8 Books That Will Help You Get Your Head Around the Modern Political Landscape

Old School: Life in the Sane Lane, by Bill O’Reilly and Bruce Feirstein
Anyone who thought O’Reilly, famed anchor of The O’Reilly Factor, had gone softly into writing best-selling history books, will find the old O’Reilly back to his fiery ways in this latest blast from the FOX News pundit. O’Reilly examines our changing times with his usual acerbic wit, analyzing the rift between those he classes as “Old School”—people who see life as being filled with challenges, and defined by how we meet those challenges—and “snowflakes,” the often younger crowd who prioritize access to safe spaces, fighting against marginalization, and other social justice issues. O’Reilly (with James Bond screenwriter Feirstein) combines bombast with a grasp on history and firm confidence in his own views to craft an entertainingly over-the-top argument.

What You Should Know About Politics…But Don’t: A Nonpartisan Guide to the Issues That Matter, by Jessamyn Conrad
Modern American politics seem hopelessly partisan, and yet most people don’t think of themselves as partisan voters—they just want to know the plain, unadulterated facts in order to make a decision. But finding information that isn’t colored by partisan politics is difficult; bloggers, columnists, and commentators build audiences by appealing to partisan prejudices. Conrad offers a tonic: plain old facts that ignore political agendas, culture war talking points, or other fluff in favor of simply explaining what’s at stake, who supports what, and why it matters—leaving the ultimate decision of which side of an issue to support up to the reader (and voter), as it should be. If you plan to vote this year or at any time in the near future, this book is 100% required reading.

Whistlestop: My Favorite Stories from Presidential Campaign History, by John Dickerson
The political circus that descends on the country every four years has grown in size, volume, and chaos every election cycle—and yet what we see online and on TV is just the very tip of a very large iceberg. Dickerson, political commentator and moderator of Face the Nation, has been at the eye of most political storms over the years, and here he offers up the stories that reporters following campaigns tell each other over cocktails—intimate stories about last-minute Hail Mary speeches cooked up in hotel rooms, often hilarious mistakes made when standing in front of a microphone, and legendary stories only insiders have heard. It’s important to remember the people running for office are human beings with all the frailties all humans must deal with, and Dickerson masterfully drives that point home with stories about very capable people under very large amounts of stress as they vie for our votes.

Alter Egos: Hillary Clinton, Barack Obama, and the Twilight Struggle Over American Power, by Mark Landler
Politics makes for strange bedfellows, as the saying goes, and there are few stranger than Hillary Clinton and Barack Obama after the 2008 presidential election. After being bitter rivals for the Democratic nomination, Clinton and Obama joined forces on the campaign trail, and Clinton later joined Obama’s administration as his Secretary of State. Landler examines that relationship in detail, analyzing their different upbringings, generational ideas, and policies, and how their relationship went through various stages of trust and separation. Far from being in sync, Clinton and Obama differed on several major issues that his administration dealt with, and this book offers a clear, intimate examination of how two strong personalities at the pinnacle of power in this country worked together to forge domestic and foreign policies—a look that is vital for all voters as Clinton vies to succeed her former boss.

Trump and Me, by Mark Singer
Donald Trump has for a long time been someone almost beyond rational understanding, first as a real estate tycoon phase, later as a mock-proof reality TV star, and currently as the most unlikely presidential candidate for a major party ever. Back in 1996 Mark Singer got to spend a lot of unfiltered time with The Donald as he worked on a profile for The New Yorker—a profile that still earns Trump’s ire today. Singer recounts his time with Trump 20 years ago, offering a closeup analysis of the man and his psyche, and applies those observations to the man of 2016 who riles up crowds and says the most amazing things while ruling news cycles for weeks at a time. Whatever your opinion of Trump, this is a must-read for anyone who wants to understand the man who could be our next president.

Why the Right Went Wrong: Conservatism—From Goldwater to the Tea Party and Beyond, by E. J. Dionne, Jr.
No political movement happens in a vacuum, but often the roots of today’s headlines extend so far into the past they seem to arrive, fully formed, out of nowhere. Dionne, Jr., traces the origins of the modern-day Tea Party and its successors to the 1960s, especially the civil rights movement, President Johnson’s Great Society, and Barry Goldwater’s insurrection during the 1964 campaign. With a staggeringly encyclopedic knowledge of politics over the last 50 years, Dionne, Jr., analyzes how fringe voters and policies have migrated into the mainstream conservative movement even as the country as a whole drifted further to the left. With the political landscape of America in turmoil, it’s more important than ever to get a handle on the roots of modern-day politics.

Listen, Liberal: Or, What Ever Happened to the Party of the People?, by Thomas Frank
Smug ignorance, Frank argues effectively in this angry book, is a quality shared equally by both parties. Most famous for What’s the Matter with Kansas?, here Frank turns his clear-eyed anger on the Democratic Party, arguing forcefully and effectively that the supposedly “liberal” party must shoulder plenty of blame for the current state of affairs in America. Frank details how the Democrats have mutated into a party servicing an affluent, college-educated strata of liberal voters at the expense of the working class they once represented. His equal-opportunity dissection of political dysfunction in America is a welcome tonic for anyone who’s tired of all those “how to talk to your Republican uncle” think pieces out there.

It’s Even Worse Than It Looks: How the American Constitutional System Collided with the New Politics of Extremism, by Thomas E. Mann and Norman J. Ornstein
Mann and Ornstein offer a clear-eyed assessment of the harm stratified partisan politics are doing to the country, because our system of government was never designed to be partisan. They make the argument that as both political parties coalesce into parliamentary-style groups with rigid agendas and purity tests, the system of separated powers baked into the American system becomes less and less effective. In short, they say, the Constitution was designed for representatives more interested in running the country than political ideology. They then go on to offer solutions that would fix an often paralyzed system, leaving it to the reader to wonder whether any of their proposals would have a chance of being enacted in the modern world. Anyone who shakes their head in mystification every time the government shuts down or fails to pass what look like common-sense laws will find this book incredibly enlightening.