In the show’s final decade, Oprah and her team staged massive spectacles of increasing grandiosity, from the infamous car giveaway to a 21,000-person flash mob that shut down part of Chicago.
“It had become increasingly more difficult to top what you’d done the year before,” Oprah told WBEZ’s Jenn White. “I mean, to the point where we literally sat in a room saying ‘What about outer space?’ ”
That’s what we look at now: Oprah living her life at the top, pushing the boundaries of what could be done with the world’s most powerful talk show, and why it all had to end after 25 years.
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Oprah on the surprise Michigan Avenue flash mob in her honor in 2009
“Yeah, that’s the best surprise ever. That’s the best surprise ever, that I was trying to figure out 'What is going on here? What is going on?’ And then I notice all these people start dancing. ‘What is happening?’
“And when I finally got it, that’s just the greatest surprise ever.”
Oprah on deciding to gift 276 new cars to a live studio audience
“I just thought, ‘How are we gonna give away cars? And why would I give away cars? Is a car my favorite thing? Really?’ Cause for me, everything I did, and continue to do, has to have the basis of truth in it. Otherwise, it doesn't work. It just becomes a thing.
“So when we sat down and started to talk about the car giveaway, I said, ‘How do we find people who really need cars?’ That would make it really worth it to me. There would be a depth and intention. What’s our intention in giving away the cars?
“Intention is my favorite word. The producers will tell you. They were like ‘Intention? We’re giving away cars! Why do you need intention? The intention is the person ends up with a car!’
“I go, ‘Well, what if we find people who actually are in circumstances where the car will make a big shift in the trajectory of their work and life being, you know?’
“That’s a reason to do a car show.”
Executive producer Lisa Erspamer on the backlash from the car giveaway
“It was devastating after because gift tax is a thing. I don’t know if you know about gift tax. It’s always a complicated thing when you’re giving stuff away.
“We paid for the sales tax and registration and we told the audience after that if they didn't want to have to pay a gift tax, they could actually take cash for the car. And because we didn't pay the gift tax, people complained to the press.
“And that was devastating.”
Oprah on why the show’s 25th season would be its last
“I knew that if I continued at the pace that I was going that I would not be able to maintain the level of quality. You’d have to lower your standards in order to keep the volume going because you’re now competing with everything. You’re competing with the internet and bloggers and YouTube and ... just too much. So what you have to do to keep running faster and faster and faster and making it bigger and bigger and bigger.
“I feel that there wasn't another thing to say in a way that we hadn’t said it. And I never wanted to be at the point where people would say, 'Oh, she should have stopped that show two years ago. It used to be good, but now I don’t know what they’re doing over there.’
“So I never wanted that and I never wanted to be in a position where I did not want to come to work.”
Director of audience services Sally Lou Loveman on the effect of attending The Oprah Winfrey Show
“I loved seeing people's faces when they walked in the door and they screamed and they held onto the person that they loved the most. And that -- I have chills when I talk about it -- that is what I loved about that television show. “Whether people left the studio with, you know, a CD or a compliment from Oprah, they always left with bigger hearts.”