There are several different legends surrounding the origins of this symbol, but the themes of love, tragedy, and betrayal are central to all versions. A popular yet macabre version tells of a beautiful woman from Palermo who fell in love with a Moorish man; sometimes, he is a merchant, other times a soldier, but all stories agree that he eventually tells her that he has to return to his homeland. He confesses that he already has a wife and children there, and he must return to them. Blinded by jealousy and sorrow, the woman beheaded her lover and used his head as a pot for her basil plant. The basil plant grew fast and full, attracting the attention of her neighbors, who crafted similar (albeit ceramic) vases for their plants.
Another version comes from Boccaccio's Decameron and tells the story of Lisabetta, a young noble girl from Messina who falls in love with a young boy from Pisa without noble origins. Upon discovering the affair, her brothers kill the young boy and bury him. Lisabetta finds the spot where he is buried and digs him up. Unable to give him a proper burial, she decides to remove his head and take it with her. She buries it in a pot and plants basil overtop. The tears she cried onto the plant are said to have helped it grow fast and strong.