Artist: Rihanna, Alicia Keys
It was quite a transformation when Rihanna went from sunny Barbadian beach bum to all-black "Rude Boy" badass. During the promotions campaign for her album Rated R in late 2009 and 2010, she went from sun-soaked songstress to neo-rock rebel. As Rihanna transformed her image in something more formidable and slick, there was one person who worked closer with RiRi than anyone else on her team. That would be creative director Simon Henwood, who helped mold even the fashion-forward, badass brand of one of the world's biggest pop stars. Rihanna probably could never have made it over the crest of her Good Girl Gone Bad image without Henwood's strategy ,which helped her true brash attitude make the mainstream. His work with a slate of other pop stars, including Alicia Keys, positions him as a dominant creative force.