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Oprah Winfrey had an unlikely advisor when she first considered going national with her talk show, The Oprah Winfrey Show. Film critic Roger Ebert was the first to encourage the media mogul to pursue syndication. The two were on a date when the topic came up, and the conversation they had changed the world of daytime talk shows forever.

Winfrey revealed on the 20th anniversary episode of her show that it had been Ebert who pushed her towards syndication. Ebert, who hadn't shared that information with anyone, wrote about the experience on his website. "All of these years I have maintained a discreet silence about my role as Oprah's adviser, but now that she has spilled the beans, the time is right to tell the whole story," he wrote.

The late movie reviewer started from the very first time he met the soon-to-be star, back when she was hosting a morning talk show based in Baltimore. The actual show was a pitfall of disasters. Her guests that day included Gene Siskel and Ebert, a vegetarian chef, and a group of four little people dressed as chipmunks who could hula hoop while singing "The Chipmunk Christmas Song."

Oprah was always the professional

Almost immediately, the show went off the rails when the chef, in a blender incident gone wrong, accidentally sprayed zucchini puree all over the interview couch. Showing that even early on, Winfrey was a consummate professional, she nonchalantly flipped the couch cushions during the commercial break. That's when Ebert had a realization. "I realize during this show that Oprah Winfrey is a natural on television, although she could use a better booker," the critic wrote.

A few months later, Winfrey and Ebert were out on a date. They went to see a movie and later chatted over dinner at the Hamburger Hamlet. While there, Winfrey admitted to being at a crossroads in her career. She'd recently been hired to host AM Chicago, which took on ratings giant Phil Donahue and won. That caught the attention of not only the ABC station she was on, but King World Productions, which was acquired by CBS in 2000.

"I don't know what to do," Ebert recalled Winfrey telling him. "The ABC stations want to syndicate my show. So does King World. The problem with syndication is that if your show isn't successful, you're off the air in three months. The ABC stations own themselves, so they can keep you on. Which way do you think I should go?" Ebert grabbed a napkin and performed some quick math for Winfrey, outlining what she could possibly earn if she chose to sign on with King World. "I pushed the napkin across the table. Oprah studied it for 10 seconds. 'Rog, I'm going with King World,' she said." The rest was history.

Winfrey is a household name, so tabloids will sometimes exploit that in order to push false narratives. For instance, Woman's Day reported in 2018 that Winfrey was playing peacemaker for Meghan Markle and her father, Thomas. The father-daughter duo have been estranged since Meghan's wedding to Prince Harry. A rep for Winfrey exclusively told us there's "no truth" to the publications outrageous claims.

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