How would Oprah Winfrey have handled Bruce Jenner's powerful interview with 20/20?
The 61-year-old legendary talk show host puts the question out there in a new interview with Women's Wear Daily, admitting that she wanted to do the groundbreaking sit-down with the 65-year-old former Olympian.
"There are only a few [interviews not over in an instant]," Oprah says. "I wanted Bruce Jenner. Diane [Sawyer] got it. That's great but there are few. There are only a few [interviews], but you're not going to be able to think about it."
While the interview was a huge ratings hit -- it was watched by over 17 million people -- even Oprah has to admit that it’s hard to think of new, exciting subjects to talk to.
"The problem is, and even now, because I started doing this with Next Chapter, there's nobody -- try to think of somebody -- who would be willing to do an interview on a regular basis that you can't go and Google and find out what has happened to them in the past week. There's nobody," she tells WWD about why she doesn't miss interviewing people.
Perhaps thinking about her missed opportunity, Oprah reflects on her past coverage of transgender issues in the candid new interview, and says she feels she could have done a lot more.
"I was in a conversation a couple of days ago and someone said: 'You know, we were talking about the whole issue of transgender and how it has become so accepted now, and somebody said, 'You know the Oprah show, I think has had a big impact,'" she recalls. "I said, 'I don't think so.' We did several transgender [shows], but we didn't do as much for transgender as I did for, say, abused kids or battered women. And they said, 'But no, you started the conversation. You started the conversation and the conversation has led us to here.'"
As for her future, the Selma actress doesn't see herself covering O Magazine every month like she has for the past 15 years.
"We actually seriously considered it [the end of her reign on the cover] for now, and made the decision not to do it now," she surprisingly reveals. "I'm amazed that we don't run out of ideas. I'm amazed at the number of poses that I've been able to do. I'm amazed that there's still a way to clap my hands, smile or raise a thumb. I don't have another clap in me, or another smile or another way to turn my head to the left. There's not enough wind machines."
Watch the video below to revisit Oprah's seven most important O Magazine covers.