Weird History Food is going to get sloppy with this one talking about the history of the Sloppy Joe. Whether it came from Sioux City, Iowa, Key West, Florida or Havana, Cuba, the Sloppy Joe has left a deliciously large greasy imprint on the hearts of America. This loose-meat sandwich has been associated with school lunches, manly meals, and cheap, but delicious comfort food since the 1930s.