Roger Ebert and Oprah

For 20 years, film critic Roger Ebert has kept his lips sealed about his relationship with Oprah…until today! On Oprah's 20th anniversary special she revealed—for the first time—that Roger was the person who convinced her to go into syndicataion…while they were on a date!

Roger says since that show, his "'cred' has gone way up!" In his Chicago Sun-Times column, Roger says that he and Oprah went on not one, but two dates back in the '80s.

For their second date, Roger says they went to see the Count Basie Orchestra. But, he recalls, Oprah had to leave early so she could get up at 5 a.m. to host her new talk show.
Roger Ebert and Oprah

Oprah may remember her first date with Roger more clearly because it's the one that really paid off!

Naturally, Roger took Oprah to a movie on their first date, and then he treated her to dinner at the Hamburger Hamlet. Over dinner, Oprah told Roger that both King World and the ABC stations wanted to syndicate her local talk show, but she wasn't sure what to do.

Roger grabbed a Hamburger Hamlet napkin and started jotting down some numbers. First, he took his annual salary multiplied by two (because his co-critic at the time, Gene Siskel, made the same salary). Then, he multiplied that number by five since Oprah's show would be on five days a week. Finally, he doubled that number to reflect the hour timeframe, and then doubled it one last time because he was sure her show would be a huge hit!

He slid the napkin across the table to show Oprah the final tally and she said, "Deal done!"