Kanye West is not only our most optimistic guess for the June 30th slot, but it is also the most realistic. West is playing a small number of festivals throughout the country (Governor’s Ball) this summer and he is even going on a huge tour later in the year (dates TBD). Of course too Kanye has a new album to perform and promote with The Life of Pablo. Don’t forget, Kanye has also played Summerfest before in 2011, and it was a more than memorable performance. This would not only be a great choice for a Summerfest headliner but it is also our favorite.