Books
Serious Books - Focused on trading psychology, trading philosophies, risks, and other "environments".
"Extraordinary Popular Delusions & the Madness of Crowds" by Charles Mackay
"Against the Gods" by Peter L. Bernstein
"Mobs, Messiahs, and Markets" by William Bonner and Lila Rajiva
"Enhancing Trader Performance" and other books by Brett Steenbarger
"Behavioral Finance and Wealth Management" by Michael M. Pompian
"The Black Swan" and "Fooled by Randomness" by Nassim N. Taleb
"Trading in the Zone" by Mark Douglas
"Market Wizards" by Jack Schwager
"Emotional Intelligence 2.0" by Travis Bradberry & Jean Greaves
Entertainment Books - a few miscellaneous books any speculator might enjoy.
"The Coffee Trader" and other books by David Liss
"The House of Morgan" by Ron Chernow
"Sway" by Ori Brafman and Rom Brafman
"Confidence Games" by Mark C. Taylor
"Behavioral Game Theory" by Colin Camerer (for late night reading of course)
"The Education of a Speculator" by Victor Niederhoffer