So in response to his "contest" (who can't resist that?) here are my ideas for his prompts:
The Little Prince, The Alchemist, Jonathon Livingstone Seagull, The Phantom Tollbooth are all "quirky" yet thought provoking reads. Here's a great list of books I just came across, many of which I've read and have found inspiring and many I see that I'd like to still read (Zen and the Art of Motorcycle Maintenance for one).
2. "A movie that illicts thought, reflection or emotion" The Green Mile, Life is Beautiful, Gran Torino and Amelie are a few that come to mind.
For 3. "Attend a Cultural Event" and 4. "Learn or demonstrate a life lesson" maybe add "....that is out of your comfort zone".
While these bonus assignments I'm assuming are to give students a chance to bring their mark up as much as possible (most likely to fulfill the expectations of parents and future educational instutitions), I love the idea that along the way they might just stumble upon an experience that is rewarding in itself. Good luck with that Mr. W!
...and if anyone else has some good ideas, let me know and I'll pass them along.