5. Sheldon Cooper (The Big Bang Theory) & Dewey Wilkerson (Malcolm In The Middle)
The reason I think these two should meet is because I can imagine it being hilariously uncomfortable for Sheldon. Sheldon is very intelligent and extremely socially awkward, while Dewey will talk to anyone, is also extremely intelligent (though he often hides it) and is also very, very crafty. However, both are very quirky and massively detached from reality (or at least what others consider 'reality' to be ). Sheldon is famed for his 'BAZINGA!' practical jokes, but I can't help thinking that he would be the one on the end of those jokes if he met Dewey - and that would be extremely funny to see. Dewey has the ability to outwit Sheldon, due to Sheldon's naivety and Dewey's ability to appear less intelligent than he really is. I can also see them having quite a lot to talk about as they have several things in common - a very high intellect, a less than stellar relationship with their families, early childhood memories that have had a prolonged effect on their lives, the aforementioned detachment from reality, typical childlike qualities (despite the fact that one of the two is a fully grown adult) such as stubbornness and a craving for attention and an ability to be supportive when the situation really requires it.