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This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.
Halloween Horror Nights
The Usher and the Director are best friends.
They both have a huge interest for cinema, and they are both really scary to meet (the Director moreso).

H.R. Bloodengutz is the Caretaker's minion.
Or is he the Caretaker?

The Caretaker's wife died.
Might seem possible. He and his daughter Cindy are the only Caine family members known to still be alive.
  • It would also explain his obsession with studying the soul, at least initially. He wanted there to be proof of the soul, and therefore the afterlife, so he'd know what happened to his wife. Unfortunately, things went downhill fast...

The Director is the Storyteller's son.
Seeing as how they have similar Creepy Blue Eyes in appearance.

Honey O'Houlihan is Lady Luck's alternate personality.
If Lady Luck were in disguise as Honey O'Houlihan, this might mean that Lady Luck and Dan would possibly become a couple. Dan told Honey that he likes women who kill people. Not to mention Dan and Lady Luck both have Green Eyes.

Eddie and Cindy will eventually become icons of future events.
Not sure if that would happen though.
  • Cindy was originally intended to be the icon for 2010 before they decided on Fear, so at the least, it shows that past icons are still in the running.

The Caretaker is Amos Howell.
They are both evil, and very similar in appearance.

Lady Luck is an enemy of Buffy Summers.
Lady Luck's monster form resembles the vampires in that show heavily judging by the face.

Universal Studios plans on making films based off the Halloween Horror Nights icons.
That would be really cool. One about the Caretaker would be awesome.

The Director is related to the Imposter Dan somehow.
They are close to looking the same. The differences are that the Imposter Dan has a different hairstyle, a goatee, a different-looking nose, and is much friendlier. The Director on the other hand, has an extremely psychopathic personality, and actually does have an evil plan.

Jack the Clown's rival is Ronald McDonald.
Jack insulted Ronald on a radio interview during 2007, telling him to "eat that".
LEGO Dino AttackWMG/Other    

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