Wonder Boys by Michael Chabon
Re-reading this for maybe the third or fourth time: funny and sad and funny again. A happy ending with a wedding, so by Shakespeare's rules that makes it a comedy. The movie is actually well done (Michael Douglas shlubbing around in a woman's pink chenille bathrobe is iconic) but there are are layers and back story you'll only get from the book.
Yes, it's embarrassing how many times my inner life corresponds with Grady Tripp's, but that could be said for any middle-aged writer, teacher or former Wonder Boy. I don't smoke dope like Grady, and I don't have my boss's dead dog, a dead boa constrictor and a tuba in my car trunk-- but the butt-cheek impression left by a James Brown impersonator in the hood of my car is not outside the realm of possibility.