Oprah Winfrey and Roger Ebert

In a peculiar celebrity pairing from the '80s, media mogul Oprah Winfrey and renowned film critic Roger Ebert shared a unique connection. In 1983, Oprah Winfrey embarked on her journey as the host of a low-rated thirty-minute morning talk show in Chicago. Astonishingly, under her influence, the show's ratings skyrocketed from last place to first. During this transformative period, film critic Roger Ebert played a pivotal role by persuading Winfrey to sign a syndication deal, confidently predicting that she would amass an extraordinary fortune.

Ebert's prediction proved accurate as Oprah Winfrey became a media powerhouse, extending her influence beyond television. During this time, the two shared more than professional ties; they were romantically involved. However, as fate would have it, Roger Ebert married trial attorney Charlie "Chaz" Hammersmith in 1992, marking a significant turn in his personal life.

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