Ranked in order by creepiness. I'm still scared of 1/2 of these.
The Evil Typerwriter
Episode: "The Tale Of The Dream Machine"
Why it was scary: The typewriter made everything you typed on it come true. This is the only object on the list. No one uses typewriters anymore, so this one isn't as scary. That's why it's #50.
Sardo
Episode: Too many.
Why he was so scary: Sardo wasn't actually very scary, he was more of a little bitch. He always started drama.
The Sandman
Episode: "The Tale Of The Sandman"
Why he was so scary: The Sandman was played by Bobcat Goldthwait. His voice is basically made of nightmares.
Roy
Episode: "The Tale of Station 109.1"
Why he was scary: Gilbert Gotfried's voice is also made of nightmares.