Appreciation: Madonna

Madonna is cool because she does what she wants and she's usually successful. She's an artist who is totally in-charge of all aspects of her career, from her albums, to her videos, to her hairstyles and live concerts, and to her extremely calculated career moves (favorite: wearing a cowgirl outfit on the cover of a very Euro techno album, possibly to not alienate her middle American fans). She has pushed the boundaries of pop music so many times, and there's really no one else around who could write sturdy pop songs like her.