My brother-in-law used to have a boss named Richard Hare. And yes, he went by his nickname, "Dick". (They stopped traffic in a busy airport once when Mr. Hare was paged to the courtesy phone. )
I worked at an answering service for 6 1/2 years, and oh, boy, did we get some lulus!
One of the worst I read out to one of our clients, just after I got out of training was
J. Blankenshit
Needless to say, I lost it. Fortunately, the client found it a hilarious faux pas, and said he'd have to tell the caller, who was a friend. It turns out the operator who took the call misspelled it, and the name was actually Blankenship.
Another good one I had to read out [fortunately when I was more seasoned, and better able to control myself] was Manuel Concepcion. That led to a LOT of giggles in operations.
Whenever we got calls from nice young Hispanic men whose name was pronounced, "Hey soose," it inspired some religious fervor, considering the spelling, Jesus. There was more than one outcry of, "Hey everybody, I just got a call from Jesus!" pronounced properly as the Christian Messiah "G Zuss".
Others I heard, that I fortunately did not have to read out were:
This actually happened back in Mississippi and made the news! There was a guy living in Jackson with the last name of Shihead (I forget what his first name was), but the phone directory had misspelled his name as "Shithead", and pretty soon he was getting crank calls from people saying to him, "Hey Shithead!"
Not on the topic of outrageous names, but our last name is pronounced /bloom/. In high school (years ago), my bro and his English Teacher came up with the name Roses May, possibly for his daughter one day down the road.