Just finished watching it so you're getting quick responses which is maybe doing the film a disservice as I think there are multiple things going on. Ironically considering the content of the movie I couldn't find it in an UK streaming service and you couldn't even buy it on YouTube. For full irony it should have only been available on BET but the world isn't that funny.
1) I'm missing some jazz subtext I think. I'm assuming Issa Rae's character is a play on Sinatra and maybe there is some connection between him and Monk that may play into the story
2) I enjoyed how it explored and subverted stereotypes whilst also reinforcing some . There are layers here. For example Monk wants to live in a world where his race doesn't define him yet the film shows him suffering from several micro aggressions particular at the beginning. There is a promiscuous drug taking black man but he's gay. There is a black maid but she's also kind of family but then she rejects the apron that Monks dad picked out for her. There are no dad's in any of the families but it's Cliffs kids that have rejected him.
3) Sometimes the points are subtle but sometimes they are obvious. The film is making fun of virtue signalling white people and their attempts to champion real black voices (despite ignoring the black voices) but the depictions are so on the nose that I really wonder if it's also making fun of white people like me who consider themselves above that. Is the final shot with Lakieth Stansfield making fun of me for also not really being sure if it is Lakieth Stansfield?
4) I wonder how much of Monks character is informed and inspired by someone like Harry Pace.
5) I'd really like to hear a writer and directors commentary to explore some of these layers as it's taking shots at lots of people I think including people like Monk. He hasn't read Sintara's book but assumed it's all a fiction like his yet she talks about her research which gives it some reality that Monk hasn't considered. He's pompous and elitist which are stereotypically white attitudes.
6) I was reminded of how I felt when I watched the Luke Cage series. I felt a little like I was watching people performing blackness for a white audience. I reached out to a woman I kind of knew who lived in New York to ask how exaggerated it was but she told me it wasn't that outlandish. There is still a discomfort I have watching that which I think was explored a little in the discussion between Monk and Sintara and their books.
7) In some ways it's a stereotypical white story about a middle class family which would affirm Monks desire to live in a race blind society BUT blackness is still central to it. The film may be making fun of me writing that sentence as a white guy trying to appear educated. Layers :)
8) with some of these big themes being explored I did enjoy some of the smaller moments. Cliff dancing with his mum but then leaving in the morning with "this family will break your heart" was quite moving and the little bits revealed about Monks dad I think are quite important. He's a black dad that's not around but still very present.
9) the three endings were quite savage in different ways and I think central to how the film should be understood but I'd need to watch it again and see how they impact the movie. I think it's possibly saying race is simultaneously important and unimportant but not in the ways we imagine.
If I could give this 9 likes, I would! Very good take. Funnily enough, I was immersed in the world cos I've seen the tropes depicted all my life, and yet I identified more with 'Thelonious' more than anyone.
*1) Good pick up on the 'jazz' element where both exist in the same world, but one much more sophisticated than the celebrated simplicity of the other; a great micro allegory for the film and really easy to miss.
*2) My take on this is that I was immediately struck by the chaotic nature of the household, again as you say 'full of stereotype'; success and failure and the inclusion of a maid usually reserved for well off families and yet they are middle class with a maid. I couldn't help thinking of
"Gone With the Wind" at this point, perhaps unfairly because I know she's treated as family and it's a source of employment.
*3) To me echoes the attempt at tanking the book with outlandish suggestions with the tropes of Rap; the more vulgar the action in the songs or by the 'artists', the more popular they become with White society.
*5) I think even if 'Monk' hasn't read the book, he reacting on what he hears in the reading from a clearly educated woman and it jars with him why she would debase herself.
*8) I agree about the moment between 'Cliff' and mum's moment of unity only for her to break that moment. It caught me off guard. I didn't really focus on the fatherhood aspect, quite honestly, as I was busy analysing everything else! But, I will come back and watch it again tonight (something I rarely do with films).
And I don't think it's Lakeith Stansfield at the end (although it IS something he would do!).
Yes, I enjoyed that read and concur with much of what you wrote!