The 5 Books I’ve Reread the Most

In an ideal world, I would reread all of the books I consumed during my formative years in high school. I’d find new layers and previously undiscovered insights and marvel at just how much I’ve grown intellectually. The only problem—and as far as problems go this is a nice one to have—is there are just too many good books out there! Since my brain is permanently stuck on the “scatter” setting, I’m currently in the middle of reading four different books—all of which I ignored last week because something titled Sharknado was on television. Sharks and tornadoes? Together?! Take the night off, Hemingway, because I need to see how this situation out.

I do spend some precious time rereading, though; here are the five books I’ve returned to again and again.

5. Live From New York: An Uncensored History of Saturday Night Live, by Tom Shales & James Andrew Miller (three times). I love devouring a compelling oral history book. It’s like sneaking a peak at a more interesting person’s high school yearbook. The fact that I read this detailed history of Saturday Night Live three times might not seem too impressive, but this comprehensive history weighs in at just under 600 pages of tantalizing late night gossip. It’s also a great reference source. Its conversational tone and unintimidating, abbreviated storytelling structure lends itself to spontaneous reading sessions when you merely set out to find out the joke that instigated the David Spade/Eddie Murphy feud.

4. Killing Yourself to Live, by Chuck Klosterman (four times). On the surface, this Klosterman classic should be nowhere near my top five most read books. A nonfiction story that’s ostensibly about a “famous deaths of rock ‘n roll road trip” doesn’t seem particularly interesting to someone who once—and possibly still—believed that a conversation regarding musical supremacy must include the words Counting, Gin, and Matchbox, but Killing Yourself to Live is more about the journey and less about the destination. Hidden within the morbid hook is a thought-provoking tale about people, love, and our expectations regarding both. If you’re someone who has an old shoebox full of movie stubs and summer camp letters buried deep in your closet, chances are you’ll appreciate the nostalgic nature of Killing Yourself to Live.

3. My Custom Van, by Michael Ian Black (four times).

My Custom Van isn’t my favorite Michael Ian Black book—that would be his equal parts touching and hilarious memoir You’re Not Doing it Rightbut it is one of the smartest collection of comedic essays ever assembled. Plus, books containing a multitude of small, humorous stories are ideal companions for both the busy professional on the go and the man who loves to nap! With titles like, “What I Would Be Thinking If I Were Billy Joel Driving to a Holiday Party Where I Knew There Was Going to Be a Piano” and “Vampires—Good for the Economy?” this eclectic collection of clever setups and witty musings contains laugh out loud passages for everyone, no matter how offbeat your comedic proclivities may be.

2. The Catcher in the Rye, by J.D. Salinger (six times).

While this J.D. Salinger classic is a personal favorite of mine, I probably wouldn’t have read it as many times as I have if it weren’t the only book left in my childhood bedroom. Every year, after I invariably finish whatever book I brought home over Christmas break, I’m left with the choice between Holden Caulfield and my 7th grade journal. It’s entertaining to revisit my youthful confusion about women and the difference between “there” and “their,” but Caulfield’s adventures in New York City usually wins out.

1. The Winter of Our Discontent, by John Steinbeck (eight times).

The story of how a person discovers his favorite book should be a magical one. Maybe it was a gift from a high school sweetheart or a mentor. The point is, it should be a tale worthy of the significance of the book. I am both horrifically embarrassed and surprisingly amused by the fact that I discovered my favorite book by watching Chad Michael Murray squint his way through the angst-ridden tribulations of life, love, and basketball on One Tree Hill. My copy of The Winter of Our Discontent looks the way I feel when someone walks in on me watching One Tree Hill–tethered, with the cover (my dignity) barely hanging on by a thread.

What are some of your favorite books to reread?

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