Treatment Kind and Fair: Letters to a Young Doctor by Perri Klass (Basic Books, 2007)
Naked by David Sedaris (Back Bay Books/Little, Brown and Company, 1997)
Dress Your Family in Corduroy and Denim by David Sedaris (Little, Brown and Company, 2004)
Barrel Fever: Stories and Essays by David Sedaris (Back Bay Books/Little, Brown and Company, 1994) [though in reality I'd more strongly recommend the essays, especially "SantaLand Diaries"]
Instead of linking these books anywhere, I'm going to take an opportunity to recommend IndieBound, which has a pretty slick Indie Store Finder located at http://www.indiebound.org/indie-store-finder.
Now, a few movies:
The Painted Veil, based on the novel by W. Somerset Maugham, directed by John Curran and starring Edward Norton and Naomi Watts as Walter and Kitty Fane.
Synecdoche, New York, written and directed by Charlie Kaufman and starring Philip Seymour Hoffman as Caden Cotard, Catherine Keener as Adele Lack, Samantha Morton as Hazel, and about a thousand other people. Maybe literally. This movie was huge in scope and subject matter, though maybe you could boil it down to a discussion of the meaning of life and death. I found it a little intense.
Lost in Translation, written and directed by Sofia Coppola and starring Bill Murray as Bob Harris, Scarlett Johansson as Charlotte, and Giovanni Ribisi as John, Charlotte's husband. I saw this again recently. It didn't have quite the same effect this time, largely because I had seen it before, I think, and knew where it was going. But I still think that Sofia Coppola very effectively recreated the quiet, lonely world that seems so intimately entwined with extended bouts of insomnia.