Oprah Winfrey’s Top 5 Most-Watched Interviews so Far, Though That Could Change Soon

Oprah Winfrey made a name for herself as one of the most influential and prominent producers and television hosts of the past few decades. Her show and subsequent interviews will be remembered for a long time and she’s had some of the most hard-hitting and eye-opening specials. It’s no surprise that Prince Harry and Meghan, Duchess of Sussex’s first on-screen interview since leaving the royal family will be with her on March 7. 

That interview, in particular, is causing a lot of stir and will most likely go down in history as one of her more notable interviews. But until then, which interviews are Oprah’s most-watched on YouTube? Experts from OnBuy.com reported Winfrey’s most-watched interviews, based on YouTube views available on the site. The top five might be surprising. 

5. Ellen Degeneres

Coming in fifth place is the 2017 conversation between Oprah and Ellen Degeneres. It has around 5.2 million views at the time of reporting and it’s the 20th anniversary of Degeneres’ coming-out episode of her show in 1997. When she did that episode, it was a big deal at the time since being “out” as a lesbian in the ’90s was not common in mainstream media personalities. She did an interview with Winfrey, another with Diane Sawyer, and the cover of Time magazine according to Degeneres.

So in this 2017 clip, which was on Degeneres’ show but counted in this list because it was more of a conversation between the two and not a typical Ellen interview, they talk about the extreme backlash Winfrey received from having Degeneres on her show. Degeneres also talked about why it was important for her to come out and Winfrey stated why that was brave as well. 

4. 50 Cent

Coming in fourth place with almost 6 million views is Oprah’s 2012 interview with rapper 50 Cent. In this video, he recalled getting shot 9 times in front of his grandmother’s house in 2000. Like a lot of videos on this list, it’s not the full interview that was released on her show or on-air, but this part of the interview in particular is what has the most views. 

This shooting was a pretty pivotal moment in his life and, although devastating and obviously traumatic, it is talked about a lot in regards to his career. In an interview with Vanity Fair in 2013, he said that a piece of the bullet shrapnel had to stay in his tongue because it might have done more damage if they’d tried to take it out, but doing so gives him his noticeable talking — and rapping — sound today. 

3. Donald Trump

The thing about this interview, and most likely the reason it has so many views (7.2 million), is that it’s such a stark look into the future, probably more so than any of the other videos on this list. This interview took place back in 1988 when Donald Trump “teased a presidential bid” as the title says. As the world knows now, it came true.

But interestingly, the point of this video showed his criticism of the United States’ foreign policy and the lack of taxes on trade to other nations. And when Oprah asked him whether he would actually run for president in the future, since he had such “presidential” things to say, he said, “probably not.” Trump said that he didn’t have the “inclination to do it” at the time, plus Winfrey pointed out that it “doesn’t pay as well.” But he said that if the U.S. was in a situation where he saw he could step in and run, he would. 

2. Michael Jackson

With over 7.8 million views, Oprah’s interview with Michael Jackson from 1993 is her second-most-watched interview on YouTube. This was a pretty big interview and has multiple parts available on YouTube, but this video covers Jackson’s skin tone, which was a big topic of conversation. 

Winfrey asks Jackson regarding a story that previously circulated about how he wanted a white child actor to play him in a commercial. However, he was pretty defensive about it in the interview, denying that. This is when he shared that he had the skin condition vitiligo that he claimed caused his skin to lighten. She questioned him more about it, but he wanted to keep things private. At some point during their time together, Winfrey asked him what he most wanted to be remembered for, and Jackson said he, “Simply wants to be loved where” he goes.

1. Mike Tyson


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In the number 1 spot with almost 10 million views is Winfrey’s interview with Mike Tyson in 2009. She’d interviewed him previously and he talked about how he was not remorseful regarding his fight with Evander Holyfield. You know, the one where he bit off both of his ears in the infamous fight. In this video, Tyson and Holyfield are together and Tyson gives him a sincere apology.

This is definitely the shortest video on the list, but most likely the contrast between Tyson’s first interview to his last one drew a lot of attention from viewers on the internet.