The Truman Show (1998)

Peter Weir's film, from Andrew Niccol's script, imagines an insurance salesman whose entire life is a television show he does not know he is starring in. In 1998 it played as satire pushed to an absurd extreme; two decades of reality television have since made it look almost restrained. Jim Carrey, then best known for rubber-faced comedy, won a Golden Globe for playing Truman straight, and Ed Harris won one too. The town is the real planned community of Seaside, Florida, whose pastel perfection does half the unsettling work. It is the gentlest film on this list and the best place to start for anyone unsure about the darker titles.