1. The Making of the President 1960 (Theodore White)
A book chronicling the captivating race between Nixon and Kennedy in the titular election year. Considered by some to be the starting point for modern political journalism, you know, no big deal or anything.
2. The Selling of the President: The Classical Account of the Packaging of a Candidate (by Joe McGinnis)
A story about the 1968 election that shows how modern politicking came to be — and proposes some pretty heavy suggestions about why Americans pick one candidate over the other. A must-read for future space elections, where we will vote on candidates based on the humor-value of their memes.
3. Quest For The Presidency 1992 (Peter Goldman and the Newsweek Special Election Team)
The true story of the 1992 election, as told by a team of Newsweek reporters with unprecedented access to the various parties involved in the campaigns. It’s just a happy coincidence it was the same year that Batman Returns came out in theaters.
4. Boys on the Bus (by Timothy Crouse)
Rolling Stone reporter Timothy Crouse jumps around the country following both the McGovern and Nixon campaigns from 1972, before it was as cool as following around Blue Oyster Cult.
5. Fear and Loathing on the Campaign Trail (by Hunter S. Thompson)
A campaign book by Hunter S. Thompson? What more information do you need? It’s one of the best-selling campaign novels of all time. It’s the book that had The New York Times calling Thompson “the flamboyant apostle and avatar of gonzo journalism.”
6. The Great Derangement and Smells Like Dead Elephants (by Matt Taibbi)
A pair of excellent books from Rolling Stone’s Matt Taibbi. The Great Derangement focuses on the madness of Bush-era post 9/11 America, and Smells Like Dead Elephants is a collection of the best of Taibbi’s “Road Work” column from Rolling Stone.
7. What It Takes: The Way To The Whitehouse (by Richard Ben Cramer)
AN exploration of the mix of characteristics necessary for a presidential candidate — ambition, determination, and maybe more than a dash of insanity. Stir vigorously. Do NOT let it boil.
8. Losers: The Road To Everyplace but the White House (by Michael Lewis)
A look at the 1996 campaign trail that takes a look at the absurd process of the modern American election, and wonders if all the willing participants in the nonsense — from journalists to the voters themselves — are just a bunch of losers.
9. Tanner ‘88 (directed by Robert Altman, written by Gary Trudeau)
It’s not a book but it deserves to be here. The 1988 political mockumentary series is a great look at the insanity of the American campaign trail, written by the biting politically charged voice behind the Doonesbury comic strip.
10. Poisoning The Press: Richard Nixon, Jack Anderson, and the Rise of Washington’s Scandal Culture (by Mark Feldstein)
“Poisoning The Press” is a study on the feud between Nixon and newsman Jack Anderson, which included countless scandals of bribery, burglary, public smearing, and even a rumored assassination attempt.
11. The Dark Side Of Camelot (by Seymour Hersh)
An in-depth look at the Kennedy White House and the man himself, meticulously detailed and intensely controversial at the time of publication. It’s worth noting that the publication was relatively recent, so it’s 1998 controversial, not, like, 1970s controversial.
12. American Tabloid (by James Ellroy)
Ellroy details an incredible view of the American underworld from the late 1950s to the assassination of JFK. It’s probably easier to read this book than watch the myriad of movies that focus on bits and pieces of the story.
13. Miami and the Siege of Chicago (by Norman Mailer)
A provocative look at the year 1968, which saw many moments of unrest in recent American history, including the assassinations of Martin Luther King Jr. and Bobby Kennedy, and riots across the entire country. Also, NORMAN MAILER. Dude’s a legend. Co-created the Village Voice. One of the founding fathers of “New Journalism.”