5. The King of Comedy
The darkest film that Scorsese has ever made. While he may have made an outright dark comedy with After Hours his most morbidly hilarious movie is The King of Comedy. Robert De Niro plays a character, named Rupert Pupkin, who appears likeable and normal on the outside but is secretly a psychopath who harbors traumas that have shaped him into a disturbed individual who doesn't even know how to follow the most basic rules of society. He is constantly trying to get his hero, Jerry Langford, to hear his act and spread it to the world. Scorsese uses this to present the darkest and most ironic scene in his entire career. When Rupert finally gets to share his act with the world not only is his comedy creepy but it's not funny at all. For a film called The King of Comedy this was a brilliant move that makes the movie one of the best black comedies ever made.