Time and time again, the world’s most successful fashion models attempt to dip their toes in the thespian pool. Maybe it’s to prove their talent goes beyond beauty? Maybe they think age has led their looks to no longer be relevant? Or maybe modeling was just a side step on their way to winning multiple silver screen awards? Whatever the case may be, attempts at acting accolades can be a dicey maneuver for all parties involved. As Kate Upton takes on her first official starring role in The Other Woman, The Daily Beast ranks our favorite models-turned-actresses from best to worst—starting with Cybill Shepherd's rise to Hollywood fame, all the way down to Naomi Campbell's seriously disasterous cameos.