ohhhh yeah plenty of times, here is a funny story from high school:
Was walking down the hall with my friend john (me being a white guy and him a black guy) to class because we had a pass to go talk to a teacher then come back, and there were a few black girls at their locker a bit down the hall by the classroom that John and I were heading towards.
we were talking casually and all of the sudden he decides to yell out "WHUIITEEE POWERRRRR!" and proceeds to look at me really fast in utter shock that I would say such a thing, and in that moment all the black girls turn and look at me with the most pissed off face you can imagine.
of course, I was caught completely off guard and my brain just goes into "oh fuck" meltdown mode..
cutting out all the bullshit, i get sent to the principal's office, get a 10 minute stern talk about racism and how wrong it is to ever proclaim to have pride above another, and then i get sent back to class...all the while, my friend john is cracking up in the hallway as he was trying to get into the office to explain it was all a blown out of proportion joke.
eventually, the principal looked at us both in disgust and sent us about our way, but she was still super pissed off regardless.
I laugh at the story all the time, and my friend John still pulls stuff like that in public for shits and giggles, but it definitely sucked at the time and the principal never quite looked at me the same after that.
also obviously said a few really *bad* racial jokes here and there, that whole "taking it a bit too far" moments. (Don't worry, i'm an equal opportunist bigot, I make fun of white people the most, can't tell you how often I make fun of myself.)