The last thing you'd ever want, used as a simile.
"If the zoning board rejects our proposal, we'll be forced to allow the superhighway to divide the property, and then 9 holes might be on one side, and the other 9 holes on the other side. We need that like we need a Hole in the Head."
by skydog70 May 07, 2007
1 more definition
A sunroof in a vehicle
I just bought me a new Cadillac with a Hole In The Head
by Cuch80 November 05, 2005