Since I'm sure you've already heard a lot about more mainstream stuff, I'll suggest stuff more off the beaten path.

Movies

City of God
Trainspotting
Amelie
Run Lola Run
The Lookout
The King of Kong

Books

Extremely Loud and Incredibly Close
Life of Pi
A Clockwork Orange
Survivor: A Novel
The Amazing Adventures of Kavalier & Clay
Most of the work of David Sedaris
Hello, Lied the Agent, and Other Bull You Hear As a Hollywood TV Writer

Comics

Watchmen
Invincible
Scott Pilgrim
Runaways
Y: The Last Man (especially now that it's complete)


My TV Show suggestions are the same as everyone else would recommend: Scrubs, House, Weeds, Entourage, etc.

For music, there's way too much to recommend without looking for something in particular. I will say the most recent artist to blow my mind is DJ Mike Relm.