The granddaddy of all TV shows that leave you scratching your head (ala Twin Peaks and Lost) was The Prisoner.
Patrick McGoohan (above, who also co-created the series) played Number 6 - a former government agent (possibly the agent he played in Danger Man) who, soon after resigning, wakes up in "the village" - a quaint little resort in the middle of nowhere.
It's called The Prisoner, because Number 6 is not allowed to leave. And "the village" seemed to be one big conspiracy just to mess with his head. Confidantes turned enemy, enemies disappeared.
The original Prisoner ran in America on CBS for seventeen episodes in the late '60s. The series finale ("Fall Out") - in which Number 6 finally discovers the identity of Number 1 - has divided fans of the series for decades.
It was pretty wild stuff at the time. Check out this clip - and try to imagine it co-existing on the same network as Gomer Pyle and Mayberry RFD.
AMC has a new Prisoner series starting next week (11-15) starring Jim Caviezel and Ian McKellan. I believe IFC is currently showing the original classic episodes - however, Blu-Ray aficionados might want to get the newly re-mastered complete series in High Definition.
