The "man" is someone or something that holds you down or supresses you. Damn The Man is basically a way of saying screwwhatever's holding you back and going for it.
The best work of literature ever. The author chose his words carefully to create such a masterpiece. Words like "Turts" "Turty" and, of course, "Perchance" only help the writer prove his point.
Person 1: "Have you read 'Mario, the Idea vs Mario, the Man' yet?"
Person 2: "What is that"