First is the book Word Freak: Heartbreak, Triumph, Genius, and Obsession in the World of Competitive Scrabble by Steven Fatsis. This book is an absolute hoot. It's the author's tale of his adventures attempting to become an expert-rated competitive Scrabble player, and the quirky Scrabble "professionals" he encounters.
Professional Scrabble, as you can imagine, isn't as lucrative as professional football or golf, and it attracts a really odd element who are willing to pursue it full-time. You'll meet folks like G.I. Joel, the Scrabble world-champion who appears to be proud of his chronic intestinal problems, There's also Matt, a part-time standup comic who was fired from the writing staff of SNL after a month, receives an allowance from his mom, and takes around 100 pills a day.
If you're a fan of Christopher Guest's movies Best of Show and Waiting for Guffman, which are centered around quirky characters and their odd backgrounds, then you should enjoy this book immensely. The characters in Word Freak are as odd as those in the movie, but they really exist.
Next is the movie The Dish. Your local Blockbuster should have a couple of copies tucked in the corner. This is an irresistible little true story about a radio telescope station in a sleepy Australian community that suddenly gets the world's attention when NASA recruits them to be the southern-hemisphere tracking station for the Apollo moon-landing. It's a fun, touching little movie, and it's not full of forced sentimentality like A.I. I don't recall a movie making me smile as much since October Sky.
I won't tell you about the scene where the local band plays the U.S. National Anthem, but I will tell you that it'll make you laugh out loud.