Update: Thanks AlexanderHammil! I was totally thinking of John Bellair's books. And they were illustrated by Gorey. Time to hunt down copies of these to own and pass on to my kids.
Odeckers, I'm hoping to get your help hunting down a series I loved in my childhood.
(Mods - let me know if this is too off topic and I shall delete).
The series focuses on a boy and the various adults in his life (uncle? father?), and they encounter all sorts of strange, almost macabre situations. The covers were all black and very gothic, along the vein of Edward Gorey. The characters had the signature style of the roundish face with a prominent nose. (Picture NOT from the books, just an example). Not sure if it's him though, since a quick googling didn't turn up the series. If anyone knows what series this is, you will have my eternal gratitutde!
Side note: This also reminds me of the series of short stories from Paul Jennings which I also loved.
One that really stuck in my head (synopsis from Wikipedia):
Nails: A boy gets stranded on an island with his father. But he has three other problems: one, he has never seen his mother; two, he is forced to watch his father die; and three, he has nails growing all over him.
They didn't give me nightmares, but they did leave that wonderful, tingly feeling that there are strange, strange things in the universe. Feel free to share any childhood favorites that also leave you with that delicious, creeped out feeling =P