Movies:
They Live
Equilibrium
V For Vendetta
Dark City
The Manchurian Candidate
Nineteen Eighty-Four
The Good Shepherd
Eyes Wide Shut
Network
Wag The Dog
My Dinner with Andre
From Hell
The Men Who Stare at Goats
Fahrenheit 451
Pi
The Boys from Brazil
Eye opening movies.
In addition (and seconding) to the ones already mentioned:
1984 (1952) : if you're too bored to read the book
The Wicker Man (1973) : the atmosphere, the rituals, the hidden secrets
Conversation (1974) : paranoia at it's best
Parallax View (1974) : silly, but shows all the basic MOs of players
Three Days of the Condor (1975) : when you are alone, who do you turn to?
Capricorn One (1978): How fake moon landings were made into a conspiracy - it's like a meta-documentary
Blow Out (1981) : the feeling of paranoia
Edge of darkness - UK TV Series (1985): how corporate, military and governmental conspiracies mix together
House of Games (1987): how the con game is played
JFK (1991) : how corruption goes to the top - you can't win
Waco : the Rules of Engagement (1997) - how it's done in real time, in day-time television and everybody gets away free (only the innocent die)
The Spanish Prisoner (1997) : more about corporate conspiracies
They Live! (1998) : just for the street ads, the fight sequence and the bank sequence alone
The Insider (1999) : corporate corruption is daily biz
The Skulls (2000) : it's like a cheap and trashy ad for Skull & Bones
Syriana (2005) : how field agents are / get corrupted
Exomologisi enos oikonomikou dolofonou (2007) : Based on John Perkin's 'Confessions of an Economic Hitman'. If you haven't read the book, you should, 'cos this is the way the world works
One By One (2014) : conspiracy of depopulation - more like a docu
Turks & Caicos (2014): where old spies go to hang out and retire, but can't help being spies
Hog. House of Games. Great one.