Stolen: Michelangelo Merisi da Caravaggio, "Nativity with St. Francis and St. Lawrence (The Adoration)"
Location: Palermo, Italy
Year: October 1969
Worth: $20 Million

What grants this heist a spot on our list is the endless list of rumors that speculate on this valuable painting's whereabouts. The local Sicilian Mafia are prime suspects, given that a former gangster admitted to stealing it after receiving orders from someone with higher rank. There is an additional story of amateurs robbing the painting and subsequently selling it to mobsters. A third story is that the painting ended up tucked away in a barn where rats and pigs went at it, destroying it for all time. Other rumors say the painting was destroyed by earthquake or fire, while others think it still sits in a private collection. It's worth a lot, so if you ever see it cash in.