3. Naked Lunch (1991) The book almost borders on unreadable. There are themes running through the book but it isn't one that sells itself in the duration of an elevator ride. It's a long-form Beat poem and drug hallucination. It's a book that becomes lucid only in snippets. David Cronenberg is not a director to shy away from difficult material and took this challenge to heart. The way he wraps the story around biographical elements of William S. Burroughs' life is now the only way I can imagine it being done. Maybe not the best film on this list, not by a mile, but easily the most clever approach to adapting a difficult source.
2. The Lord Of The Rings (2001-2003) I'm going to cheat and include all three books and movies in this spot. I never would have believed I'd see a director try to adapt these books into single films. I certainly never thought they'd be among my favorite fantasy films of all-time. There's just too many characters, too many worlds, and too vast of a story to be told. Tolkien did Peter Jackson a favor by making the core story very focused and making many characters interchangeable. Much like the Harry Potter films (not on here because the adaptations seemed straight forward), I think we will live to see a day when they are remade into two films per book. You can already see that the current vogue of turning books into multiple films (Harry Potter, Twilight, Hunger Games and The Hobbit) would have served this franchise well ten years ago.
1. Watchmen (2009) It's hard to think of an adaptation of a book that I've held as the pinnacle of the Graphic Novel format. It's the book that for years has been used to "convince" people that comics are serious business. It appeals to intellectuals and just plain comic geeks. If you can write a book or teach a semester long class on a book, does it seem like it is a story that can be told in 150 minutes? I don't know if the movie made sense to people who hadn't read the Alan Moore comic book. You just can't divorce yourself from your own knowledge of backstory and interior monologue. Are the clues there or does the informed viewer find them because they know what to look for? I don't fault Zack Snyder's adaptation other than it delays what will ultimately have to be a 8-10 hour series to fully develop the story.