Ever watch a TV show and know that the main character said something really deep? Or read a book and understand that the main focus of the story has large moral implications? But you can't quite put into words what you are thinking and feeling; you don't have the educational background to put this into context with larger philosophical themes. Consider the Blackwell Philosophy and Pop Culture book series.
Each book takes on a work of pop culture and provides essays written by professional philosophers (usually professors or associate professor of philosophy in a university) examining a certain aspect of the comic book, TV series, movie or other pop culture artifact. Of interest to me were the two books, Watchmen and Philosophy and Battlestar Galactica and Philosophy, but with over 100 books just about every genre and media is covered. There is Futurama and Philosophy, Baseball and Philosophy, Hitchcock and Philosophy, Harley-Davidson and Philosophy (full throttle Aristotle), Metallica and Philosophy, etc. The essays always refer to other philosophical works by influential philosophers, so if you would like to go deeper in a particular type of thought, this gives you a relevant starting place.