10 of Oprah’s most iconic celebrity interviews of all time after Harry and Meghan’s bombshell interview

Jessica Benjamin
·5 min read
<p>Sarah Ferguson tells all on Oprah’s couch</p> (AP)

Sarah Ferguson tells all on Oprah’s couch

(AP)

If there’s someone who’s famous for getting people to talk, it’s Oprah.

So famous in fact, ‘Oprahfication’ has come to mean public confession as a form of therapy. And when it comes to Oprah, no one gets away lightly – not even celebrities.

A-listers from Rihanna to Fergie (Duchess of York, not the Fergalicious singer) have opened up their hearts sat atop Oprah’s confessional couch – and now, Harry and Meghan have done the same.

The tell-all interview will go down in history, so we’re taking a look back at her other iconic celeb interviews through the years.

James Frey, 2006

Not just an interview wizard and car gifting extraordinaire, Oprah has proven herself to be a dab hand at fraud exposure. James Frey, author of ‘memoir’ A Million Little Pieces, went on the show in 2006 to admit the fact that actually, most of it was made up. Luckily for Oprah, her interview with Frey redeemed the small issue of her choosing his novel for her book club and subsequently propelling it on to the best seller list. Oops.

Iconic quote: ‘Did you cling to that image because that’s how you wanted to see yourself, or did you cling to that image because that would make a better book?’

Whitney Houston, 2009

Amid a very public substance abuse battle, Whitney Houston gave her first interview in seven years to Oprah – and one of the last interviews she’d give in her life. For the first time, the singer opened up about her abusive relationship with Bobby Brown and her struggles with drug addiction and rehabilitation, laying herself bare for both Oprah and the world to see.

Iconic quote: ‘We were lacing our marijuana with base. We weren’t on crack. We weren’t on no crack stuff. We weren’t buying $20 jumbos. We were paying money.’

Tom Cruise, 2005

Tom Cruise being weird is the standard Tom Cruise we know and love (sort of). But his interview with Oprah in 2005 has spawned so much viral content it’s hard to ignore. Jumping up on the sofa and pro-claiming ‘I’m in love!’ with his then-girlfriend Katie Holmes would be kind of sweet, except for the fact that they’re now divorced. Oh well.

Iconic quote: ‘He’s gone. He’s gone. The boy is gone.’

Michael Jackson, 1993

It’s the most watched television interview of all time with 90 million viewers – and with good reason. After 14 years of refusing interview access (there’s a running theme here), he opened the gates of Neverland to Oprah – because who else would it be? Asking the questions on everyone’s lips, from plastic surgery to father-son relationships, Oprah’s interview with Jackson went down in candid celeb history.

Iconic quote: ‘When people make up stories that I don’t want to be who I am, it hurts me.’

Lance Armstrong, 2013

Emotional revelations aside, Oprah has also made considerable headway in confessions of wrongdoing. The famous Lance Armstrong interview of 2013 saw the cyclist finally admit defeat in his doping scandal, answering Oprah’s quick-fire questions in a manner more fitting of a courtroom than a chat show. Armstrong subsequently lost $75 million of sponsorship in a day. Ouch.

Iconic quote: ‘My ruthless desire to win at all costs served me well on the bike but the level it went to, for whatever reason, is a flaw.’

Ellen DeGeneres, 1997

After coming out as her fictional character on ‘Ellen’, the real Ellen took to Oprah’s show to announce that she too was gay, and garnered mixed responses from worldwide audiences. Oprah herself received the most hate mail she’d ever been sent as a result – but the episode has gone down in TV and LGBTQ history.

Iconic quote: ‘Why did you think it was necessary for you to come out?’ ‘Because it’s ok.’

Sarah Ferguson, 1996

Meghan and Harry aren’t the only royals on the talk-show block. In 1996, Fergie gave a candid account of her life as a Duchess, giving Oprah audiences a glimpse behind the doors of Buckingham Palace and the reality of living a fairy-tale – as well as Diana’s misery.

Iconic quote: ‘The British Press is cruel, abusive and utterly invasive’

Trump, 1988

In an interview that could be a carbon copy for one of his campaign trail speeches, Trump took to Oprah’s sofa in 1988 to air his views on foreign policy and making American allies pay their dues. Despite being on the show to promote his new book, Trump could never resist an opportunity for good old-fashioned profiteering, prompting Oprah to ask if he’d ever run for president. Who, me?!

Iconic quote: ‘I think I’d win. I’ll tell you what: I wouldn’t go in to lose.’

Rihanna, 2012

After the infamous photos surfaced and Chris Brown received five years’ probation and a restraining order against her, Rihanna’s interview with Oprah in 2012 shocked the world. The singer spoke of forgiveness, friendship and peace – a far cry from her 2009 tabloid headlines.

Iconic quote: ‘Now we’re very very close friends. We’ve built up a trust again, and that’s - we love

The Obamas, all the time

It’s no secret that the Obamas and Oprah are great friends. After endorsing his 2008 presidential campaign, the ‘Oprah effect’ was thought to have won Obama a million more votes – and they’ve been together through thick and thin ever since. Their latest appearance was achieved via green screen (thanks, Covid), but still lived up to the sky-high Oprah standards.

Iconic quote: ‘[Biden and Harris will] re-establish that there’s an expectation that the president doesn’t routinely lie.’