TV: The Prisoner
Patrick McGoohan passed away recently, but his most celebrated work continues to live on - "The Prisoner":
The premise is delightfully surreal - a British agent (played by Patrick McGoohan) resigns, and suddenly finds himself inside a prison called "The Village." The mysterious people controlling the Village are after information, and their struggle to unearth it from McGoohan's character (whom they dub "Number Six") becomes a deadly test of wills. While at first the Village administrators try simple ruses and psychological tricks, they eventually resort to more extreme methods (like mind-altering drugs). The whole thing plays out like a dream, which gives "The Prisoner" a timeless quality.
I became acquainted with "The Prisoner" through my public library. It had some grainy old VHS tapes of the series, and I watched them enthusiastically in my youth. The library didn't have the conclusion of the series ("Fall Out") so for the longest time, I didn't know how it all ended. Not that seeing the last episode solves anything - the ending is almost as cryptic as the rest of the series.
Perhaps the most famous aspect of "The Prisoner" is Rover, the semi-autonomous sentry that invariably blocks Number Six's escape attempts. Imagine being in a quaint little seaside town but being unable to leave, since every escape avenue is cut off by a giant white weather ballon. It's the stuff of nightmares, certainly.