Charlie Chaplin already had more than 100 silent movies under his belt when, in 1938, he decided to take on the role of Adolf Hitler. When The Great Dictator came out two years later, it was the first time Chaplin spoke on film.

In the The Great Dictator, Chaplin played his trademark Tramp character, re-imagined as a Jewish barber in the fictional country Tomania. Chaplin also played Tomania’s autocrat Adenoid Hynkel, a parody of Hitler.

In 1939 and 1940, Nazi Germany captured much of Europe and began bombing Great Britain. But America was not formally at war. And many Hollywood executives were reluctant to criticize Hitler.

Some Jewish film producers in the U.S. feared a parody film might anger the Nazis and expose Jews in Europe to even harsher treatment.

Others were sympathetic to the Nazis. In the 1930s, MGM’s Louis B. Meyer had consulted with German authorities and had given them veto power over some films’ contents in order to ensure easy access to the German film market.

“Hitler can’t get any worse than he is now,” Chaplin told executives. The 51-year-old Chaplin, then one of the world’s greatest celebrities, decided to produce The Great Dictator with his own money. He wrote, directed and starred in the film.

But Chaplin himself almost nixed The Great Dictator as the extent of German atrocities in Europe became clearer. The film star feared there was simply nothing funny about Nazis. He also worried that many countries might simply ban the flick.

President Franklin Roosevelt heard of Chaplin’s intention to scrap the film. The president sent an aide to deliver a message to Chaplin. “Make this film,” the president advised. Roosevelt promised he would use his influence to ensure none of America’s allies banned the movie.

Filming began in 1939 and lasted more than a year. Chaplin released the movie in October 1940. Hitler demanded a copy—and screened it in his private theater twice.

Hitler once had extolled Chaplin as one of the greatest performers of all time. There were rumors that Hitler was heartbroken to see Chaplin’s impersonation of him. In one key scene, Chaplin’s Hynkel character bursts into tears after his balloon globe pops.

But according to a member of Hitler’s circle named Reinhard Spitzy, the real-life Nazi leader found the film amusing. Spitzy even suggested that Chaplin had inspired Hitler’s toothbrush mustache. The other explanation for the Führer’s ’stache is that Hitler shaved it that way when he was a soldier in World War I in order to get a good seal on his gas mask.

Hitler screened Chaplin’s films even though Germany had banned the actor’s works owing to his alleged Jewishness. The propaganda book The Jews Are Watching You had labelled Chaplin a “disgusting Jew acrobat.”

The Great Dictator was a commercial success. Later, Chaplin regretted it being so funny. He insisted that had he known about the Nazi’s industrialized murder of the Jews, he “wouldn’t have made the film.”

As written, the original ending of The Great Dictator included an elaborate dance sequence. At the last minute before filming, Chaplin wrote a monologue instead—the first words he would ever speak on film. The Tramp delivers the monologue after secretly assuming Hynkel’s identity and reversing the dictator’s racist policies.

“I should like to help everyone if possible—Jew, Gentile, black man, white,” Chaplain said as the Tramp. “We all want to help one another. Human beings are like that. We want to live by each other’s happiness, not by each other’s misery. We don’t want to hate and despise one another.”

“Greed has poisoned men’s souls, has barricaded the world with hate and has goose-stepped us into misery and bloodshed,” he continued. “We have developed speed, but we have shut ourselves in. Machinery that gives abundance has left us in want. Our knowledge has made us cynical. Our cleverness, hard and unkind.”

“We think too much and feel too little. More than machinery, we need humanity. More than cleverness, we need kindness and gentleness. Without these qualities, life will be violent and all will be lost.”

After the war, someone asked Chaplin if he was in fact Jewish. “I’m afraid I don’t have that honor,” Chaplin said.

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