Movies:
Wedding Crashers, Old Skool (Actually anything with Vince Vaughn - hubba, hubba), Boiler Room, Three Kings, Matchstick Men, Fight Club, Crash -- I think Crash should be a mandatory must see for all highschool students.
Television:
Arrested Development, The Office,
Curb Your Enthusiasm, Lost, Martha Stewart
-- I was terribly sad to see Six Feet Under end
Books:
Love
in the Time of Cholera (Gabriel Garcia Marquez)
Don't
Let the Pigeon Drive the Bus (Mo Willems)
I
am Too Absolutely Small for School (Lauren Childs)