100 Books Every Middle-Aged Man Should Read
Being comfortably in middle age, something I’ve wanted to do for years is conquering one of those 100 books everyone should read lists. They’re all over the internet, from Esquire, to Business Insider, and everywhere in between.
Problems, Problems, Problems
The problems for me though are myriad. First, I’m a slow reader. Sometimes it takes me several weeks to slog through a book that’s easy to read, let alone a magnum opus like The Brothers Karamazov or Don Quixote, which could take several months. At that rate I’d spend the rest of my life and only make it halfway through the list.

Secondly, like many people, I don’t have an endless amount of time to devote to reading. I have a wife and kids and I can’t lock myself away night after night for years on end just to read. Something had to give, and up to this point in my life, it’s been reading.
Still, I’m determined to enrich and empower and educate myself, and there is no better avenue to accomplish those goals than reading. A while back I attempted something similar, challenging myself to read twenty books in a year. I failed miserably. I barely finished five books and found myself disgusted by the lack of commitment to my goal.
Solutions
The following year, I challenged myself again, this time upping the ante to twenty-five books. The difference was I wasn’t going to read the books, but I was going to listen to them instead, on Audible.com.
This solved two of my biggest problems. First, listening helped me avoid the problems associated with slow reading. When I read, my mind can wander, and I end up flipping through pages and reading different passages over and over. When all I’m able to do is listen, this problem is eliminated. My mind stops wandering to concentrate on what’s being said. Plus, there’s no easy way to go back and read sections repeatedly.
Listening instead of reading allows me to do two things at once. My day typically starts with a thirty-minute walk. Instead of just walking, I realized I can “read’ as well. I also take Dublin, my black Labrador Retriever, for several walks a day. That adds even more time to read.

Driving While Listening
I also have a job that requires a lot of driving. Instead of listening to mindless sports radio debates, I began listening to audio books. This added another five hours per week to my “reading” time with no other cost.
Overall, I had about ten hours a week where I could “read” that didn’t stop me from doing things I was already doing. Listening to audio books allowed me to effectively multi-task. This allowed me to achieve my goal of finishing twenty-five books in a single year.
Part of me thought listening instead of reading was cheating. I felt guilty that I was listening instead of putting my head down and doing the challenging work of reading. Studies have shown however, that when it comes to comprehension there isn’t any significant difference between listening and reading. For my goals of enriching and educating myself, I didn’t see any point in making a distinction.
The Plan
With that thought in mind, I put together a five-year plan to listen to 100 books. That works out to twenty a year, and since I’d already listened to twenty-five in a year once before, that seemed like a realizable goal.
The next step was choosing 100 books to read. Most book lists I’d come across included a number of classic books that I’d read in high school and college. I had no interest in re-reading any books, so this eliminated twenty or so books from most existing lists right off the bat.

Culling together titles from a number of sources, I finally produced my very own list of 100 books to listen to. I like to think my list covers a wider gamut of books than most other lists out there. My list includes a fair share of classics, but also includes history, memoirs, and other types of non-fiction books. Modern books are part of my list as well. While some of these books might not be viewed as classics today, hopefully in time they will. Overall, my list is quite diverse and well-rounded, and hopefully will allow me to broaden my horizons and expand my point of view over the next five years.
The Final List
One other thing, my list turned out to be 106 books. I found drawing the line and keeping it to just 100 hard to do. As I start reading these books, if the inspiration strikes or if I feel like I have insight to share, I do plan to offer additional commentary on this blog.
Without further ado, below is my list of 106 books to listen to over the next five years.
106 Books Every Middle-Aged Man Should Read
# | Title | Author | Type | Duration |
1 | 1984 | George Orwell | Novel | 11:22 |
2 | A Brief History of Time | Stephen Hawking | Non-Fiction | 5:46 |
3 | A Confederacy of Dunces | John Kennedy Toole | Novel | 13:32 |
4 | A Game of Thrones | George R.R. Martin | Novel | 33:46 |
5 | A Good Man is Hard to Find | Flannery O’Conner | Short Stories | 7:36 |
6 | A Heartbreaking Work of Staggering Genius | Dave Eggers | Memoir | 13:28 |
7 | A People’s History of the United States | Howard Zinn | History | 34:08 |
8 | A Scanner Darkly | Philip K. Dick | Novel | 9:12 |
9 | A Separate Peace | John Knowles | Novel | 6:08 |
10 | A Visit from the Goon Squad | Jennifer Egan | Novel | 10:07 |
11 | A Wrinkle in Time | Madeleine L’Engle | Novel | 6:27 |
12 | All the President’s Men | Bob Woodward | Memoir | 12:55 |
13 | American Pastoral | Philip Roth | Novel | 15:05 |
14 | And Then There Were None | Agatha Christie | Novel | 6:01 |
15 | Anna Karenina | Leo Tolstoy | Novel | 35:35 |
16 | Battle Cry Freedom | James Macpherson | History | 39:40 |
17 | Beloved | Toni Morrison | Novel | 12:03 |
18 | Brave New World | Aldous Huxley | Novel | 8:00 |
19 | Chronicles: Volume One | Bob Dylan | Memoir | 5:49 |
20 | Crime & Punishment | Fyodor Dostoevsky | Novel | 20:28 |
21 | David Copperfield | Charles Dickens | Novel | 33:54 |
22 | Don Quixote | Miguel de Cervantes | Novel | 39:37 |
23 | Drinking Coffee Elsewhere | Z.Z. Packer | Short Stories | 6:50 |
24 | East of Eden | John Steinbeck | Novel | 25:23 |
25 | Edgar Allan Poe: The Complete Short Stories | Edgar Allan Poe | Short Stories | 16:34 |
26 | Emma | Jane Austen | Novel | 18:25 |
27 | Factotum | Charles Bukowski | Novel | 5:08 |
28 | Faust | Johan Wolfgang von Goethe | Novel | 12:45 |
29 | Fear and Loathing in Las Vegas | Hunter S. Thompson | Memoir | 6:00 |
30 | Fear of Flying | Erica Jong | Novel | 11:45 |
31 | Fifty-Two Stories | Anton Chekov | Short Stories | 20:13 |
32 | For Whom the Bell Tolls | Ernest Hemingway | Novel | 16:17 |
33 | Friend of My Youth | Alice Munro | Short Stories | 10:03 |
34 | From Here to Eternity | James Jones | Novel | 36:50 |
35 | Goodbye to All That | Robert Graves | Memoir | 4:58 |
36 | Harry Potter and the Sorcerer’s Stone | J.K Rowling | Novel | 8:18 |
37 | Hatchet | Gary Paulsen | Novel | 3:42 |
38 | Housekeeping | Marilynne Robinson | Novel | 6:24 |
39 | How to Win Friends and Influence People | Dale Carnegie | Non-Fiction | 7:15 |
40 | In Cold Blood | Truman Capote | Non-Fiction | 14:27 |
41 | Jane Eyre | Charlotte Bronte | Novel | 19:10 |
42 | Kidnapped | Robert Louis Stevenson | Novel | 7:20 |
43 | Kim | Rudyard Kipling | Novel | 11:54 |
44 | King Solomon’s Mines | H. Rider Haggard | Novel | 8:27 |
45 | Lady Chatterly’s Lover | D.H. Lawrence | Novel | 13:05 |
46 | Less Than Zero | Brett Easton Ellis | Novel | 5:37 |
47 | Lolita | Vladimir Nabokov | Novel | 11:28 |
48 | Lullaby | Chuck Palahniuk | Novel | 7:15 |
49 | Midnight’s Children | Salman Rushdie | Novel | 24:29 |
50 | My Life | Anton Chekov | Novel | 3:57 |
51 | Never Let Me Go | Kazuo Ishiguro | Novel | 9:40 |
52 | Of Human Bondage | W. Somerset Maugham | Novel | 25:53 |
53 | One Hundred Years of Solitude | Gabriel Garcia Marquez | Novel | 14:04 |
54 | Over the Edge of the World | Laurence Bergreen | Non-Fiction | 6:13 |
55 | Perfume | Patrick Suskind | Novel | 9:00 |
56 | Seven Habits of Highly Effective People | Stephen R. Covey | Non-Fiction | 13:04 |
57 | So Long, See You Tomorrow | William Maxwell | Novel | 6:02 |
58 | Stranger in a Strange Land | Robert A. Heinlein | Novel | 16:17 |
59 | Team of Rivals | Doris Kearns Goodwin | History | 41:32 |
60 | Th Brothers Karamazov | Fyodor Dostoevsky | Novel | 43:06 |
61 | The Adventures of Augie March | Saul Bellow | Novel | 22:13 |
62 | The Adventures of Huckleberry Finn | Mark Twain | Novel | 9:44 |
63 | The Alchemist | Paulo Coelho | Novel | 4:00 |
64 | The Amazing Adventures of Kavalier & Clay | Michael Chabon | Novel | 26:20 |
65 | The Autobiography of Benjamin Franklin | Benjamin Franklin | Memoir | 6:35 |
66 | The Best and the Brightest | David Halberstam | History | 37:04 |
67 | The Corrections | Jonathan Franzen | Novel | 21:53 |
68 | The Crossing | Cormac McCarthy | Novel | 14:41 |
69 | The Crying of Lot 49 | Thomas Pynchon | Novel | 6:14 |
70 | The Executioner’s Song | Norman Mailer | Non-Fiction | 42:37 |
71 | The Guns of August | Barbara W. Tuchman | History | 19:09 |
72 | The Hitchhiker’s Guide to the Galaxy | Douglas Adams | Novel | 5:51 |
73 | The Hunchback of Notre Dame | Victor Hugo | Novel | 22:15 |
74 | The Killer Angels | Michael Shaara | Novel | 13:44 |
75 | The Kite Runner | Khaled Hosseini | Novel | 12:01 |
76 | The Liars’ Club: A Memoir | Mary Karr | Memoir | 4:08 |
77 | The Lion, The Witch, and the Wardrobe | C.S. Lewis | Novel | 4:21 |
78 | The Long Goodbye | Raymond Chandler | Novel | 13:25 |
79 | The Maltese Falcon | Dashiell Hammett | Novel | 7:05 |
80 | The Moonstone | Wilkie Collins | Novel | 18:45 |
81 | The Naked and the Dead | Norman Mailer | Novel | 26:14 |
82 | The Picture of Dorian Gray | Oscar Wilde | Novel | 8:35 |
83 | The Right Stuff | Tom Wolfe | History | 15:42 |
84 | The Rise and Fall of the Third Reich | William L. Shirer | History | 57:11 |
85 | The Secret History | Donna Tartt | Novel | 22:03 |
86 | The Selfish Gene | Richard Dawkins | Non-Fiction | 16:12 |
87 | The Sound and the Fury | William Faulkner | Novel | 8:51 |
88 | The Spy Who Came in From the Cold | John le Carre | Novel | 7:00 |
89 | The Stand | Stephen King | Novel | 47:47 |
90 | The Stranger | Albert Camus | Novel | 3:27 |
91 | The Sun Also Rises | Ernest Hemingway | Novel | 7:46 |
92 | The Thirty-Nine Steps | John Buchan | Novel | 3:53 |
93 | The Three Musketeers | Alexandre Dumas | Novel | 23:32 |
94 | The Trial | Franz Kafka | Novel | 8:53 |
95 | The Wealth of Nations | Adam Smith | Non-Fiction | 36:43 |
96 | The Wind-Up Bird Chronicle | Haruki Murakami | Novel | 26:11 |
97 | The Year of Magical Thinking | Joan Didion | Memoir | 5:05 |
98 | This Boy’s Life | Tobias Wolff | Memoir | 10:01 |
99 | To the Lighthouse | Virginia Woolf | Novel | 6:37 |
100 | Tropic of Cancer | Henry Miller | Novel | 10:01 |
101 | Ulysses | James Joyce | Novel | 27:16 |
102 | Underworld | Don DeLillo | Novel | 31:22 |
103 | Valley of the Dolls | Jacqueline Susann | Novel | 17:39 |
104 | Waiting for Godot | Samuel Beckett | Play | 2:02 |
105 | White Teeth | Zadie Smith | Novel | 18:38 |
106 | Wuthering Heights | Emily Bronte | Novel | 12:32 |