These are the 10 most unforgettable Oprah Winfrey interviews of all time

As the world awaits Meghan and Harry's exclusive airtime with the presenter, take a look back at her most iconic celebrity interviews

Oprah Winfrey's best celebrity interviews of all time: Oprah Winfrey in the chair
(Image credit: Getty Images)

As the world awaits Meghan and Harry's exclusive airtime with the presenter, take a look back at her most iconic celebrity interviews

Everyone knows that Oprah Winfrey is the queen of celebrity interviews.

She's had everyone on her couch over the years, from Kim Kardashian, to Donald Trump, to Whitney Houston, and is known for her seemingly effortless ability to get even the most famous and sought-after celebrities to talk about topics they vowed they never would.

Next in line? The former Duke and Duchess of Sussex.

It feels like the whole world is waiting with bated breath for Monday evening, when Prince Harry and Meghan Markle will appear in an exclusive interview with the presenter.

In the pre-released preview of the episode, Oprah says '[I] want to make it clear to everybody that no subject is off limits', indicating that the couple will chat candidly about Meghan's relationship with the press, their move to the USA, and their step down as official Royals last year.

They haven't spoken about most of this publicly before.

In the UK, you'll be able to watch the two-hour special on Monday 8th March at 9pm on ITV. You can also view it online via the ITV Hub.

For now, we've got a whole load of Oprah's most iconic interviews for you to scroll through. Public service announcement: there's some good ones.

10 best Oprah celebrity interviews of all time

1. Kim Kardashian

Back in 2012, Kim did a tell-all interview with Oprah about her leaked sex tape with former partner Ray J. After the sex tape went viral, it has often been credited for making her and her other Kardashian siblings famous.

In the interview, she also discussed her short but sweet 72-day marriage to NBA player Kris Humphries and candidly answered Oprah's question about whether they got married as a stunt. With over four million views, it's certainly been watched a lot.

2. Donald Trump

Fun fact: one of the first times Trump publicly shared that he hoped to run for President one day was during an interview with Oprah back in 1988. In an interview that now has over seven million views, he discussed his dreams of Presidency and said: ‘I think I’d win. I’ll tell you what: I wouldn’t go in to lose.’

He actually went on her show to discuss his new book deal, put discussed foreign policy, war, and running for President, instead. Sounds about right.

3. Mike Tyson

Boxer Mike Tyson has one of the most-watched Oprah interviews of all time, at a staggering 9.9 million views on YouTube at current.

In the 2009 interview, the heavyweight champion emotionally discusses the highs and lows of his career. Tyson also gets choked up as he chats to Winfrey about his time in jail, the infamous fight with Evander Holyfield during which Tyson bit part of Holyfield's ear lobe clean off, and the death of his daughter.

4. Sarah Ferguson

The Sarah Ferguson interview with Oprah Winfrey back in 1996 was iconic for a number of reasons. She appeared on the show asking for forgiveness, having been caught in the middle of a bribery scandal for access to her ex-husband, Prince Andrew.

Not just that, but also opened up about the realities of life as a Duchess, the 'cruel, abusive and utterly invasive' British press, and Princess Diana, too. A must watch for Royal fans.

5. Barack Obama

The former President of the United States hasn't been interviewed by Oprah once, but a handful of times, in the run up to his election and since, to show his support of fellow Democratic candidate, Joe Biden.

6. Whitney Houston

Another skill Oprah is renowned for? Getting celebrities who don't normally talk, to talk.

Whitney Houston's 2009 interview is a good example of this - she hadn't spoken publicly for seven years, and opened up to the presenter about her drug addiction, , rehabilitation, and the domestic abuse she suffered at the hands of Bobby Brown.

It was also one of her last ever interviews she gave before her death in 2012.

7. Michael Jackson

Another celebrity who'd refused to be interviewed by anyone else - in this instance, for fourteen years - was singer Michael Jackson.

That is, apart from Oprah. He let the TV legend interview him at his Neverland home in 1993, where they discussed his plastic surgery, skin colour, and his own relationship with his father.

To date, it's had a huge 7.8 million views.

8. Rihanna

The whole world was shocked when images of a beaten-up Rihanna surfaced in 2009.

Her partner of the time Chris Brown was found guilty of abuse, and was given five years probation and a restraining order for physically abusing the pop star.

Speaking about the relationship candidly for the first time in 2012, Rihanna opened up to Oprah about Brown's violence, her childhood, and also, her forgiveness of him.

9. Ellen Degeneres 

Ellen chatting to Oprah was a stand-out moment for the LGBTQ+ community as it was her first big TV interview after coming out.

It was one of the first times she'd really discussed her sexuality publicly.

10. Tom Cruise

Last but by no means least is Oprah's 2005 interview with actor Tom Cruise. This was at the height of his romance with Katie Holmes - he jumps from Oprah's sofa and shouting ‘I’m in love!’. Yep.

Ally Head
Senior Health, Sustainability and Relationships Editor

Ally Head is Marie Claire UK's Senior Health, Sustainability, and Relationships Editor, nine-time marathoner, and Boston Qualifying runner. Day-to-day, she works across site strategy, features, and e-commerce, reporting on the latest health updates, writing the must-read health and wellness content, and rounding up the genuinely sustainable and squat-proof gym leggings worth *adding to basket*. She's won a BSME for her sustainability work, regularly hosts panels and presents for events like the Sustainability Awards, and is a stickler for a strong stat, too, seeing over nine million total impressions on the January 2023 Wellness Issue she oversaw. Follow Ally on Instagram for more or get in touch.