12. Roger Ebert Once Dated Oprah Winfrey
Roger Ebert is also a Pulitzer Prize Winning writer. And they don’t hand these out to just anybody. In 1975, he was awarded the Pulitzer Prize for Criticism for his writing. Gene Siskel, on the other hand, was a Yale graduate with a degree in philosophy. Even though the pair is considered as acclaimed thinkers, they were commendeded for not talking down to their audience and for appearing more like quarreling brothers than university professors.