Hollywood careers are built on smart (and not always obvious) choices. The two men who top our list of Hollywood’s highest-earning actors are living proof of that. While Johnny Depp topped our list last year with $75 million, Leonardo DiCaprio jumps from fifth to first place to beat Depp for the first time. Over the past year Depp earned $50 million to DiCaprio’s $77 million. Both actors have achieved wealth and fame by making some unusual choices with their careers.