Pennywise the Clown | Stephen King’s IT! (1990)
To really get a sense of how terrifying Pennywise is, you should read Stephen King’s novel, It. Well, that’s a guess since we never read it. But Tim Curry’s portrayal of the murderous clown/giant spider (yeah that one took us by surprise, too) gave us the chills despite the movie being five stars on the Shit Meter.
However, we have hope for the remake: