I have an amateur interest in the history and social context of TCS, Math, and Science more generally. I list here some documents (long books, short articles, MO questions...) with a historical (and often personal, which I like) tone that I found especially interesting, in no particular order.

• Golden Years of Moscow Mathematics

• Sharon Traweek's "Beamtimes and Lifetimes"

• Babai's "Email and the unexpected power of interaction"

• Andrei Sakharov's memoirs

• Richard Rhodes' "The Making of the Atomic Bomb"

• Widely accepted mathematical results that were later shown to be wrong?

• What are some famous rejections of correct mathematics?

• In "splendid isolation"

• The half-life of a theorem, or Arnold's principle at work

• Emanuele Viola's "Myth creation" blog posts

• How Are the Mighty Fallen: Rejected Classic Articles by Leading Economists 

• Laurent Schwartz's "A Mathematician Grappling with His Century"

• Norbert Wiener's "I Am a Mathematician"

• Paul Halmos' "I Want to be a Mathematician"

• "Discrete Thoughts" by Mark Kac, Gian-Carlo Rota, and Jacob Schwartz

• Gian-Carlo Rota's "Indiscrete Thoughts"

• Paul Hoffman's "The Man Who Loved Only Numbers". This book got me hooked on discrete math as a high school student.

• André Weil's "The Apprenticeship of a Mathematician"

• Stanislaw Ulam's "Adventures of a Mathematician"

• Mark Kac's "Enigmas of Chance"

• Goro Shimura's "The Map of My Life"

• Neal Koblitz's "Random Curves"

• Mauldin's "The Scottish Book"