I have often found myself referring people to some specific books, articles, blogs, and TV series. Here's a list of some recommendations:
Marc Shapiro's The Limits of Orthodox Theology: Maimonides' Thirteen Principles Reappraised -- Some of the most fascinating thoughts penned by rishonim and acharonim which today are considered by many not ever to have been acceptable within Jewish theology.
Haym Soloveitchik's "Rupture and Reconstruction: The Transformation of Contemporary Orthodoxy" -- Basic treatment of the loss of the mimetic tradition within Orthodoxy. Menachem Friedman has a lot of stuff on Orthodoxy's becoming a "society of scholars" as well, but this is the basic treatment I recommend for people who aren't immersed in the academy.
Matt Taibbi's The Great Derangement -- Matt Taibbi posits that people who can't have faith in their media or cynically manipulative congresspeople turn to woo-woo groups such as the 9/11 truthers and evangelical fundamentalists. He gives us a gadfly's look at all of these groups, using his press pass as a Rolling Stone journalist to go to Congress and going undercover to infiltrate woo-woo land. Even if you disagree with his thesis, his journey through these odd corners of American society (and particularly his take on certain congresspeople) proves fascinating.
Sam Harris's The End of Faith: Religion, Terror, and the Future of Reason -- Sam Harris is my favorite of the New Atheists (no, that doesn't mean I agree with him on everything) and I've read all his books. Herein, he takes issue with faith, fundies, and those who don't understand that beliefs have consequences. But he also shows that a person can have spirituality without having to have blind faith in holy books.
Christine Garwood's Flat Earth: The History of an Infamous Idea -- I read this book and thought, "meh, that was okay, nothing special." Then I began to notice how people I used to argue with were using arguments which were the exact same as the arguments propounded by flat-earthers. Only after reading this book did I realize that it was one of the best books I've ever read; it has helped me tremendously in understanding Biblically based woo-woo like young earth creationism and anti-evolutionism.
Louis Bernstein's Challenge and Mission: The Emergence of the English Speaking Orthodox Rabbinate -- Awesome treatment of the history of much of American Orthodoxy (mostly focused on the RCA's development).
Dovid Holzer's The Rav Thinking Aloud: Transcripts of Personal Conversations with Rabbi Joseph B. Soloveitchik -- A Rosh Yeshiva who maintains that only he and one other individual are true talmidim of the Rav once told me that Kierkegaard was not a major influence on the Rav ("Kant, yes...Kierkegaard, no, no."). This book gives the lie to that and many other errors, such as the assertion by Nisson Wolpin and Dovid Hollander that the Rav was against involvement in the Synagogue Council of America. The Rav's discussion on Zionism is much more pragmatic here than in his other treatments of the issue.
The Rav's Kol Dodi Dofek -- A more passionate case for Zionism.
The Rav Speaks -- Another very passionate case for Zionism.
Community, Covenant, and Commitment -- Interesting letters from the Rav to others.
DES's Torah, Science, Et Al. blogsite -- List of great rabbis (past and present) who think some of Chazal's words were written not based on superior Divinely given knowledge, but based on incorrect information regarding the natural world.
Paranoia Agent -- Most underrated anime ever. Who is this Boy with the Golden Bat wandering around Japan knocking people unconscious and causing them to lose their memories? Aesthetically explores humanity's existential crisis. (Warning: not tznius -- nu, it's anime -- violence, cursing.)
Fullmetal Alchemist Brotherhood -- Hard to describe. (Better subbed than dubbed. Warning: not tznius -- nu, it's anime -- violence, cursing.)