When Oprah Interviewed Sally Field, She Made One Of The Biggest Mistakes Of Her Career

Winfrey admitted on Rob Lowe’s Literally! podcast in May 2021 that there’s one interview memory that still makes her coil up. And it was the time that she dared to ask a probing question about Field’s relationship with the late movie star, Burt Reynolds. The outcome? Well, let’s just say that the actress didn’t respond too well.

“I cringe to even think that I asked that question,” the talk show legend admitted to Lowe. And we’re squirming at the thought too. Because the moment has to be up there with some of the worst cases of car-crash TV. But it’s not like Winfrey is a stranger to awkward interviews. There were her now infamous conversations with Michael Jackson and Lance Armstrong, for example. 

Then there’s the celebrated star’s interview with Prince Harry and Meghan Markle, which became the talk of the planet. Winfrey secured the exclusive – and explosive – conversation as a personal friend of the Royal couple’s. This is a claim she can make of many an A-lister, following an illustrious career in television that has spanned more than four decades.

Perhaps one reason that the TV icon is so revered, is because she battled through childhood adversity to reach the top. Winfrey was born in the rural community of Kosciusko, Mississippi, where she lived with her grandmother in poverty for several years. Things didn’t get any easier during her pre-teens either, as the youngster was passed between her troubled mother Vernita in Milwaukee, and father Vernon in Nashville.

Winfrey later revealed that she suffered abuse by a number of relatives and friends while growing up. She also claimed that her family refused to believe her about it. But the resilient star defied the odds to become a high school honors student. Her burgeoning talent for broadcasting also earned her a junior news anchor position with a local radio station.

The young Winfrey later achieved fame as both the youngest news anchor and first black female reporter on Nashville’s WLAC-TV channel. She then secured her first TV talk show job with AM Chicago in 1984. And her popularity with viewers soon led the show to knock Donahue off the top spot in the ratings.

The program drew such a large audience, in fact, that it was extended to one hour and renamed The Oprah Winfrey Show. Los Angeles Times critic Howard Rosenberg wrote, “She’s a roundhouse, a full course meal, big, brassy, loud, aggressive, hyper, laughable, lovable, soulful, tender, low-down, earthy, and hungry. And she may know the way to Phil Donahue’s jugular.”

The show had already made Winfrey a millionaire by the end of its first year. And seeing its money-making potential, the savvy star seized ownership from ABC and placed it under the control of her own company, Harpo – “Oprah” spelled backwards – Productions. The program went on to become a sensation abroad, too.

So what was the secret to The Oprah Winfrey Show’s success? Perhaps it was because, as Martha Bayles of The Wall Street Journal, put it, “It’s a relief to see a gab-monger with a fond but realistic assessment of her own cultural and religious roots.” Or maybe because the TV icon eschewed the talk-show trend of focusing on trashy tabloid subjects.

Throughout the series’ 25-year run, from 1986 to 2011, Lady O continued to cultivate her brand. “Oprah’s Book Club” was hugely influential in bestseller lists. And “Oprah’s Favorite Things” – the icon’s annual compilation of holiday gift ideas – eventually began selling on the Amazon website. Then there was her show giveaway to end all TV show giveaways… Where every member of her audience in a 2004 episode got a car!

Yep, all 276 people attending that day – handpicked because they all badly needed a car – were in raptures after Winfrey famously announced, “You get a car!” The excitement at being given a freebie Pontiac G6 was apparently enough to require emergency medical staff on standby in case anyone went into cardiac arrest through sheer joy. Now you can’t say that about many TV shows.

The TV legend consistently ranks in the top ten greatest talk show hosts of all time. And she recently scored perhaps the most high-profile interview of her career, with Prince Harry and Meghan Markle. Let’s face it, you’d have to have been living in an underground dwelling not to have heard about that one.

The Duke and Duchess of Sussex referred to the royal family as “The Firm,” during the interview, with Markle saying she’d had suicidal thoughts. The Duchess also claimed that she’d had no support from the royal family. Perhaps most shocking of all, though, was their claim that a member of the royal household had expressed concern over the colour of their son’s skin, before he was born.

So what makes Winfrey the kind of interviewer that A-listers feel comfortable confiding in? Well, psychotherapist and host of the Verywell Mind podcast, Amy Morin, explored that very question. In an article for the Business Insider website, Morin examined seven of the TV legend’s interview techniques, and how she gets the stars to open up.

The psychotherapist explained, “Oprah’s interviewing skills have stood the test of time because she strikes a great balance between helping guests feel like they’re part of an intimate conversation, while also helping her audience feel like they’re part of the interview.” And it starts with being comfortable with silence, says Morin. 

“The pause is often a sign that a guest is hesitating to share more information,” said Morin. “When there’s an awkward silence, however, most guests will be eager to fill it – even if that means chiming in with the rest of a story that they’re hesitant to tell.” 

Winfrey also strikes the balance between being direct yet non-confrontational in her questioning. And she uses the technique of “reflective listening” – repeating back what’s just been said – to show that she’s really listening to her guests. “It’s about reflecting back what you hear to show you’re trying to truly understand,” Morin told Business Insider.

Instead of relying on a list of questions, the host is natural in her interviewing approach, too. Winfrey bounces off guests’ comments with follow-up questions, as Morin explained, “She shows she’s interested in taking a deeper dive into their wisdom and their experiences.” And she’s not afraid to go into uncharted territory either.

Body language, too, plays an important part in Winfrey’s success, wrote the psychotherapist. The host has perfected the art of leaning in to listen intently to her guests. As Morin explained, “Leaning forward in her chair when they’re sharing raw emotion sends a clear signal that she’s with them and wants them to keep going.”

But for all her professionalism, Winfrey has still made a few gaffes along the way. And her show has seen some cringeworthy moments, too. Like the time Tom Cruise made us all squirm by jumping up and down on her sofa. But while most of us found the star’s eccentric display pretty odd, Lady O simply remarked, “I did not think it would turn into the brouhaha that it did.”

Then there was the time she called out James Frey in 2006 for embellishing parts of his dramatic life story, A Million Little Pieces. Having previously promoted the autobiography in her high-profile Book Club, Winfrey accused the former drug addict of being “a false person.” But the host later backtracked and invited Frey back on her show in 2011 to apologise.

And we can’t forget when Winfrey interviewed cyclist Lance Armstrong in 2013. The former Tour de France champion had been banned from his sport due to performance-enhancing drugs. But instead of showing remorse, Armstrong made an awkward attempt at humor. The joke was at the expense of one of the people who blew the whistle on his drug-taking, Betsy Andreu.

Armstrong recalled a conversation he had had with the wife of ex-teammate Frankie Andreu. He told Winfrey, “I said, ‘Listen, I called you crazy. I called you a [something]. I called you all these things, but I never called you fat.’” Armstrong then paused, clearly expecting a laugh. But his interviewer returned a killer icy look instead. Awkward!

Lady O arguably overstepped the mark while interviewing the late King of Pop, Michael Jackson, back in 1993. The troubled megastar opened the doors of his Neverland Ranch for the TV icon. But he probably wished that he hadn’t, when Winfrey dared to ask him if he was a virgin. The Thriller singer awkwardly replied, “How can you ask me that? I’m a gentleman.”

Then there was the ultimate blunder. The moment that Winfrey described as the one “big mistake” in her long and illustrious career. And it was during an interview with fellow American sweetheart, Sally Field. Winfrey recalled the encounter while speaking to Rob Lowe on his Literally! podcast in 2021. During which the Parks and Recreation star mentioned Fields’ late love, Burt Reynolds.

This prompted Winfrey to pipe up with, “Oh, gosh! I have a Burt Reynolds story.” And she told Lowe that while interviewing Field years ago, she had brought up the actress’ relationship with Reynolds. The couple had dated for five years after meeting during the making of Smokey and the Bandit in the 1970s. And as Winfrey recalled, “My big mistake: I asked her, ‘Does Burt sleep with his toupee on?’”

Winfrey went on, “I even say now, I cringe to even think that I asked that question. But I asked it because the producers are like, ‘You have to ask. That’s what everybody wants to know.’ And so I asked it, and she went cold on me. She shut down, and I could not get in again.”

A sympathetic Lowe agreed that the Mrs Doubtfire actress was capable of going cold. Recalling his experience working with Field on TV drama Brothers & Sisters, he said, “She’s one of the most amazing actors I’ve ever known, but when Sally goes cold, it’s like Khrushchev in the Cold War. She will bury you.” To which Winfrey responded, “I deserved it, ‘cause that is such an inappropriate question.”

Clearly it was a sensitive subject for the Smokey and the Bandit star. Which begs the question, why? Well, a five-year relationship clearly suggests that the couple were pretty serious about each other. Plus the split was a painful one for Reynolds who, before his passing, spoke of his deep feelings for Field.

The late star told British newspaper The Daily Mail in 2016 that Field was “the love of my life.” Their separation was his “biggest disappointment,” Reynolds said, adding “That sense of loss never goes away.” The actor went on, “I have no idea what Sally thinks about it. She could pick up the phone and speak to me but she never does.”

But Field stayed silent until the release of her autobiography, published just weeks after Reynolds’ death in 2018. In the memoir entitled In Pieces, the actress opened up about her difficult relationship with him. She told The New York Times in 2018, it was “confusing and complicated, and not without loving and caring, but really complicated and hurtful to me.”  

The actress also admitted that she was glad that Reynolds would never have the chance to read her memoir. Field explained to The Times, “This would hurt him...I felt glad that he wasn’t going to read it, he wasn’t going to be asked about it, and he wasn’t going to have to defend himself or lash out, which he probably would have.”

The Oscar-winning star shockingly revealed in her memoir that she had been abused by her stepfather as a child, which had damaged her relationships with men. Reynolds being among those men. Discussing her memoir, Field explained to NPR, “I reveal...what I was feeling and how trapped I was in an old pattern of behavior — and how I was predisposed.”

The actress continued, “He was a preformed rut in my road. And I couldn’t see it coming and I didn’t know how to get out. I had been carefully trained to fall into this...We were a perfect match of flaws.” That flawed relationship included Reynolds refusing to support his partner when she wanted to attend the 1977 Emmys.

That night Field won the outstanding lead actress gong for the 1976 TV series Sybil. But as she told NPR, she didn’t attend. “My predisposition [is] ...to try to not be seen ...to not speak up and say: ‘Look, this is important to me. I’m going to do it.’” But she continued, “I couldn’t do any of that. So I ended up watching it alone in the rented condo with the sound turned down.”

Field heartbreakingly confessed, “[There are] patterns that get set up in your life that as an adult you have to work your whole life to try to untangle. Because they might be survival patterns when you’re a child, but as an adult they completely get in your way and they’re unproductive.”

She went on, “As a child, because of my relationship with my stepfather ...in my mind, to be seen, to be loved, I also had to be terrified and I couldn’t ever say what I was really feeling. So I had to be invisible.” But clearly the actress’ feelings for Reynolds ran deep, as she admitted to The Times that she was “flooded with feelings and nostalgia” after hearing of her former flame’s passing.

And despite going on to get married twice – the Forrest Gump star admitted that she would never forget her former love. In a statement following Reynolds’ death, Field wrote, “There are times in your life that are so indelible, they never fade away. They stay alive, even 40 years later. My years with Burt never leave my mind.”

So it isn’t surprising that Field reacted the way she did to Winfrey’s question about Reynolds, given their backstory and heartache. Wouldn’t anyone react strongly to probing, flippant questions about their ex-partner? Which just goes to show that even the greats can make some pretty sizable slip-ups.