I was designing a site for a website dealing with school-age kids.

The original placeholder image we used had a gaggle of kids: about 20 Caucasian girls, one Caucasian boy, and two East Asian girls.

Client: That's not diverse enough.

Me: I agree. Let me see what else I can bring up. 

I found three images that might fit our needs, which the client kindly rated by "diversity."

The first was a handful of African-American, Caucasian, and East Asian kids, split roughly evenly between boys and girls: 

Client: Maybe diverse enough.

The next had four African-American boys, one Caucasian boy, and one African-American girl: 

Client: That's more diverse.

The last had three African-American boys: 

Client: That's the most diverse.

You keep using that word. I do not think you know what it means.

Not one of their images had any Middle Eastern or Latin kids.

I was hired to illustrate a cartoon design for a tee shirt. It was supposed to be 2 large "ants" having a picnic, with tiny cartoon people running around the picnic basket and blanket.

Simple enough. Two colors, red and black on a grey tee. I did most of the cartoon lines in black, and used red as a fill color on the checkerboard blanket and the two ants who were having the picnic.

When I showed the client, they didn't like it.

Client: It looks racist to me. Those ants are stereotypes of African Americans.

I wasn't sure why or how. They were red cartoon ants after all. 

Me: Oh, I'm sorry. I don't really see it but I can change them if you don't' like them. 

The changes she wanted me to add? Large cartoon lips and a big hair bow to the girl ant, and a gold chain and baseball hat to the boy ant in solid black ink. 

For added WTF, the client was an African American woman. I'm still scratching my head on this one. 

Early in my career (circa 2008), I was hired by a major retailer to work in their internal human resource department. I joined the company at the same time as several other new hires working across the chain. We were greeted by someone whose title was “Chief Intern.”

Client: The best way to get along is if you treat this like 8 Mile. I am Eminem and you are all my n****rs!

I quit after two days... and I wasn't the first.