Basically he picks a bunch of ideas or voices, arbitrarily decides they had utmost influence on history, giving no evidence for this, then connects them to cherry-picked historical events, omitting any events that would contradict the narrative he wants to present, and also any counterpoints within the ideologies he's 'debunking.' If anyone seriously finishes watching those shows and takes it all at face value, they have some serious epistemological issues.
Was Rand happy? Think how ridiculous this is: all the stuff she accomplished in her life time, and the documentary focuses on one spell of unhappiness stemming from a personal betrayal, to paint her as a 'failed invidividual.' Think of all the difficulties other philosophers/writers ran into - yet we let their ideas stand on their own merit. Of course Rand was not happy every single day, and there's nothing about her philosophy that suggests she ought to have been, but she was (rightly) satisfied with her life.