Douglas Adams — 42. Arthur Dent wakes up to find Earth about to be destroyed for an intergalactic superhighway. Who among us can’t say the same? Hijinx ensue. The perfect book to illustrate life’s inherent absurdities.
Richard Ben Cramer — Cramer makes the list based on one book alone, the remarkable What It Takes: The Way To The White House, a thorough chronicle of the 1988 presidential campaign. What It Takes covers six separate presidential candidates—including the first presidential campaign of one Joe Biden, who is apparently still around. It is a sprawling tale, masterfully told, though to pick it up today (my old hardback copy from high school is still on my shelves) is like reading a book about Cy Young: The sport is allegedly the same, but not really. He also wrote the definitive DiMaggio biography for extra points.
Franklin W. Dixon — Who? The pen name of a series of writers responsible for the Hardy Boys mystery series. I started reading these when I was, what, six or seven? I am sure I read all of the blue hardbacks and even many of the paperbacks that followed, until they gave way to Agatha Christie during the high school years.
Roger Ebert — I was a regular Siskel & Ebert watcher, and reading the review compendiums was not far behind. I will always remember the closing line of his Mad Dog Time review: “Mad Dog Time should be cut into free ukulele picks for the poor.” But he was as sharp and disciplined when reviewing the great movies. This insight into Casablanca is poignant: “Much of the emotional effect of Casablanca is achieved by indirection; as we leave the theater, we are absolutely convinced that the only thing keeping the world from going crazy is that the problems of three little people do after all amount to more than a hill of beans.”
David Halberstam — All of Halberstam’s writing is worth the read, but my seminal experience was with his book October 1964, which I read just as I was entering college. The book stands out as a great read, but I remember it to this day as possibly the first time in my life that I had thought seriously about issues of race in America. Though integrated with the addition of Elston Howard, the Yankees were still the team of Mantle, Maris, Kubek, and Ford, while the Cardinals featured African-Americans Bob Gibson, Lou Brock, Curt Flood, and Bill White (and pioneering Dominican infielder Julian Javier). Set against the 1964 Presidential election and the emerging civil rights movement, the book reminds that society itself is a change agent.
Hugh Hewitt — [Hahaha. Just kidding. Wanted to see if you were actually reading.]
Michael Lewis — Imagine a closed ecosystem where rats ran around a diamond-shaped maze for decades. Everyone watched the rats run around the maze, and some people even counted the number of times they ran around the maze. They had done this for so long that they assumed they understood everything there was to know about the maze and the rats. It turned out they knew little, if anything, about the maze, much less the rats, or what they were doing. The decade-ago debate over Moneyball—a debate that has long since been settled—obscured the far greater achievement: Moneyball chronicles how the powerful resist change, and so deny the need for it.
Rod Serling — The Fourth of July was always the Twilight Zone marathon on KTLA, and I always ran through the classic episodes. Even as a child, I recognized that not every story was about what the story was about. At that age, it was The Monsters Are Due on Maple Street, about a neighborhood that turns on each other after a series of unexplained events and To Serve Man, about a nine-foot alien race that lands on Earth making promises that are too good to be true. It took much longer and far more experience to appreciate the cautionary allegory of A Stop at Willoughby—a Serling-penned existential horror show anyone that’s taken one too many trains to nowhere might do well to avoid. I wish I had.
Rex Stout — And then I took some time off from the mysteries until I discovered my hero-muse, Rex Stout’s “one-seventh of a ton” agoraphobic detective Nero Wolfe. Stout’s mysteries were not intricate, but they were laced with recognizably human characters. Most of them are simply people that you would be happy to sit down and have a beer with—even the sometimes disagreeable lead character. Stout created a world that the reader could visit again and again, like seeing old friends you miss. Sometimes you even tell the same old stories, but it’s the joy of being together that matters. That’s what reading Rex Stout is like.
Bill Watterson — Watterson’s influence on American culture is remarkable for a man who drew a single comic strip, Calvin and Hobbes, for just one decade. But I read it everyday at the time, and every one of my children have read the collections when they were old enough to do so. Consider how much Watterson was able to do with room for only a handful of words in a single three or four-paneled strip. And how many comic strips make room for the words “salubrious,” “protozoan,” and “somnambulist?”
George F. Will — A reasoned thinker and economical writer, Will is one of the few political writers still worth reading. Even when he’s wrong, such as on term limits, his arguments are reasoned. And never unserious. Men At Work remains one of the great baseball books of all time.
Tom Wolfe — Consider the two most followed stories of just this weekend—the George Floyd protests and the Space X launch—then consider that Tom Wolfe wrote The Right Stuff in 1979 and The Bonfire of the Vanities in 1987. Then consider that if Sherman McCoy was a real person, he’d likely be Secretary of the Treasury right now. Perhaps he is. When I first read many years ago, under circumstances I cannot now recall, Wolfe’s observation that “every living moment of a human being’s life, unless the person is starving or in immediate danger of death in some other way, is controlled by a concern for status,” it read more like a personal challenge than an sociological observation. Either way, it is the single most trenchant observation about the human experience I have read, and will ever likely read.
Honorable Mention — William F. Buckley, Jr.; P. J. O’Rourke; Agatha Christie; Douglas Adams; CS Lewis; Stephen Sondheim; JRR Tolkien; P.G. Wodehouse; Ron Chernow; Lynne Olsen (on the strength of Troublesome Young Men alone); Stephen King; Howard Ashman; Hunter S. Thompson; Elmore Leonard; Brian Wilson; Joan Didion