OCR provides interpretive works, while giving full credit to the original composers and game creators, distributed for free. So, in fact, it is free advertising and creative arrangements available for no cost to anyone anywhere except the bandwidth, which we pay for via donations. Despite Fair Use's ambiguity, it needs to be as such because there could be billions of cases that are different and not one universal Fair Use clause could cover them. Fifty couldn't. A thousand couldn't.
Case in point: the photographer was most likely in his right to sue for use. It sucks, and the guy is definitely a dick who lives in a 72-room mansion, but it was in his legal right most-likely. He'd need a very solid case for not licensing the art if he licensed all the music. If he inquired and the guy said he wouldn't license, it was really stupid to go ahead and do it anyway. It is possible that it just slipped his mind, but this is what happens when you don't cover every angle airtight. He was just unlucky enough to get a huge douchebag who owned the rights.
The same way the Westboro Baptist Church shows the worst side of Free Speech, so to does this show the worst abuse of defending copyright against allegations of Fair Use, and without the satisfaction of a trial. Sucks, and yes as I've said, Maisel is a total asshat, but yeah.