The origin of this meaning was used first at a Harkins Theatre, when a customer asked for, instead of a small, a tall drink (such as the smallest size at coffee shops). Ever since, it has been used to describe how incredible something is.
Barista: Oh, you wanted a "Short". You didn't say "Short". Do you want a "Short" then, hmmmmm?
Customer: Well...uhhh...yeah...of course.
Barista: Well you should've just said so in the 1st place.
Customer(seething): You just lost your tip.