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Shrewd and sharp, empathetic and disarming: How an Oprah interview went from must-see TV to cultural phenomenon

On March 7, over 17 million Americans watched Oprah Winfrey’s bombshell television interview with Prince Harry and his wife, Meghan, on CBS. (Video: Reuters)

A telephone ringing at 4:30 in the morning is rarely good news, so television executive Ted Harbert will never forget the day in 1993 that he was awakened at home in Los Angeles by a call from his boss, ABC Network Television Group President Bob Iger. When Harbert answered the phone, Iger uttered one phrase: “56 share.”

In other words, the previous night’s Oprah Winfrey interview with Michael Jackson — the pop icon’s first sit-down in 14 years — had been a ratings bonanza. A 56 share meant that 56 percent of households watching TV at the time were tuned in to the interview, a jaw-dropping amount that also translated into 62.3 million viewers. It remains one of the highest-rated non-Super Bowl broadcasts in TV history.

The special also cemented Winfrey’s reputation as one of the best interviewers in the business — a fact that garnered renewed attention this week after Prince Harry and Meghan, the Duke and Duchess of Sussex, dropped bombshell after bombshell in an explosive interview with Winfrey on Sunday night on CBS. The next day, the Internet was abuzz with the horrifying revelations, including the royals declining to offer help to Meghan when she suffered from suicidal thoughts and Harry’s conversation with a family member who expressed concern about the darkness of his son’s skin color.

The next most-discussed topic, however, was Winfrey herself. In news articles and on social media, viewers dissected her “master class” in interviewing. They focused on her shrewd ability to zero in on the most important details, as well as ask follow-up questions that elicited shocking responses, while expressing empathy and appearing so personable that viewers felt invested.

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“I’m not just saying this because we’re good friends, but it was so conversational. I thought you were perfection,” “CBS This Morning” co-anchor Gayle King — Winfrey’s longtime confidante — told Winfrey during a follow-up segment on Monday. “I felt like we were sitting in the room and we were just sort of eavesdropping in on a conversation. And that takes great skill.”

“We forgot just how good Oprah is at interviewing,” Al Roker said on NBC’s “Today” show. “Nobody could have gotten all of that like Oprah did.”

“Forgot” may be a bit strong, given that Winfrey’s expertise is on full display over on Apple TV Plus with “The Oprah Conversation,” where she’s hosted former president Barack Obama and Mariah Carey, among others, and on Discovery Plus, where her interview series “Super Soul” launched this month. But relatively new streaming services are not the same as a prime-time network slot, so this was a powerful reminder.

“There’s nothing like the reach of a broadcast TV network,” said Harbert, who stepped down as NBC Broadcasting chairman in 2016 after 40 years in the TV industry, including serving as ABC’s president of entertainment. And Winfrey is well aware of the power of the platform: Nearly 18 million people in the United States tuned in to see Meghan and Harry, making it the most-watched entertainment special since last year’s Academy Awards.

Harbert recalled meeting with Winfrey in 1993 before she sat down with Jackson and said she had an “awe-inspiring” level of preparation for the interview itself, as well as for the scheduling, promotion and production. And it’s obvious that little has changed in terms of her attention to detail.

“I think that showed back then, it showed on her television show, and it showed on CBS on Sunday night,” Harbert said.

Winfrey’s hugely successful, groundbreaking syndicated daytime talk show, which ran from 1986 to 2011, peaked in the early 1990s, averaging about 13 million viewers an episode. Though she eventually became a practically required stop for A-list celebrities — especially if they were on some sort of redemption tour — she sharpened her skills over the years by also spending years talking to everyday viewers, both onstage and in her audience. Even with her increasingly enormous wealth and power, she still felt relatable.

“She has this unique quality to just connect with people — any type of person, really. That’s a true gift,” said Miki Turner, an associate professor of professional practice at the University of Southern California’s Annenberg School for Communication and Journalism. She noted that Winfrey’s empathy and personal interactions endear her to her guests. “There’s something about her that makes people want to spill all of their tea.”

Turner thought Winfrey’s Harry and Meghan interview was “good” but wished Winfrey would have kept prodding into certain topics, such as Harry’s strained relationship with his father and brother. Still, Turner said she was glad that Winfrey let the couple take the reins of the discussion.

“One of the things I noticed in the past was, she sometimes didn’t really let her guests control the narrative because she would inject herself into the conversation, and it became about her, almost,” Turner said. “But she sat back, and she listened. And she seemed genuinely shocked at some of the things they said.”

Winfrey’s reactions, such as her stunned “What?” after Meghan revealed the conversation about Archie’s skin color, and her variety of shocked expressions at the couple’s revelations have already turned into memes.

“She asks the questions that you as a viewer really want, and she does it in a way that’s so disarming, and it feels like you’re on the journey with her,” said Pat Fili-Krushel, the former ABC network president and NBCUniversal News Group chairwoman. “Journalists aren’t supposed to show how they’re feeling — and she’s not really a journalist, though she definitely is one of the best interviewers. … And because of that, she can emote.”

Plus, Fili-Krushel said, viewers are so accustomed to seeing her on TV from her years on her talk show that even if they don’t realize it, there is an added level of relatability that automatically makes the interview more intriguing.

“When someone is on TV in your living room five days a week, you think you really know this person,” she said. “You can’t underestimate how accessible that makes her.”

High-profile figures appear to feel the same way because Winfrey has racked up a long list of notable sit-downs: Tom Cruise famously jumped on her couch over his excitement about dating Katie Holmes. Kim Kardashian was candid about her 72-day marriage. Author James Frey admitted he fictionalized his memoir. Lance Armstrong opened up about his doping scandal. Whitney Houston talked about her drug addiction.

“Celebrities trust her, and I think they realize the power of her brand,” Turner said. “If you want to get something out there, who do you go to? You go to Oprah.”

Winfrey has also maintained her reputation as someone who can handle extraordinarily sensitive topics. In 2019, HBO aired the two-part documentary “Leaving Neverland,” which told the story of Wade Robson and James Safechuck, who said Michael Jackson sexually assaulted them as children. Winfrey wound up interviewing Robson, Safechuck and director Dan Reed for a special after the film aired and told the audience she knew she would get backlash. But she said the story was bigger than Jackson because it involved the critical (and under-discussed) subject of childhood sexual abuse.

Reed vividly remembers sitting onstage with Robson and Safechuck, who were the main focus of Winfrey’s questions. “She has a tremendous authority, which you feel immediately,” Reed said. “And she feels like someone who’s on a level with you, that you can be open to and be sincere with and trust.”

At a dinner with Robson and Safechuck following the taping, Reed recalled Winfrey standing to deliver a brief speech, which Reed said contained “the rhetorical power that a really good preacher has.” It was already the end of an emotional day, he said, and soon all three men were in tears.

“She’s totally unafraid, but also very thoughtful,” Reed said. “She’s just a force to be reckoned with.”