Five Of Oprah’s Best Interviews Ever

While we wait for the Harry-Meghan slot, join us on a run down of Oprah Winfrey's most legendary interview(ee)s


by Emily Watkins |
Updated on

Oprah is Oprah. What I mean is, there’s almost no one to compare her too – one of those rare human beings who goes by just one name (though of course we all know her second, Winfrey), she shares that category with the likes of Caesar, Shakespeare, Churchill. Cher.

Having crafted a career and identity in seemingly perfect harmony, Oprah is synonymous with ground-breaking interviews which get to the heart of celebrities who otherwise feel remote or untouchable. As such, it’s perhaps no surprise that Meghan Markle and Prince Harry have granted her an exclusive interview following their exit from the royal family – while you await that video with baited breath, why not revisit some of Oprah’s most extraordinary conversations from years gone by? Go on, they're all right here! Yes, here!

1. Tom Cruise, 2005

Tom Cruise’s couch-jumping appearance on The Oprah Winfrey Show has gone down in weird-celeb history. In the context of the episode, it’s a move less strange than the endlessly shared clips and GIFs made it seem in the show’s aftermath – nonetheless, Cruise’s ecstatic air, boisterous energy and proclamation ‘I’m in love!’ of then girlfriend Katie Holmes, remains quite the statment, however you look at it.

2. Whitney Houston, 2009

Shifting gears in a big way from Tom Cruise and his loved-up hypefest, Oprah’s two-part interview with Whitney Houston is a truly hypnotising exchange between two women speaking openly about pain. Whitney talks earnestly, heartbreakingly, about her abusive relationship with Bobby Brown and the jealous misogyny that lay at its core: ‘I think somewhere inside, something happens to a man when a woman has that much control or has that much fame’, Whitney muses. ‘He has to have his own’. It's one urgently eloquent moment in an interview brimming with disarming shorthands for trauma: ‘I know exactly what you’re saying – he has to have his own’, says Oprah, speaking for many women who share her recognition of what Whitney's describing, fame or otherwise.

3. Maya Angelou, 2013

You couldn’t say Oprah didn’t draw in the big names, could you? In 2013, she sat down with none other than Maya Angelou. Whether or not the SuperSoul Sunday framework is to your tastes, I think it would take a superhuman feat of stoniness not to be touched by some of Dr. Angelou’s words on love: ‘it may be the energy that keeps the stars in the firmament, I’m not sure. It may be the energy that keeps the bloody flowing smoothly through our veins, I’m not sure.’ (Hey, maybe Maya should have been a poet?)

4. RuPaul Charles, 1995 and 2018

Be still my beating heart. Part of what is so thrilling about watching RuPaul being interviewed by Oprah, at least for devotees of his like me, is the cheerful suspicion that he totally adores her – besides frequent homages on Drag Race, the protagonist of his 2020 show AJ and the Queen is totally in Oprah’s thrall, rewatching old VHS tapes of her shows in the back of his rundown RV. RuPaul said in interview with the New York Post that, like Robert, ‘I’ve used the light of Oprah Winfrey at times in my own life’ – of course, his appearances on her show are as packed with light as anyone could dare to hope.

Ru first featured back in 1995 (‘bad weather always passes over. If you could just wait it out, it will pass’) and in his latest interview, 2018, he explains what it is about drag that’s resonated so profoundly in recent years: ‘There’s a new breed of young people out there. There’s a new voice’, he says. ‘We do a convention called Drag Con […] and the kids who come don’t identify as gay or straight, and they are looking for a voice – almost a belief system that transcends the 20th century, that is completely of the 21st century’.

5. Barack Obama, 2020

Oh, who are you talking to today, Oprah? No big deal, just literally Barack Literal Obama. Filmed last year (with some very clever greenscreen technology to get around the pesky pandemic) the interview takes place in the immediate aftermath of the 2020 election. Obama is characteristically eloquent about his successor, and positive about new president and old friend Joe Biden – ‘[Biden and Harris will] re-establish […] that there’s an expectation that the president doesn’t routinely lie, or reshape the truth to his own convenience. He doesn’t call journalists enemies of the state. Those kind of things.’ Yeah, those things sound good.

READ MORE: From Fergie On Oprah To Prince Andrew On Newsnight: The Other Royal Tell-All Interviews

As The Duke And Duchess Of Sussex Announce Their Oprah Interview, How Can You Watch It?

Just so you know, whilst we may receive a commission or other compensation from the links on this website, we never allow this to influence product selections - read why you should trust us