Wonder Boys by Michael Chabon
I loved The Amazing Adventures of Kavalier and Clay, and was disappointed with The Mysteries of Pittsburgh. I remembered enjoying the film Wonderboys so I figured if I was going to give Chabon another try, that was probably the novel to go with.
The physical description of the main character and narrator sounds nothing like Michael Douglas, although I remember liking his role in the film. Same with Hannah and Katie Holmes. Overall, I liked the book - I couldn't believe how much pot Grady smoked, though.
Grady is an author, working at a college in New England. He has been working on his new novel for seven years, and is nowhere near finishing it, despite being at over 2000 pages. His third marriage is ending, he is having an affair with the chancellor who is also the head of the English department's wife, and she has just told him that she is pregnant. Instead of dealing with all these issues, Grady starts hanging out with an odd and slightly depressed student, which leads to a few dead pets (never leave an animal anywhere near Grady would be the lesson in this one) and really bad road trip moments.
It's actually funny, although Grady is just ridiculous at times - at 41, he has somehow avoided growing up. It really starts sinking in how much of a disappointment he has become as he deals with his editor and best friend, his third wife, his girlfriend and his admiring students, such as James and Hannah, who become slightly disillusioned with him.