Music:
Wilco, Widespread Panic, Phish, Ryan Adams, Golden Smog, M. Wade, John Prine, Black Crowes, Galactic, Yonder Mountain, John Coltrane, Thelonius Monk, Miles Davis, Bob Dylan, Grateful Dead, Jon Scofield, James Brown, St. Germain, Massive Attack, DJ Shadow and a whole lot more alt country, jazz, bluegrass, jambase, folk, blues, and electronica...
Movies:
Pi, Usual Suspects, Layer Cake, Requiem for a Dream, Natural Born Killers, Friday, American History X, War Documentaries...
Television:
Weeds, Entourage
Books:
DaVinci Code, Angels & Demons, Freakonomics, Krakauer, Kerouac (somewhat), Hemingway, Classics & History mostly
Heroes:
Kerouac, Hemingway, Steinbeck, Bob Dylan, Rosa Parks, Abe Lincoln, FDR, and anybody who can live a financially unconcerned life floating around, drinking and writing in a temperate climate