If there was a defining moment in Oprah Winfrey's business career, it came in 1986, when King World offered her a syndication deal.
She'd been hosting the successful AM Chicago, a half-hour morning talk show, when friend and movie critic Roger Ebert persuaded her to go for it.
She knew she could make far more money but worried that "if your show isn't successful in syndication, you're off the air in three months," Ebert wrote in 2005.
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Winfrey completed the deal during a break in filming 1985's "The Color Purple" and received a $1 million signing bonus (which would be a rounding number on her current net wealth).
"I'm thrilled at the prospect of beating Phil Donahue throughout the country," she said at a post-signing news conference.
That seemed a long shot; Donahue's show dominated daytime talk. "We wanted someone different," Michael King said in 2007. "Oprah Winfrey was doing a great job hosting AM Chicago, and it goes without saying that she looked different."
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On September 8, 1986, "The Oprah Winfrey Show" debuted with a show titled "How to Marry the Man/Woman of Your Choice." Above is a photo of Winfrey interviewing Jimmy and Rosalynn Carter from an episode that aired June 5, 1987.
Time magazine wrote, "Few people would have bet on Oprah Winfrey's swift rise to host of the most popular talk show on TV. In a field dominated by white males, she is a black female of ample bulk. As interviewers go, she is no match for, say, Phil Donahue...What she lacks in journalistic toughness, she makes up for in plainspoken curiosity, robust humor and, above all empathy. Guests with sad stories to tell are apt to rouse a tear in Oprah's eye...They, in turn, often find themselves revealing things they would not imagine telling anyone, much less a national TV audience. It is the talk show as a group therapy session."
Martha Bayles of The Wall Street Journal said, "It's a relief to see a gab-monger with a fond but realistic assessment of her own cultural and religious roots," while Newsday's Les Payne noted, "Oprah Winfrey is sharper than Donahue, wittier, more genuine, and far better attuned to her audience, if not the world."
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While The Hollywood Reporter viewed Winfrey as "playfully belligerent" with a "charming sass," it didn't see much variation between her and Donahue.
"In choice of subject matter," said the review, "not too radically different from what Phil is presenting."
There would be one major difference, though: Winfrey transformed into a billionaire cultural icon; Donahue didn't.
But now a similarity has returned: talk show retirement.
"The Oprah Winfrey Show's" last original episode airs May 25.