Never saw the show, but I have also wondered the same thing. And my guess? No. No one has any idea why the statement "Big Brother is Watching" is hilarious.

Just like when people say, "O, brave new world -- with such people in it!" My response is usually, "I loved that book!" And I get looked at like I am a jerkass.

Lmao that's a really good question! 1984 is my favorite book and I don't think I could watch Big Brother without feeling a little creepy about it.  

I bet whatever dipshit suit came up with the title didn't know.  Obviously he could correlate the term with being watched but I'd be willing to bet he never read it.

that bothers the hell outta me.