Dr Strangelove was probably the most overtly insulting to the establishment movie ever made. Mocking real people, real corporations, real “secret” government programs, and putting on display the hubris of the American Military Industrial Complex.
The most covertly insulting film was Kubrick’s next film, 2001. As an example, IBM was so pissed off when they saw the movie, they demanded all their logos be removed from the film.
Watch 2001 from the lens of someone being paid to make a film to glorify a technocrat, AI controlled future, who secretly made a film which exposes the dangers of it.