The Rapper: Kanye West
Where He Cried: On Jay Leno's primetime show in September 2009
Why He Did It: A couple weeks after he interrupted Taylor Swift's acceptance speech at the 2009 MTV Video Music Awards, 'Ye sat down with Leno to apologize to Swift, to explain his actions, and to talk about the passing of his mother. "Obviously, I deal with hurt," he said, before shedding a few tears, "and so many celebrities, they never take the time off. I've never taken the time off to really [grieve]."