The more depressing the better, but genre doesn't really matter much . . . The Weepies, Tim Christensen, Damien Rice, Duncan Sheik, Infected Mushroom, Garth Brooks, Tim McGraw, Shinedown, Metallica (the old stuff), Velvet Revolver, Boston, The Album Leaf, Billy Joel, The Eagles, Elton John, Erlend Oye, Evanescence, Fiona Apple, Hootie & the Blowfish, Glen Phillips, Nickel Creek. . . and so forth
Anything from Wes Anderson, Lock Stock and Two Smoking Barrels, Snatch,L4yer Cake, Swingers, Road Trip, Office Space, Nothing to Lose, American History X, LA Confidential, Traffic, Anything from Baz Lurhmann, anything with Vampires, Dead Poets Society, Harry Potter (especially 3)
Deadwood, Farscape, Arrested Development, SF Giants Games, How I Met Your Mother, Lost, Rome, Scrubs
George RR Martin, Jacqueline Carey, Roger Zelazny, Magaret Weis & Tracy Hickman, Robert Ludlum, Stephen King, Frank Herbert, Anne Rice, RA Salvatore, Tolkein, CS Lewis, Shakespeare, Harry Potter, Margaret Atwood, Terry Pratchett, Hemingway, Faulkner, (i'm kinda into reading by the way), Tom Clancy, Bernard Cornwell, Daniel Silva