She might be a media mogul, billionaire and national treasure, but even Oprah Winfrey makes mistakes. The first lady of daytime television is one of the most admired and respected talk show hosts ever to grace the small screen in the United States. Yet she still regrets her interview with revered American actress Sally Field to this day. Why? It appears as though “Lady O” just went too far...
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.
The infamous royal interview
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.