Shirley Jackson: Novels and Stories, edited by Joyce Carol Oates (2010). This was not a poor investment.
This jam-packed volume includes Jackson's short story collection, The Lottery, the aforementioned The Haunting of Hill House, We Have Always Lived in the Castle (which I'd also borrowed and read before), and a set of other stories and sketches, some published during Jackson's lifetime and others published posthumously by her husband. Topping it all off is a chronology of Jackson's life and notes for all the collected works. I really really liked Jackson when I had previously read these two novels, I'm now a Jackson worshiper after reading her short stories. So amazingly good. Here's the book-by-book run down:
The Lottery (1949)
I'd read the title story from this collection before, like many people, in high school (and possibly again in college). It was just as unsettling as the first time I read it, but its perspective and tone is different from the bulk of Jackson's short stories which tend to be more realistic (although just as biting) and focused on an individual instead of a whole group. Some of my favorites in the collection are the irrepressible "My Life with R.H. Macy," "Elizabeth," "Pillar of Salt," and the extremely creepy horror show that is "The Tooth."
Jackson deals expertly and pointedly with issues of race, domesticity, gender, isolation, and depression. And no one does the creepiness of being an outsider in a small town or a rube in the big city quite like she does.
The Haunting of Hill House (1959)
I reviewed this one earlier here, so I won't rehash what I said before except to add that for some reason the character of the doctor's wife really irked me this time -- I felt like her brash comic relief really derailed the psychological claustrophobia of being in Eleanor's head and could have used a lighter touch. Still, this story is pretty darn excellent.
We Have Always Lived in the Castle (1962)
And I reviewed this one here. I liked it even more the second time -- this could quite possibly be a perfectly constructed novel.
Other Stories and Sketches (1938-1965)
Some of these are a little lighter than Jackson's other work and are representative of her successful career publishing essays and stories in various magazines. Others, however, are creepier than anything else. I particularly liked "The Summer People," "A Visit," "Louisa, Please Come Home," and the story that gives "The Tooth" a run for its money, "The Bus."
It really doesn't matter where you start with Shirley Jackson, just go ahead and get started. The other day I bought a couple more of her novels, so don't be surprised when you see her around here again. She is quickly moving up to my favorite authors of all time list.