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5. Leonardo DiCaprio. The Internet feels really bad today for #PoorLeo. Leonardo DiCaprio has now been nominated for an Oscar four times as an actor (and once as a producer on Wolf of Wall Street) and he has lost every single time. Since success in Hollywood is measured in statuettes, DiCaprio might as well be a commoner. Look, Leo. It doesn't take a genius to figure out what you need to do to win. Get cast as the lead in some heartwrenching film about a president/athlete/devastating virus. Go all method and lose at least 35 pounds to prepare for the role. Show up and collect your golden statue. Done and done.