Last April or May or so I saw Chip Kidd speak at USC. It was the first time that I had ever been up close and personal to a well known artist that I admired (and still do). His work to me is amazing because of all of the elements it has to incorporate in order for the book cover to be successful. His range of abilities cover almost every style, and each cover has a uniqueness that most covers don't have.
Most of his work is humorous and tongue in cheek- take a look at his own book- he photographed his hands holding a miniature portfolio of his work. His website has the layout that graphic designers (especially book designers) are all too familiar with (to ad nauseum).
He works freelance, doing about 75 covers per year and is in high demand. He went to Penn state and according to him he just 'fell' into the world of book design. He got a low level job and found that he had a knack for it and it became his career.
