Celebrity Odd Couples: The Most Mismatched Hollywood Pairs Over The Years

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OPRAH WINFREY AND ROGER EBERT

Oprah Winfrey has been with her longtime beau Stedman Graham for over three decades. But before she set her sights on Graham, the talk show mogul went out on a few dates with fellow Chicagoan and budding film critic Roger Ebert. Even though the sparks didn’t fly, Ebert became Winfrey’s mentor. “Yes, it is true, I persuaded Oprah to become the most successful and famous woman in the world,” said Ebert.

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