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Caroline Overington: What it’s like to interview Oprah Winfrey

As Oprah Winfrey fronts The Weekly's October issue, Caroline Overington writes what it's like to interview to the talk show queen.

What’s it like to interview Oprah Winfrey? Well, I’m not going to lie to you. It’s pretty special.

Let me start by saying that as a general rule, interviews with very famous people can be a bit weird and stagy. They usually take place in hotel rooms. You go into the room and they’ll already be there, maybe sitting in an armchair, looking very tired.

The lights will be dimmed, and there will be hotel-style flowers on the pretty side tables, and soft music will be playing. You sit and talk for 20 or 30 minutes, and you rarely get a heart-to-heart. There’s just no time, and anyway, they’re not there to get to know you. They’re there to promote a film, a song, a book, a charity, or else they’re being paid to be there. Or they’re running for office.

It’s hard to get anything real.

There are exceptions, and apparently Tom Cruise is one. I’ve never met him, but my colleague, Bryce Corbett, has interviewed him, and he says that Tom Cruise wants to convert every single person on earth to the Church of Tom Cruise.

He’s 100 per cent present in the room. So bright is his light, he’s often all you can see.

Bill Clinton is the same. He has just buckets of charm, which you need when you’re trying to get 40 million people out of bed to vote for you in a country where they don’t even have to do the getting out of bed bit.

Just for the record, Hillary hasn’t got that X-factor. She comes across as a tiny little bit cold. People say it’s because she hates the press. She can’t afford to hate the press.

Anyway, it’s frustrating, because by and large, when people ask you, ‘Okay, so who is the most impressive person you ever interviewed?’ you just know they want you to say, oh, Barack Obama, or Muhammad Ali, or some megawatt star like Angelina Jolie.

The truth is, the best – by which I mean, the most sincere and human exchanges – don’t take place with people from politics, or from movies or TV.

The most impressive people on earth – in my opinion, anyway – are those ordinary folk who suddenly and inexplicably and unfairly find themselves caught in a tragedy of near-unfathomable proportions.

I’m thinking now about people like the Denise and Bruce Morcombes of this world; I’m thinking of Turia Pitt and Rosie Batty and Walter Mikac (whose daughters were killed at Port Arthur); plus I’m thinking of the police officers and especially the nurses who have to deal with the trauma when something goes terribly wrong.

Meeting people like that honestly makes you question yourself: could I be that strong? Could I hold it together like that? Would I be leaning in and helping others or would I be a crumpled mess on the floor? Meeting people like that makes you want to be a better person. A better parent. A better neighbour. A better friend.

I can’t say a movie star ever made me feel like that.

But anyway back to Oprah. What’s she like?

Well, the interview took place at Oprah’s OWN headquarters in Hollywood. OWN stands for the Oprah Winfrey Network. It used to be based in Chicago but now she’s making big movies – including Selma, which was nominated for an Academy Award for Best Picture – it makes sense to be in Hollywood.

It was a hot day, but it’s pretty much always hot in Hollywood, and the palm trees – like Dr Seuss palms, with long skinny trunks and a tuft of hair on top – were swaying.

There was security at the boom gate, and again when I got inside the building, but it wasn’t oppressive. Mostly: What’s your name? Who are you with? That kind of thing.

There were big fat sofas in the foyer, and coffee machines, and baskets overflowing with snacks, and a flat screen bigger than your car showing programs from the OWN network.

From memory, everything was beige or white or mirrored and everything else – the floor, the walls, the elevators – was silent and smooth.

Oprah’s communications director Chelsea came down to say hello. We went up to the floor where Oprah keeps a corner office. She was running a touch late so I sank down into yet another crazily soft, pale and tasselled sofa with Chelsea, and we talked about what we could see out the picture windows, which was Oprah’s own movie-making lot.

She loves making movies. She wants to be in more movies. She should be in more. She’s very good. Remember The Color Purple? No disrespect to Anjelica Huston, but they should have given Oprah an Oscar for that.

Ten minutes of chit-chat, and it was time to walk the corridor to Oprah’s office. The walls were lined with glossy photographs of Oprah. We stopped by the reception desk outside Oprah’s office. There was a gorgeous girl sitting there with one of those fancy head-set things on, and I expected to be ushered in, but what happened instead was: Oprah came out. And she had no shoes on. She was barefoot, but with a white pedicure. White is bang on trend for toes in Hollywood.

She made a big too-do about Australia. She loves Australia. LOVES Australians. LOVES.

We went into her office and it was enormous. ENORMOUS. Or, as Oprah might say, it’s E -N O R – M O U S – enormous! Just enormous!

There was an L-shaped sofa that was longer down one side than your whole lounge room. I sat down at one end of it, and Oprah took an armchair. She was so far away, I had to get up and move three meters along the sofa to get close enough to really see her.

She’s beautiful. Has she had work done? I don’t know. I can’t exactly see her denying it. I didn’t want to waste a question asking because honestly who cares? But she’s beautiful. Luminous skin. Clear eyes. Thick, glossy hair. Casually dressed in blue jeans and a black jumper.

We talked for 40 minutes. She leans in when she talks. She concentrates. You get the feeling she’s paying attention. Really paying attention. She repeats your question back to you and pauses like she wants to be sure she’s giving you an honest answer.

What did we talk about? Love and life and loss; regrets and sorrows and power and pain and human beings, and how confounding and mysterious is the universe. What it means to be happy. What it means to be good. (You have to get The Weekly to read the whole interview; she’s on the cover.)

She seemed to really like my questions. A couple of times, she actually said: Wow, good question! So, when time came to leave, I was thinking: okay, I think I did pretty well. In fact, I’d go so far as to say I think we got on great!

It left me on this strange high, thinking: I sat down with Oprah and we got on great.

I guess it took about an hour for the truth of the matter to dawn, which is that everyone who meets Oprah ends up feeling good about themselves. Because that’s her gift. Oprah has the gift of making you feel special. Like what you said mattered.

In days gone by – in a time before television – she would have been a guru of some kind, like a Bhagwan, because Oprah is quite simply the kind of person that other people want to follow down the street.

Whatever that thing – that magic thing – is that some people have that makes you like them, she has it. Bill Clinton has it, Nelson Mandela had it, Hugh Jackman has it, a handful of people across the globe have it, and she’s one of them, and when you see that power in action, it’s astounding.

So, there’s your answer. She’s OPRAHHHH! She’s quite simply mesmerizing, and if you don’t believe me, why not go see her for yourself?

Here’s a link to her tour. She’ll be here in December:

Wednesday, December 2: Melbourne – Rod Laver Arena

Friday, December 4: Adelaide – Adelaide Entertainment Centre


Monday, December 7: Perth – Perth Arena

Thursday, December 10: Brisbane – Brisbane Entertainment Centre

Saturday, December 12: Sydney – Sydney Allphones Arena

Listen to Caroline talking to Brisbane’s 97.3 FM about meeting Oprah here.

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