I think Crime and Punishment intimidated me because I had heard Dostoyevsky was hard to read AND it was long, but honestly it wasn't that long, and I don't find him hard to read at all. That was a page-turner to me. After that I decided to explore classics more and not to let "hard" reputations intimidate me. The most difficult books I've read have been Ulysses by James Joyce (needed a lot of support for that one in the form of online analyses and stuff), Infinite Jest by David Foster Wallace, War and Peace by Tolstoy, and The Sound and the Fury by William Faulkner. I still have Gravity's Rainbow by Thomas Pynchon yet to tackle. :) I am not be reading these at the comprehension level of an English professor, but the good thing about the classics is their many layers and how you can get so much out of them the more in-depth you dive. Honestly I hope I live long enough to have time to re-read and re-read these.

Some favorites are:

Of Human Bondage by W. Somerset Maugham, Far From the Madding Crowd by Thomas Hardy, Moby Dick and House of the Seven Gables by Herman Melville, Pride and Prejudice and Persuasion by Jane Austen, Portrait of a Lady by Henry James, Anna Karenina by Tolstoy, Notes From Underground by Dostoyevsky, Howard's End and Maurice by E.M. Forster, He Knew He was Right by Anthony Trollope, A Tale of Two Cities by Charles Dickens, and The Count of Monte Cristo by Alexandre Dumas...

For more modern classics, anything William Faulkner although my favorites are The Sound and the Fury, Absalom, Absaolm, the Unvanquished, and Flags in the Dust, James Baldwin (Another Country, Giovanni's Room, and If Beale Street Could Talk are my faves), Toni Morrison (can't pick a fave, everything of hers I've read has been amazing), Their Eyes Were Watching God by Zora Neale Hurston, Native Son and The Man Who Lived Underground by Richard Wright...

I could go on and on (actually I guess I DID go on and on) but those are some top picks. I'm currently reading Jazz by Toni Morrison and I was up super late last night because I just couldn't put it down.