First: Who would win in a fight between Captain Jack Sparrow and Captain Jack Harkness? At times in their life when neither of them are immortal.

Second: Who would win in an insult swordfight between Guybrush Threepwood and Elan from Order of the the Stick?

That second one would be really funny, actually.

Elan: Looks like you've brought a dagger to a swordfight. Which I'm sure Elaine has said to you in the bedroom more than once.
Guybrush: How appropriate. You fight like a cow.
Elan: You might be familiar with our family recipe for shish kebabs!
(Stabs through the chest)
Guybrush: First you'd better stop waving your sword around like a feather duster.

Well, it'd be funny if someone other than me did it.