Somehow I'm guessing your friend would be the target of the easily butthurt cancel culture today... regardless of his intentions. That first piece reminds me of R. Crumb's infamous Angelfood McSpade.
Very frequently, it's not the black folks who are offended, but virtue-signaling white liberals.
Around here we have a bloke called Anton Kannemeyer, who has become notorious for his merciless satire, supposedly offensive to blacks. And perhaps it is too, to some, but they miss the point: what he is satirizing is, for the most part,
white perceptions, guilt, political correctness etc. His pictures are not so much about black folks as about how they are seen by whites, specifically a particular brand of white pseudo-liberal. We have/had many of those around here: they waved placards against apartheid, but knew no black people personally (apart from the black servant and gardener - "but we treat them well"). They angrily demanded that apartheid end, but the moment it did, they started emigrating in droves.
Ultimately,
they are the people who see black folks the way Kannemeyer depicts them - as blackface abstractions and caricatures.
And the white liberals' worst nightmare:
He's not too amused with cancel culture:
WARNING: Some readers may find the images in this article offensive. Anton Kannemeyer's flirtations with controversy and racially-charged content have been a huge part of success. But with the appetite for his work diminishing, he finds himself on the receiving end of criticism. Arts24 caught...
www.news24.com
I was asked in one of the independent drawing/painting classes I was taking to maintain my license, why none of the women... or men... in my paintings were African-American. I told her that I felt the issue was loaded. There are those who would take offense at a white artist painting an African-American... especially if she were nude or nearly-nude. On the other hand, is avoidance of African-American models a form of racism? Hell, just painting women as a male artist is enough to offend some. With time, however, I came to realize that the only thing an artist can do is be honest to him or herself and paint what and how one wants without worrying what others might think.
Yup, you can't win on that point. Paint black folks, and you are guilty of cultural appropriation. Don't paint them, and you are guilty of ignoring or marginalizing them. Paint images of apartheid police laying into black protestors with whips, and you are guilty of commenting on stuff you can't possibly really understand. Paint bland flower still life instead, and you are guilty of ignoring the world's issues and merely catering to bourgeois taste.
It's not about what you paint. It's about who you are, and being a white man renders you guilty and tainted with original sin, automatically, irrespective of what you do or say. It is precisely for that reason that apologizing to these folks is the very worst thing you can do, because they have never once, that I am aware of, graciously accepted a heartfelt apology. On the contrary, in their eyes it simply confirms your guilt, and the moment you apologize the attacks intensify. They are after all not out to merely punish you a bit. They aim to cancel you, destroy your entire life and career, unmake you.
Why? Just possibly because in your work, or whatever it was you said or tweeted, they see themselves reflected.