Movies are not realistic about working world. Either the dipiction is too glamorous or too grim. Neither books nor movies tell you how mind numbing and boring it really is.
"The Prince" by Macchiavello
Documentary
Difficult question - books are my "refuge" from reality - the movies or books are not so much relatable to me (I read a lot but not because I am looking for reality)
The Seven Samurai tells you everything you need to know about working with other people, and especially project management. Miller's Crossing is a great movie about ethics, and especially clean up an interpersonal mess.
Office space
Gary vaynerchuck. Read his books and follow him on social media. He will change your life.
The beginning part of Joe vs the Volcano and the remake of the Secret Life of Walter Mitty.
Apollo 13, Decisions 2.0
Wolf of Wall Street
Patrick Lencioni's books are excellent.
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