Oprah before Harry and Meghan: her most memorable and revealing interviews
Will Meghan leap onto a sofa? Will Harry crumble and cry? Stranger things have happened in an Oprah Winfrey interview.
Speculation has begun as to what stirring emotional moments and juicy personal revelations will come out of the Duke and Duchess of Sussex’s interview with their personal friend and American celebrity interviewer, which will air in the UK on ITV on Monday evening.
We can expect the Oprah effect to work its characteristic magic; in a teaser clip released by CBS, she remarks to the couple: “you have said some pretty shocking things here.”
Over the course of a 25-year career that took her from an impoverished childhood in rural Mississippi to become the wealthiest African American of the 20th century, Winfrey has sat across from some of the most prominent politicians, actors and singers in the world, and quietly charmed them into bearing their souls.
From Lance Armstrong’s guilt to Rihanna’s forgiveness, for some of the most memorable moments in modern pop culture, you need look no further than Oprah’s sofa.
Michael Jackson, 1993
Years before the horrifying abuse allegations that have forever tainted the pop star’s name, Oprah’s interview with the reclusive Michael Jackson remains the most watched television interview in history, drawing 90 million viewers, and was, according to Oprah, the most exciting interview she has ever done. Fourteen years after his last public press appearance, Jackson invited Oprah to his now infamous mansion, Neverland.
She addressed him directly about his altered skin colour – “Are you bleaching your skin? Is your skin lighter because you don’t like being black?” – in answer to which he spoke for the first time about suffering from vitiligo, a skin disorder that destroys pigmentation in his skin. He also discussed his abusive father, the trauma of a childhood spent going out to work, and admitted to having had a nose job.
Sarah Ferguson, 1996
The Duke and Duchess of Sussex aren’t the first disenchanted royals to open up to Oprah. Four years after her split from Prince Andrew, and just after the official announcement of their divorce, Fergie spoke unsparingly about life as a Duchess within the Firm: “it’s not a fairytale, it’s real life in there, so to speak, or they think it’s real life.” She discussed the micromanagement of life in Buckingham Palace, right down to the prescribed limits on the wattage of the light bulbs, and the treatment of Diana (who she described as her best friend) at the hands of the media. The tabloids “have tried to kill her” said Oprah, with what now feels like tragic dramatic irony, and Fergie agreed: “the British press is cruel, abusive, and so invasive.” How times have changed for those who marry into the royal family.
Ellen DeGeneres, 1997
Oprah’s interview with Ellen would go down in TV and LGBTQ+ history as her first public conversation after coming out on the cover of Time, after years of speculation about her sexuality. Hours after the interview aired, the character she played on her sitcom Ellen – a lightly fictionalised version of herself – also came out. The “Puppy Episode” was watched by an estimated 44 million people, nearly three times the show’s usual ratings. During her conversation with Oprah, she spoke with striking composure about how her father and stepmother had asked her to move out of their house after she told them, worried that she would “influence” her two young step sisters. “I understood it. I understand people not understanding” she said. Oprah says the most hate mail she has ever recieved came after that interview.
Tom Cruise, 2005
“I’m in love.” Oprah’s interview with the eccentric movie star is memorable more for his intense weirdness than any specific personal revelations. The conversation took place in the first romantic flush of Tom Cruise’s relationship with actress (and future wife) Katie Holmes and his obvious euphoria and sugar-high energy set the tone. It took a few minutes at the start for Oprah to persuade the audience, which seemed to consist almost entirely of young women, to stop screaming, and from there, things only got more manic. As Cruise gushed about his girlfriend, he punched the air, fell to his knees, and finally jumped onto the sofa, a moment that spawned a thousand Gifs, a Family Guy parody, and has been credited with fueling the rise of internet celebrity gossip culture.
James Frey, 2006
In a dramatic and revelatory u-turn (or an adept and face-saving publicity stunt, depending on your point of view), weeks after choosing A Million Little Pieces, a “memoir” of crime, addiction, and his journey to sobriety, for her book club, and subsequently propelling to bestseller lists, Oprah sat down with its author James Frey for a conversation in which he revealed that he had in fact fabricated large parts of it. It was an uncharacteristically angry performance from Oprah, who clearly felt personally affronted by the con. Later, she came to regret her harshness – “Over the years I’ve always tried to maintain a position of non-judgement and being able to find the thread of light, a way in, to see that person as human being and look at them with some sense of compassion and I did not do that with James Frey” – but the spectacular showdown, which left Frey struggling to defend himself, proved a television sensation.
Whitney Houston, 2009
The singer’s interview with Oprah was not only the first she had given in seven years but would turn out to be one of her last. Whitney Houston spoke for the first time about her abusive relationship with her husband Bobby Brown, acknowledging that he was jealous of her success, that she had consciously tried to “make herself smaller” to appease him, and that “somewhere inside, something happens to a man when a woman has that much control or that much fame.” She also spoke about her own, very public struggles with drug addiction – cocaine and marijuana were her substances of choices, she said – and experiences in rehab.
Three years after the singer Chris Brown received five years probation and a restraining order for violence against Rihanna – the grim evidence of which was leaked to the world via a police photograph – the pop princess surprised and angered many of her fans by telling Oprah that she had forgiven her abusive ex-boyfriend. “As angry as I was, as angry and hurt and betrayed, I just felt like he made that mistake because he needed help and who’s going to help him? Nobody’s going to say he needs help. Everybody’s going to say he’s a monster without looking at the source, and I was more concerned about him.” She also revealed that her father had been violent towards her mother during her childhood, but that she had now repaired her relationship with him as well.
Lance Armstrong, 2013
The disgraced former champion cyclist Lance Armstrong spoke to Oprah at the height of the doping scandal, after two decades of denying the allegations against him, and admitted for the first time that he had taken illegal performance enhancing drugs before all seven of his Tour de France wins. He also described himself as a bully with “a ruthless win-at-all-costs attitude.” Oprah’s quick-fire yes-or-no questions gave the chat show the feel of a courtroom drama and the effect of the TV event meant that Armstrong subsequently lost $75 million of sponsorship in a day.