The first Lovecraft story I read as a child was Pickman's Model. It absolutely scared the crap out of me. I didn't really get into his writing until highschool, where I used him as a topic for my senior year english research paper. I have all his stories, but sadly have not committed to reading all of them. I also love collecting the movies based on his work. Much like Lovecraft's written stories, even the bad movies have their charm.
I am re-reading Call of Cthulhu right now,
It really is interesting how Lovecraft can condense a story so well. Cthulhu is only some 20 pages long, but if adapted into a film, it would clock in at at least an hour and 40 minutes. It would be a great hour and 40 minutes in the right hands.
I would like to bring up one of my favorites. The Outsider. This is one of the saddest stories ever written, and I identify with the protagonist very well. Interesting given the ending of the story.
There was a 100% faithful adaptation of The Call of Cthulhu
made by the Lovecraft Historical Society. It is only a few years old, but black and white and silent and only clocks in at 47 minutes.
Also, if you like The Outsider, I recommend Stuart Gordon's Castle Freak
. It's a very loose adaptation, but it stars both Barbara Crampton and Jeffrey Combs (more widely known for starring in Re-Animator and From Beyond).
also of interest for any Lovecraft fan... Alan Moore's Neonomicon wich i've been reading and loving.. is based on Lovecraft's mythos... and has a few interesting observations on what Alan thinks Lovecraft is really all about...
I loved the first issue of Neonomicon, but I don't like the overtly sexual tone that Moore has attached to the mythos. Lovecraft was almost entirely asexual, and had a deep phobia of sexual relations. Moore's fascination on sex feels to me like an attempt at shock value, something easily attained in the 1920's with unnamed horrors with tentacles.