Books That Go Together

I'm vacationing this week, staring out over beautiful stretches of water, thinking about books that go together. I packed with me Moby Dick, by Herman Melville, and Why Read Moby Dick? by Nathaniel Philbrick, but I haven't started either because I can't seem to decide which I should read first.

When I first read Anna Karenina, I started with the introduction. It was called the introduction, and I expected it to introduce me to the text. Instead, it gave away the outcome of the story--and turned me off of classics introductions forevermore.

But when I read Jane Austen's Emma, I started with the essay on the novel in A Jane Austen Education, and found that I ultimately took more away from Austen's novel than I might have without the essay introduction. (That being said, I still didn't enjoy the novel, and find I'm not so much of an Austen fan.)

Now I'm staring down Moby Dick and Why Read Moby Dick?, uncertain of where to start, and wondering about books that go together, and whether reading about a book enhances the reading of it, or whether reading about a classic is more impactful if you've already read the classic being discussed:

• Lolita and Reading Lolita in Tehran
• The Great Gatsby and So We Read On
• Jane Austen's novels and A Jane Austen Education

That's not even taking into consideration books about an author's life (such as Hemingway's Boat), novels that reinvent an author's life (Z: A Novel of Zelda and Call Me Zelda come to mind), or modern retellings of classic novels (Great, Song of Achilles).

What do you think? Where should I start?