Dead End Follies and you should all check it out.
Here are my TENTATIVE selections:
Hardboiled Classic: Chandler, The Big Sleep
Noir Classic: Cain, Double Indemnity
Prison Book: Margaret Atwood, Alias Grace
Book Written by a Writer that has Done Time: Kesey, One Flew Over the Cuckoo's Nest
Book with a Psychopath Protagonist: F
Gothic Novel: Tartt, The Secret History
Classic Novel Whose Plot Revolves Around a Crime: Capote, In Cold Blood
The "Why the HELL am I Getting Myself Into This" Book: I don't know yet. Maybe a Russian. Maybe Pynchon or DFW.