Steven Sassaman

The rules: I’ve chosen only one novel per author to put on the main list, while identifying other worthwhile books by those authors as “honorable mentions.” This is highly unscientific – some honorable mentions are better books than list members (Emma is a better book than Vanity Fair) – but yields are more widely ranging list than one dominated by books from a small number of authors. The ordering is also extremely approximate. Nos. 1-3 clearly belong in those slots but after that there are plenty of ties. So for Nos. 4-X, the ranking is far less precise.

1. Anna Karenina – Leo Tolstoy (1877)

This is probably the greatest novel ever written. It’s most famous for its central story of doomed and adulterous love but that’s actually the least interesting part. The book weaves together three different threads: a conventional novel of love and manners among the upper-middle class and petty nobility in pre-revolutionary Russia; a philosophical meditation on how to foster justice and good in the world; and insightful examination of characters’ internal worlds. The last is what’s best and most modern about this novel.

Tolstoy laid the ground for the naturalistic and stream-of-consciousness fiction of the early 20th century, brilliantly and insightfully exploring how actual people experience life minute-by-minute. Ever felt horribly out of place at a party? Tolstoy explores how someone tries to survive that discomfort. Have you admired the free and easy life of a friend? The author delves into what happens when you realize that the friend’s life isn’t much better than your own – disappointment, disillusionment, and resignation. Have you ever known that you’re being unreasonable and alienating the people around you, but couldn’t stop yourself? Tolstoy explored that as well.

Anna’s adulterous journey gives the novel its narrative drive but what you’ll remember most is how perfectly it captures the messiness of real life and real people. No one is a true hero and no one is an actual villain: we’re all just trying to get through life as best we can. A pretty radical sentiment for the 1870s, no?

Honorable mentions: War and Peace (Truly remarkable in its scope and ambition, but the scale of the novel often dwarfs its individual characters.)

Cross-media Recommendation: The song “Tolstoy” from Welcome to My Century by Bob Hillman (available on iTunes). It’s a fabulous contemporary folk album with clever lyrics but this track really stands out Hillman is clearly a Tolstoy fan and perfectly captures how the author’s insights can describe the messy emotions of contemporary hipsters as well as those of 19th-century Russian aristocrats.