I kind of really love The Princess Bride. It's funny, there's fantasy, there's romance... Also A Hitchhiker's Guide to the Galaxy and Pride and Prejudice. Please note I'm not listing anything particularly uplifting, just books that have made me smile and/or feel lighthearted. They're not heavy, basically.
As for movies, go with Teddy's classics list, we watch a lot of awesome movies from before the cataclysm.