Trash Robinson at the A.V. club has an interesting post on Stephen King geeks. The theme is interesting: Because King has built an entire subculture, it can be difficult for newbies to break in to reading King.
Their argument is that it is hard to understand King because his books are so large and intertwined with one another and the Dark Tower series. You kinda have to be a geek to understand it all. (I like King, but I certainly don't understand all of the bridges between books. But I enjoy reading those who do understand. Bev Vencent in particular.)
They suggest starting to read King by picking up a copy of his short stories, Skeleton Crew. While I agree that King can be hard to get into, you don't really have to make a "plan." I started with the Stand, and was hooked ever sense. A.V. says:
By any route, though, new King fans should eventually arrive at The Stand, King’s standalone classic (to the degree that any of his books stand alone, given the threads and references that connect them) about the post-apocalyptic battle between good and evil. If not for its length, The Stand might itself be the best place for new King readers to start: The first half is firmly set in a real world of small towns, pathogens, and a speculative consideration of exactly how American society would fall apart if a bioengineered super-virus wiped out 99 percent of the Earth’s population. The supernatural elements that eventually turn the book into a cosmic battleground are introduced gradually, and the real-world grounding never entirely lets go. The Stand is a vast, leisurely book full of memorable characters, and it lacks the propulsion of his smaller novels, but it builds a world big enough to get lost in.