Okay - many years (eons) ago, I worked in another state for an attorney who was blunt. We had new clients who raised smelly farm animals and whose last name was Horr. So - As I'm about to bring a new client into his office, he shouts out, "What time's the stinking Horr's supposed to be here." I shuffled around for a minute (mind you, I'm 18 at the time; and finally turned to the new client and said, "It's the punch line from a joke he couldn't remember earlier."

#2
I'm a grant writer. My first multi-million dollar grant application, which was the 3rd highest rated in the country, and which was chosen as a sample by the federal government, and which had been proofread at least 15 times by 8 different people, contained the phrase:
"...a nutritious snatch will be served to the afterschool students."

We didn't discover the error until AFTER all of the above, and we had to call the top lady and ask her to please correct the phrase.

I don't think I'll ever forget those two incidents, and #2 is why I always say NEVER rely on spell-check!