Designing for the deceased
Marie Mundaca designed three of David Foster Wallace's books (the insides, not the covers). The second one was challenging but rewarding.
Wallace's idea was to have leaders and labels, like a diagram. He wanted something that looked like hypertext rollovers that were immediate and at hand. I thought this whole thing might be a bit much for me to design. It seemed like it might be a full-time job. I sent it off to one of my favorite designers, who shot me an email back saying something along the lines of "There is not enough money in the world to make me do this."
The third was just plain tough.