a hole is drilled into the human skull. Evidence has been found in prehistoric human remains from Neolithic times onward ( en.wikipedia.org )