Depends on whether I’m a suspect or not. If I am, just the one would do it. If I’d have to stand nearby and listen to a conversation between more than one of them, then I believe two would send me over the edge.
How many Gollums would it take to get you scared enough to slip on your ring?
GIGObuster, I don’t usually use Internet-speak, but with that comment YOMANK.

My preciousss? One Gollum would be enough, if he could sense the ring.
How many hobbitses would it take?
I’m pretty sure I could take up to three hobbitses without worry, unless they’re carrying weapons. Just one if he has a sword. And the seventh meal of the day hasn’t been served yet.
How many hyperkinetic rabbity things would it take?
Having just gone thru my entire videotaped collection of Sam & Max, freelance police, Fox Kids edition, I can safely say that ONE of him is more than enough?
How many cute little hydrocephalic kittens would it take?
Just one cute little hydrocephalic kitten would scare me; I’d never know what was going through its oversized little head.
How many CMOT Dibblers would it take?
I’d say that just one would be annoying enough.
How many claiments to various royal titles would it take?
Just one claiment to various royal titles would do it, assuming the bastard was serious about it. We got rid of stupid royal types over two centuries ago and don’t plan to start again now!
How many Agent Smiths would it take to get you to wet your pants?
Hmm… depends if I’m Neo or not. I’m pretty good at video games, but I’ve never been jacked into one. Don’t know what my brain would be able to accomplish. But assuming I’m not, if it’s Matrix 1 Agent Smith, he’d need 5 or 6 to scare me. If it’s Agent Smith from the sequels, his absorbing people power makes even one scary.
How many Isz (from The Maxx) would be scary?
Hey! A Max fan!
It depends: It is a white Isz or a black Isz?
If it is white: about 1000.
If it is back: one is enough.
How many Batmans?
Sorry: that was supposed to be “The Maxx”!
Still surprised why Batman did not appear until now.
Well are the Batmans prepared or not? I’d say five of the new look Batmen, or one of the old TV series Batman, would be enough to make me hide under the bed.
How many Muppets would it take to leave you a quivvering wreck?
You could stuff the room entirely full of muppets and I’d still not be worried. Unless you had Animal in there.
How many Phantoms of the Opera would it take to make you cry for your mommy?
[aside]Anyone else notice that elfkin477 started this game and then promptly scarpered off? You don’t suppose we scared him off, do you?[/aside]
It depends on what version. I could deal with a dozen Michael Crawfords, but only 2 Lon Chaneys.
How many polo players (with horses) would it take before you started to panic?
(polo players are characters?)
I’d say it’s the horses that are the main problem. In a 10x10’ room, two horses are a serious hazard.
How many Marios would freak you out?
Just one’s not too bad, but both Mario Brothers together would indeed be frightening.
How many damn, dirty apes would it take to leave you speechless?
One with a gun. Or General Ursus, alone.
I see that I repeated hobbits, my apologies… Let’s try a different direction. How many Ferengi would instill fear in you?
Just one. More than that and they’ll be too busy scheming against each other to worry about some puny hu-man.
How many copies of Geddy Lee would send you packing?
One, since I don’t like Rush, but Rush fans probably won’t start caring until the room fills up.
How many Horatio Hornblowers will it take before you move to a state without a coastline?
[sub] I’m over here crying because you think I’m a boy [/sub] 