Went to high school with a guy in which his last name was ****. His father went by the name Clifford but that was actually his middle name. His fathers real name was Harry......... I would have gone by Clifford also. His father was pretty old, but even back in the 1940's when he was born you would think that even then they would have thought twice about the issues with naming him Harry.
Also can remember back in junior high when I had to get my physical for sports, the Doctor's last name was Pollpeter. That was a bit awkward when he asked me to drop my pants for the "old turn and cough" part of the physical, my response was "Yes Dr. Pollpeter"
On the reverse though the most kick *** name I have ever heard is the name of my wife's Uncle. He is Fillipino and his name is Perfecto Supremo. I kept imagining him wearing an Evil Knievil jump suit with the stars blazing and the cape flowing.