I was working on an ad for an area hospital using a photo that depicts a married couple with a child sitting on a porch. In the photo, the husband was white, the wife was Asian.

Client: The ad design looks great! But we're not sure about the photo you chose.

Me: If you want, I can search for a different photo, or if you have a different photo in mind, I can replace it with that one.

Client: It's just that the wife doesn't match our target demographic. Could you maybe find a different face and Photoshop it over hers?

Me: ...I'm sorry could I what now?

Client: Could you find a different face and replace hers with it? Maybe someone more in our demographic? We don't want to lose such a perfect photo.

I'm sorry to admit that I proceeded to make up a bunch of reasons why it would be much more affordable for them to just pick a different photo, INSTEAD of calling them out for being grossly racist, which is what I wanted to do.

I maintain a professional presence on social media and most of my clients are Facebook friends.  Towards the end of a status meeting one day:

Client: I notice that you have many friends of color on Facebook.

They then started complaining about their blue-collar workers, most of whom are racialized.

His complaints made this clear.

I was asked to illustrate an ad for a client.

Client:  Let’s make the child ambiguously racial. We want this to have a wide appeal.

I gave the drawing of the kid a middle tone complexion.

Client: Hm, can we lighter on the skin?

I changed the skin color to a tanned complexion.

Client: Can we go lighter?

I made the illustration fully Caucasian with blond hair and blue eyes.

Client: Perfect!

I design monuments and other wayfinding systems. Recently I had a request to design a monument for an apartment complex in another state, so I researched the types of monument being used in the area and submitted a design of a double faced ground sign with a masonry base.

Client: Can you raise the monument off the ground about 7 feet?

Me: You want a super tall base under the sign face?

Client: No. I want it on posts or something. I need to see under and through it.

Me: Ummm.. Okay. Why do you need to see under it?

Client: The blacks around here are always hiding behind things. So I want to make sure they can’t hide behind the sign.

Whoa.

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.