Type of Media: Film
There's always a discussion around making jokes about horrible things. On the one hand people say those jokes help them cope with the darker things in life. Others argue that making light of a terrible thing belittles the suffering of those caught up in it, and doesn't really affect much change. Look at any tragic news story posted on Reddit. In the comments there will be at least one dark joke, followed by a wave of people saying "too soon".
In the 1930s, two of the most well-known men in the world were Adolf Hitler and Charlie Chaplin. It was a common bit for comedians to point out how the pair looked similar, mostly because they both wore a toothbrush mustache. When Chaplin heard about the Nazi's increasing repression of Jews from his European friends, he thought he could use this similarity and his comedic talents to satirize Hitler and the Nazi regime. Then he saw Triumph of the Will, the infamous Nazi propaganda film. He watched it again and again, studying Hitler's mannerisms and the cinematography closely. Chaplin knew how he could pull it off.
In The Great Dictator, Chaplin plays Adenoid Hynkel, Dictator of Tomania and the most obvious Hitler substitute ever put on film. The allegory between Tomania and Germany is so thin it almost doesn't exist, with Hynkel scapegoating Jews, putting them into ghettos, and harassing them with his militarized police, the Stormtroopers. Shots of rallies are ripped straight out of Triumph of the Will. Chaplin plays Hynkel as a short-tempered buffoon, constantly engaging in physical pratfalls and blowing up at his second-in-command, Herring. This ramps up even more when the dictator of neighboring fascist state Bacteria, Benzino Napaloni, comes to visit, as their incredibly fragile egos butt up against each other. Hynkel tries to make sure that Napaloni is physically lower than him at all times, resulting in a series of gags culminating in Hynkel and Napaloni seated in neighboring barber's chairs, furiously pumping their chairs higher so they can be the alpha male.
At the same time, Chaplin also plays a bumbling Jewish barber who looks and moves exactly like his beloved Little Tramp character. Suffering amnesia since the Great War and recently escaped from his mental hospital, the barber doesn't know who the Stormtroopers and Hynkel are. When he resists arrest simply because he has no clue of what's going on, the rest of the ghetto comes to see him as a hero who will fight back against repression. He and his neighbor Hannah talk about moving to neutral country Osterlich for safety, not knowing that Hynkel is planning an invasion. The plot of the movie alternates between laughing at Hynkel and laughing with the Jewish barber and Hannah, right up until the ending, where the barber is mistaken for Hynkel and asked to give a speech at a rally. The speech that follows has Chaplin looking directly at the camera and pleading for peace. All pretenses of him being in character effectively drop, as he decries dictators as greedy, unnatural men, and urges soldiers to think for themselves and stop following orders. Most relevant to today, he criticized technology advancing beyond human morality. He says if we can overcome these obstacles, humans can build a utopia. It's a speech that nearly got him branded a pinko.
As Chaplin was making The Great Dictator, he worried that people wouldn't want to see a comedy film about fascist dictators who, in real life, were doing very unfunny things. When it was released, however, the American public loved it and the Nazi-sympathizing world took it very seriously. While it was the second-most popular movie of the year in the US, The Great Dictator was banned throughout much of Europe and some South American countries. The UK, still practicing appeasement, announced they would ban the film before it was released in 1939, but once they joined the war they reversed their position and welcomed The Great Dictator to raise morale. The film didn't release in France until after the war ended in 1945, but when it did it became the most popular film of the year and absolutely destroyed the box office. The next highest-grossing movie didn't even make two-thirds of what The Great Dictator made.
While The Great Dictator probably didn't affect the outcome of WWII in any way, it clearly provided audiences some much-needed catharsis. It took a monster and turned him into a ridiculous stooge, not downplaying the harm he was doing, but equating his method with madness. It was the kind of act that, in the hands of a lesser comedian, would have gone over like a lead balloon.