A Date With History

By Scott Smith in Arts & Entertainment on Nov 17, 2005 5:01PM

Everyone knows how important it is to have a mentor. Even the most savvy and successful individuals needed a leg up at some point. This week we learned that even the mighty Queen of Everything once got some help from a guy in the balcony.

Last Monday, Oprah Winfrey told her audience that none other than Roger Ebert convinced her to take her show into the lucrative world of syndication. This occurred while the two were out on a date.

We’ll give you a second to process that one. Roger Ebert and Oprah: on a date.

Ebert is a gentleman so he doesn’t kiss and tell. But he does relate the details of the conversation that convinced Oprah to take her show national. Apparently, Ebert grabbed a napkin and wrote out a chart that detailed how much money Oprah stood to make. After counting the zeros, Oprah exclaimed “I’m going with King World.”

Though Ebert jokes that he doesn’t get enough credit for advising that Jerry Springer NOT go into syndication, he fails to mention that he—as well as his ancestors—were the prime movers in the lives of other Chicagoans thanks to brief encounters over meals, drinks and hastily scrawled notes. For instance:

* Over cigars and cognac with Daniel Burnham, Hieronymus Ebert—Roger’s great-great grandfather—inadvertently inspires Chicago’s famous grid system of streets after drawing a tic-tac-toe game on a cocktail napkin.

* During the late 1940s, Nelson Algren is telling his agent, Reginald Ebert, about a book he wants to write on the city of Chicago with the working title of City On The Lake. Though known in the field as a shrewd dealmaker, Reginald was also a lousy typist and mistakenly wrote up a contract for a book titled City On The Make.

* After a movie premiere, actor Vince Vaughn confesses to Ebert that true happiness eludes him as he has no one to share his life with. Ebert offhandedly says “You know, that Jennifer Aniston is a nice girl. You should call her.” Though initially unconvinced, Vaughn is later swayed thanks to a drawing of Aniston on the back of his premiere pass (a not-to-scale reproduction is at right).