Complex sentence: Gary is a "city" duck who used to be addicted to quack, a fictional drug which gave him problems with the puppet maffia, and also once portrayed a plastic surgeon who was specialized in making "ducked up" lips.
Split into simpler sentences: Gary is a "city" duck who used to be addicted to quack, a fictional drug which gave him problems with the puppet maffia. One time he's also portrayed a plastic surgeon who was specialized in making "ducked up" lips.