Possible Clues:

• Older sibling who keeps an unwelcome eye on you?
• Important monk, one exercising oppressive control
• Orwellian overseer
• 1984's totalitarian controller — TV reality show
• Autocratic leader runs into considerable trouble
• Personification of a totalitarian state
• Dark presence in '1984'
• Relatively important dictator?
• A show of reducing captive population's surveillance?
• CBS reality show