The Rapper: Kid Cudi
Where He Cried: On Twitter in December 2011
Why He Did It: Okay, so we didn't actually see Cudi cry. But, after one of his biggest fans Ben Breedlove died shortly after uploading a series of videos that showcased how much he loved Cudi, the Ohio rapper got on Twitter and shared a message of his own. "I am so sad about Ben Breedlove," he said. "I watched the video he left for the world to see," he tweeted. "I broke down, I am to tears because I hate how life is so unfair."