80 Years of The Hollywood Reporter

AP Photo/Charlie Knoblock

The most glamorous and memorable moments from a storied history.

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 you're show isn't successful in syndication, you're off the air in three months," Ebert wrote in 2005. She completed the deal during a break in filming 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." While The Hollywood Reporter viewed Oprah 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: She transformed into a billionaire cultural icon; he didn't. But now a similarity has returned: talk show retirement. The Oprah Winfrey Show's last original episode airs May 25.