I think remaking a classic is bad territory to tread on. In the end, the classic version will always be seen as the better one, because it is instilled into people's hearts and minds. A lot of the time people remake a movie without being blatantly obvious of it. I saw a movie that combined It's a Wonderful Life and Groundhog's Day. While it was not as good as either film, it didn't do it in a way that made it a complete rip off.
In some cases a remake of a classic that was based off of a classic novel is a good idea, like True Grit. Then you have remakes of a classic that was based off of a classic novel that becomes a travesty, like Willy Wonka.
If you can improve upon the subject material to a great degree, and still have originality, you will do well.
In 1997 there was a mini series that closely followed Stephen King's The Shining. While it made many of the book's fans foam at the mouth, it wasn't as interesting as Kubrick's film. It works as a mini series, but would fail as a film. In the end a book is something you can enjoy over a period of several hours, but it would be uncomfortable and boring to do in film.
The film version of a book should be a "Highlights" set up. In the end, a film editor does that job better than even the director. You cut out all the fat, you focus on the core of the story, and you tell it in the best way possible, you have a great film. So, while Stanley Kubrick didn't have every single moment and piece of dialogue in his film, (It would have been boring thanks to King's need to jaw), he made the film his own, and it was great.
Only the greats have been able to do this. Kubrick and as of recent The Coen Brothers. These are story driven movies. Take out the dialogue, and they are just as good.