Clojure - 160 154 Characters
(#(if(= % "BYE")%(do(if(=(.toUpperCase %)%)(prn(str"No, not since "(+ 1930(rand-int 9))"!"))(prn"Huh?! Speak up, sonny!"))(recur(read-line))))(read-line))
Working on golfing it a bit more. Suggestions welcome.
Run through REPL