Music, Film, Journalism, anything involving chaos, disorder, revolt, "especially things that seem to have no meaning." Purpose, the cosmos.
Jesus and Albert Einstein... Too perfect
The Life Aquatic with Steve Zissou, Chinatown, Fear and Loathing in Las Vegas, Star Wars, etc.
Family Guy, Seinfeld, The Simpsons, Home Movies, Chappelle's Show, South Park.
Hunter S. Thompson and Tom Wolfe... George Orwell is interesting. Any books on philosophy or biographies on interesting people.