19. Kanye West
This was the worst. An entire swath of the population put their hopes in Kanye, for the return of artistry to music; the return of honesty to pop culture, of pure id to celebrity. He had built up an ever-expanding catalog of classic music, first injecting soul into hip-hop, then strings, then synths, then sobs.
And then he threw it all away on an empty bottle of Hennessey, after tottering on the hip of Amber Rose, because Taylor Swift had the gall to win an award that really-really-should've gone to Beyonce. It was so regrettable, but it was so Kanye. And he was so right in saying it. That's not the point of this list, but it had to be said. Anyway, it became this whole big thing; President Obama called Kanye a "jackass" and Kanye disappeared for a while.
There would be reports of him popping up in London or Paris, working on this or that; it was a dark time. And then "Power" dropped, an unapologetic asshole unleashed. This was Kanye the underdog, Kanye the villain. Where his climb to the top of hip-hop was quick, this gave him the brushback he needed; because of it, he's emerged stronger than ever. Good luck getting rid of him again.