Benito Mussolini

Benito Mussolini (July 29, 1883 – April 28, 1945) was Fascist Duce and Prime Minister of Italy and from 1921 to 1943. He allied Italy with Nazi Germany and Imperial Japan during World War II. When Italy surrendered and joined the Allies in 1943, Mussolini fled North and was made head of an Italian puppet state controlled by Nazi Germany. Near the end of the war, Mussolini was captured by partisans when trying to flee to Germany with his mistress. They were executed, and Mussolini's corpse was taken to Milan, where it was hung upside down in a public display with other members of his regime.

 References 
 * Mussolini appears seated with Adolf Hitler and German Air Marshal Hermann Goering in a flashback in the episode "Whacking Day."
 * In the episode "The Italian Bob", Homer makes gestures remeniscent of Mussolini when presented to an Italian village.  When Lisa calls him  out on this, he says that he thought he was imitating Donald Trump.

 Trivia
 * Milhouse's maternal grandmother, Nana Sophie, shares the surname "Mussolini."