The 10 Best Oprah Interviews That Were Even More Shocking Than Meghan & Harry's

On the night of March 7, the world let out a collective gasp as Meghan Markle and Prince Harry detailed their royal struggles in a tell-all interview with Oprah Winfrey. It was riddled with bombshell reveals, from Markle’s mental health struggles to general concerns about baby Archie’s skin tone. And while this interview will certainly go down in history as one that shook the British royal family, it’s not the only time that Oprah has delivered an explosive interview.

As we’ve seen throughout the years, the legendary talk show host has a knack for getting even the most private celebrities to open up—which explains why she’s gotten quite a few jaw-dropping confessions. From Lance Armstrong to Michael Jackson, keep reading for 10 of the best Oprah interviews.

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1. Sarah Ferguson

Meghan and Harry aren’t the only royals who sat down with Oprah for a tell-all interview. Back in 1996, Fergie met with the host to promote her memoir, My Story: The Duchess of York, and she didn't hold back while discussing her life as a Windsor. The duchess went into detail about her bribery scandal, her less glamorous life behind palace walls and her relationship with Princess Diana.

2. Rihanna

Three years after Chris Brown made headlines for assaulting his then-girlfriend, Rihanna, the pop star had an emotional interview with Oprah in 2012, breaking down into tears as she spoke about the incident and shared why she chose to forgive her “first love.” The “Umbrella” singer also opened up about her childhood, her family and how she’d been dealing with fame.

3. Kim Kardashian

Another story that made headlines in 2012 was Kardashian’s candid interview with Oprah. Not only did she address the popular rumor about her sex tape making her famous, but she also discussed whether her 10-week marriage to Kris Humphries was a publicity stunt.

4. Ellen Degeneres

Remember that landmark 1997 episode of Ellen, when DeGeneres’s character, Ellen Morgan, came out as a lesbian? In that same year, the actress and comedian made history in her groundbreaking coming out interview with Oprah, which was watched by a record 42 million people. She also revealed the heartbreaking reactions of her parents at the time and how she tried to cope with the overwhelming backlash.

5. Michael Jackson

Although the King of Pop steered clear of all interviews for more than a decade, he made an exception for Oprah in 1993—and without having any knowledge of her questions beforehand. At his Neverland home, the two discussed several sensitive topics, from his troubled relationship with his father to his plastic surgery. The revealing special turned out to be the most-watched interview in television history.

6. Janet Jackson

The pop icon’s sister, Janet Jackson, gave her only interview after the halftime show controversy at the 2004 Super Bowl. She gets vulnerable while discussing how she received all the backlash and was forced to apologize after Justin Timberlake tore off too much of her costume, exposing part of her chest to millions during their live performance.

7. Whitney Houston

The iconic songstress had been tight-lipped about her personal life for several years. That is, until she sat down with Oprah for an intimate chat in 2009. No stone was left unturned in the lengthy interview, where Houston discussed topics like her drug addiction, her time in rehab and her toxic relationship with singer Bobby Brown.

8. Mike Tyson

The heavyweight champion gave fans a rare glimpse at the man behind the tough persona in this eye-opening interview. He talks honestly about his issues with anger, his time in prison and his infamous boxing match—where onlookers saw him bite his opponent Evander Holyfield's ear.

9. Lance Armstrong

For the first time ever, the disgraced cyclist openly admitted to using performance-enhancing drugs to win all seven of his Tour de France titles, adding that it would've been impossible for him to win without them. In the 2013 interview, he also addressed accusations about his bullying and forcing other teammates to cheat.

10. Tom Cruise

Who can forget the iconic (and cringeworthy) interview where an erratic Tom Cruise treated Oprah’s couch like a giant trampoline? In the 2005 special, the talk show host attempted to chat with the actor about his new relationship with Katie Holmes, but it wasn’t exactly smooth sailing. As Oprah so eloquently put it at the time, "He's gone. The boy is gone."

nakeisha campbell bio
Nakeisha Campbell

Associate Editor, News and Entertainment

Nakeisha has been interviewing celebrities and covering all things entertainment for over 8 years, but she has also written on a wide range of topics, like career...
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