Thanks for Stephen Faassen for asking the question: Why can’t we be funny?
Art & Copy, a documentary on the modern history of advertising and marketing. George Lois is my spirit animal.
Art of Action by Stephen Bungay. Probably the most under-valued book on strategy in business.
Tools of Titans by Tim Ferriss. A collection of everything interesting form his more than 200 podcasts of very interesting and successful people.