Oprah Winfrey has interviewed more than 37,000 people in her six-decade career. Getty Images
Oprah Winfrey has interviewed more than 37,000 people in her six-decade career. Getty Images
Oprah Winfrey has interviewed more than 37,000 people in her six-decade career. Getty Images
Oprah Winfrey has interviewed more than 37,000 people in her six-decade career. Getty Images

7 of the most memorable Oprah Winfrey interviews ever


Sophie Prideaux
  • English
  • Arabic

Oprah Winfrey has, in her five-decade career, conducted more than 37,000 interviews. Among those to join her on the sofa of The Oprah Winfrey Show have been some of the world's biggest names. From presidents to Hollywood greats and everything in between, there have been plenty of shocking and memorable moments.

And as it is announced the talk show host will sit down with the Duke and Duchess of Sussex in March, for their first interview since stepping back as senior members of the British royal family, the world waits with bated breath to hear what they will have to say.

Until then, here are seven of the biggest interviews Oprah has done over the years:

Michael Jackson

In 1993, Winfrey was personally invited to Michael Jackson's Neverland Ranch for an interview with the notoriously private star. The interview went on to become the most watched in television history, thanks in part to the Thriller star's unusual openness, which saw him discuss everything from his relationship with his father to his skin condition, vitiligo.

Sarah Ferguson, Duchess of York

Former wife of Prince Andrew, Sarah Ferguson, the Duchess of York, has been interviewed by Oprah on a number of occasions. However, the most notable was her 1996 appearance on The Oprah Winfrey Show – the year of her divorce – in which she spoke of the breakdown of her marriage, and was critical of the British media, calling them "invasive" and "cruel". She was also interviewed in 2011 after British tabloid News of the World leaked video footage of her accepting a bribe in exchange for access to Prince Andrew the year before.

Tom Cruise

In 2005, Tom Cruise provided one of the most talked-about moments in the history of The Oprah Winfrey Show when he famously leapt on to the couch to declare his love for then-girlfriend Katie Holmes. The hyperactive, chaotic interview with Cruise – who was arguably one of Hollywood's biggest stars at the time – was one of the first videos to truly go viral on newly-launched YouTube, and would provide enough gossip page fodder to keep columnists in business for months.

Whitney Houston

In 2009, Oprah sat down with Whitney Houston for what became one of her most shocking interviews ever. The singer got candid about the breakdown of her 14-year marriage to Bobby Brown, discussing alleged infidelity as well as emotional and physical abuse. She also spoke of her struggles to overcome addiction.

Barack Obama

Then-US president Barack Obama and the first lady, Michelle Obama sat down with Oprah in 2011, becoming the first sitting president to appear on the show. For the interview, the trio took a trip to the Obamas's hometown of Chicago. President Obama opened up about his love for his wife and children, and Oprah admitted it was one of only a small handful of times she felt nervous to interview one of her guests, describing it as an "out of body" experience.

Rihanna

For Oprah's Next Chapter in 2012, Rihanna took Oprah on a tour of her childhood neighbourhood in Barbados, before sitting down for a lengthy chat in which she discussed the violence she experienced at the hands of her former boyfriend, R'n'B star Chris Brown.

Speaking of the media circus that followed the incident, an emotional Rihanna said: “It was a weird space to be in, because 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 is going to say he needs help, everybody is going to say he is a monster.”

Lance Armstrong

After years of denying allegations, in 2013, Lance Armstrong finally admitted to using performance-enhancing drugs in cycling races. He sat down with Oprah for a tell-all interview, where he addressed the controversy for the first time on camera. He revealed he had used the drugs to win all seven of his Tour de France titles, and claimed that doping was so prevalent in the sport at the time, that it would have been impossible to win without them.

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Timeline

2012-2015

The company offers payments/bribes to win key contracts in the Middle East

May 2017

The UK SFO officially opens investigation into Petrofac’s use of agents, corruption, and potential bribery to secure contracts

September 2021

Petrofac pleads guilty to seven counts of failing to prevent bribery under the UK Bribery Act

October 2021

Court fines Petrofac £77 million for bribery. Former executive receives a two-year suspended sentence 

December 2024

Petrofac enters into comprehensive restructuring to strengthen the financial position of the group

May 2025

The High Court of England and Wales approves the company’s restructuring plan

July 2025

The Court of Appeal issues a judgment challenging parts of the restructuring plan

August 2025

Petrofac issues a business update to execute the restructuring and confirms it will appeal the Court of Appeal decision

October 2025

Petrofac loses a major TenneT offshore wind contract worth €13 billion. Holding company files for administration in the UK. Petrofac delisted from the London Stock Exchange

November 2025

180 Petrofac employees laid off in the UAE

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Avatar: Fire and Ash

Director: James Cameron

Starring: Sam Worthington, Sigourney Weaver, Zoe Saldana

Rating: 4.5/5

If you go

The flights
Emirates and Etihad fly direct to Nairobi, with fares starting from Dh1,695. The resort can be reached from Nairobi via a 35-minute flight from Wilson Airport or Jomo Kenyatta International Airport, or by road, which takes at least three hours.

The rooms
Rooms at Fairmont Mount Kenya range from Dh1,870 per night for a deluxe room to Dh11,000 per night for the William Holden Cottage.

Afghanistan fixtures
  • v Australia, today
  • v Sri Lanka, Tuesday
  • v New Zealand, Saturday,
  • v South Africa, June 15
  • v England, June 18
  • v India, June 22
  • v Bangladesh, June 24
  • v Pakistan, June 29
  • v West Indies, July 4
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