7 of Oprah Winfrey’s Most Memorable Interviews

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Over the course of her five-decade career, Oprah Winfrey has conducted over 37,000 interviews. Some of the world’s most famous people have joined her on the couch of The Oprah Winfrey Show. There have been plenty of surprising and unforgettable instances involving presidents, Hollywood greats, and everything in between.

Here are seven of Oprah’s most famous interviews over the years.

7. Sarah Ferguson, Duchess of York

Sarah Ferguson, the Duchess of York, Prince Andrew’s previous wife, has been interviewed by Oprah several times. Her most famous appearance was on The Oprah Winfrey Show in 1996, the year of her divorce, in which she discussed the breakdown of her marriage and criticized the British media, calling them “intrusive” and “cruel.”

6. Whitney Houston

Oprah sat down with Whitney Houston in 2009 for one of her most stunning interviews to date. The singer opened up about her 14-year marriage to Bobby Brown, including allegations of infidelity and emotional and physical violence. She also discussed her battles with addiction.

5. Rihanna

Rihanna gave Oprah a tour of her native neighborhood in Barbados for Oprah’s Next Chapter in 2012, before sitting down for a lengthy interview in which she detailed the brutality she faced at the hands of her former lover, R&B star Chris Brown.

4. Lance Armstrong

Lance Armstrong officially admitted to using performance-enhancing substances in bicycle competitions in 2013, after years of denial. He did a candid interview with Oprah, in which he addressed the subject for the first time on camera. He admitted to using the substances to win all seven Tour de France titles, claiming that it would have been difficult to win without them because doping was so common in the sport at the time.

3. Tom Cruise

When Tom Cruise famously climbed onto the couch to confess his love for then-girlfriend Katie Holmes on The Oprah Winfrey Show in 2005, it became one of the most talked-about moments in the show’s history. One of the first videos to go viral on YouTube was a frenetic, chaotic interview with Cruise, who was probably one of Hollywood’s greatest stars at the time.

2. Barack Obama

In 2011, then-US president Barack Obama and first wife Michelle Obama appeared on Oprah, making them the first sitting presidents to do so. The trio traveled to Chicago, the Obamas’ hometown, for the interview. President Barack Obama expressed his love for his wife and children, and Oprah stated that it was one of only a few times she felt frightened while interviewing one of her guests, describing it as an “out of body” experience.

1. Michael Jackson

Winfrey was personally invited to Michael Jackson’s Neverland Ranch for an interview in 1993. The Thriller star’s remarkable openness, which saw him disclose everything from his relationship with his father to his skin disorder, vitiligo, helped the interview become the most-watched in television history.

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