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Let’s be real — Oprah Winfrey doesn’t need two names. The mogul is synonymous with success, having climbed the business and entertainment ladders for decades. As her 2020: Vision Tour continues, it’s worth exploring how the star got her start. One famous name claims credit, but is it true?

Oprah’s career spans over 30 years, but her love life is complicated

Oprah
Oprah Winfrey speaks during the WW (Weight Watchers Reimagined) & Oprah’s 2020 Vision: Your Life In Focus Tour | Jason Koerner/Getty Images

One can’t simply sum up Oprah’s career in a sentence, or even a paragraph. The star held the highest-rated talk show, The Oprah Winfrey Show. For 24 consecutive seasons, Oprah won every sweep since its 1986 debut.

The WW investor (formerly Weight Watchers) and business mogul hosted Baltimore’s “AM Chicago.” Eventually, she made her way into acting, writing, producing, and taking over the world.

While business was booming, Oprah’s romantic life hasn’t always met the same level of excellence. From her high school sweetheart, Anthony Otay, to the 1970 brief interlude with singer, John Tesh, Oprah’s maintained her professionalism and authenticity on-air and in real life.

Now, Lady O is with longtime boyfriend, Stedman Graham. They’ve been an item since 1986 with a 1992 engagement that never manifested into marriage. However, there’s one man Oprah dated that claims he’s the reason she became the Oprah we know today.

Which celebrity claims he gave Orpah her start?

Film critic, Roger Ebert, may have had a hand in launching Oprah into the masses. For 20 years, Ebert remained tight-lipped about his friendship with Oprah.

On her show’s 20th anniversary, Oprah announced he’s responsible for helping get her show into syndication — while they were on a date.

 “I was also the person who suggested that Jerry Springer not go into syndication, for which I have received too little credit,” Ebert wrote on his website blog.

“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 went into the detailed fever dream that put him and Oprah in fate’s hands. In the ’80s, the two first went to a movie, followed by dinner. Oprah revealed King World and ABC Stations expressed a desire to syndicate her talk show. But, she didn’t know what to do about it.

Ebert reportedly did the math on a napkin. He multiplied his salary by two (to reflect his co-critic Gene Siskel) by the number of days her talk show would be on (five). Then, he doubled it two times over, factoring in the time of day it’d air and his belief she’d be a success.

When he showed Oprah the number on the napkin, she didn’t hesitate.

“Deal done,” she said.

Ebert and Oprah went on one additional date to the orchestra, but Oprah left early due to her new talk show’s early start time. The relationship didn’t morph into anything more romantic, but the two stayed close over the years until Ebert’s passing.

Ebert passed in 2013 due to complications with thyroid cancer

With over 10,000 movie reviews under his belt, Ebert’s talent soared. The activist, screenwriter, historian, and inventor of “two thumbs up,” loved his career. His famous reviews (with Siskel) aired on a local program called “Coming Soon To A Theater Near You.”

The man had an eye for soon-to-be big things. Ebert invested in a small tech company now known as Google.

In 1992, the film critic married his wife of 18 years, Chaz, who stayed by his side as he underwent his battle with thyroid cancer. In an episode of The Oprah Winfrey Show, Chaz read some of Ebert’s journal writings on-air.

“I believe at the end of it all, if we have done something to make others a little happier and ourselves a little happier that is about the best we can do,” Chaz read. “To make others less happy is a crime, to make ourselves unhappy is where all crime starts.”

According to reports, Ebert’s diagnosis came in 2002. He had malignant tumors in his salivary glands in 2003 and reconstructive surgeries in 2006.

Those operations caused him to lose part of his jaw. He lost his ability to speak as many may remember and used a computer voice program to communicate.

The Pulitzer prize-winning writer died in 2013 from complications related to cancer. Oprah tweeted at the time, “Roger and Gene together again. End of an era.”

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