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Excellent advice, thanks! A minor note: The missile crisis was in October 1962 (relevant for X-Men: First Class timeline), so 6 years before
the release of Memories of Underdevelopment? It took really long to make.. ?
Your description of I am Cuba makes the name Leni Riefenstahl spring to mind ;-) I.e. great directors of propaganda films. Western nations have had lots of propaganda movies as well, but the directors were less accomplished, maybe? But I digress.
I go to film festivals sometimes, where one can see Cuban films, Only Cuban filmmakers (Ry Cooder and Oliver Stone being the notable exceptions) are allowed to film in Cuba, so all Hollywood movies, European movies etc (if there are any) that are set in Cuba, are filmed elsewhere (often in the Dominican Republic, i.e. on the island of Hispaniola - or in Puerto Rico; in both instances fuelling local economies). Propaganda-tinged movies are still being made in Cuba, although the state also sponsors filmmakers that quite clearly question the Cuban system.
Anyhow, the querie here is about films dealing with the days of the revolution, up until the 1959 takeover in Havana. Your recommendations seem excellent, though, and I had heard of neither, so thanks again 
it's not a revolution, it is marxism=failure, everyone is starving Jun 22, 20:19
Wasn't asking for political opinions at all, dude. {nm} Jun 22, 20:42
(btw, you are way misguided - more on the IM)) Jun 22, 20:55
for your viewing pleasure....(not exactly what you were looking for, but still a good list) Jun 22, 21:01
Impressive list, thanks. It's got "The Good Shepherd", "Che" and "Thirteen Days", but is missing lots of others. Jun 22, 21:11
Dirty Dancing: Havana Nights? {nm} Jun 22, 20:23
I believe my sister and mother enjoyed that one together... They are both completely uninterested in history, geopolitics etc. Jun 22, 20:45
I Am Cuba [1964] & Memories of Underdevelopment [1968] Jun 22, 22:47
Excellent advice, thanks! A minor note: The missile crisis was in October 1962 (relevant for X-Men: First Class timeline), so 6 years before Jun 22, 23:39
Great choices ! -- I would also suggest watching Wim Wenders' documentary Buena Vista Social Club (1999)... Jun 23, 07:14