Music:
Dave Matthews Band, Ryan Adams, Phish, the Roots, Bowie, Springsteen, Beatles, Allman's, Johnny & Willie, Lyle Lovett is pretty cool too, Jimmy Buffett, Tribe Called Quest, LL, Run DMC and Public Enemy (takes me back to road games in HS & college).
Movies:
The list is long...Animal House, Goodfellas, Godfather I & II (not III), Caddyshack, Blazing Saddles, Top Gun, Tombstone, Nutty Professor, Meet the Parents, anything where Jay and Silent Bob make an appearance, Good Will Hunting, Easy Rider, Billy Madison, Happy Gilmore, Major League, Apocalypse Now, Heat, Carlito's Way, Seven, Silence of the Lambs, Old School. There are more but I just can't think of em all.
Books:
The Art of Happiness (drank the cool-aid and picked up a Dali Lama book), anything by Ambrose, McCulloch (historical biography)