Jack Sparrow
In the early 2000s, Depp signed on to play Captain Jack Sparrow in Gore Verbinski and Jerry Bruckheimer’s “Pirates of the Caribbean.” An adaptation loosely based on a famous Disneyland ride, Walt Disney CEO Michael Eisner was terrified of the project and tried to shut it down, but was temporarily persuaded that with a bankable star like Depp involved, the movie should be a hit. This, however, didn’t last long.