I could watch "Apocalypse Now" over and over. I'm fascinated by the Vietnam War and all of its complexities - the politics, the people, the madness, the music, the drugs, the protests, the divisiveness, the ignorance, the battles, and the inevitable outcome. If you haven't seen it, the movie is a brilliant story with magnificent acting and cinematography.
As for books, I could read "Into Thin Air" by Jon Krakauer over and over. I think it took me two days to finish.