How Oprah Winfrey built her billion-dollar empire and became Hollywood royalty

Natasha Mwansa
·7 min read
<p>Queen O: how Oprah built her empire</p> (Getty Images)

Queen O: how Oprah built her empire

(Getty Images)

It’s difficult to imagine a living person more integral to the cultural psyche than Oprah Winfrey. If the US had a monarchy, Oprah Winfrey would be its Queen — with an endorsement from her akin to a kind of showbiz knighthood.

It only makes sense then, that when actual royalty need a platform to tell their story, they go to Oprah. Her interview with the Duke and Duchess of Sussex, which aired in the US last night, unleashed a dramatic set of bombshell revelations, this side of the pond we can watch the interview on ITV tonight at 9pm.

It’s a testament to Winfrey that the couple chose her as their consigliere when they decided at last to bare their souls. There is precedent — in 1996, shortly after she stopped being a working royal, Sarah Ferguson spoke to Oprah (and told her that royal life was no fairytale).

And so, ahead of tonight’s big interview with the Sussexes, we track the rise and reign of the philanthropist, author, actress, television producer and author who rules Hollywood Hills from on high.

A duchess dishes: Sarah Ferguson’s appearance on Oprah in 1996AP
A duchess dishes: Sarah Ferguson’s appearance on Oprah in 1996AP

Becoming Oprah

Born in Mississippi in 1954, Oprah Gail Winfrey first entered the public eye as the youngest and first black female news anchor at Nashville’s WLAC-TV. From Nashville she joined Baltimore’s WJZ-TV, working lower profile positions before eventually being tapped to host Chicago’s WLS-TV morning talk show, AM Chicago.

She was a hit. So much so that it became the highest-rated talk show in Chicago. On film critic Roger Ebert’s recommendation, Oprah went on to sign a syndication deal with King World for a talk show which would later become The Oprah Winfrey Show. The daytime show ran from 1986 to 2011 and garnered her a wealth of accolades, including 18 Emmys, and averaged 20 million viewers a day at its height.

The final season of the show aired in 2011 — a natural departure for the talk show host who was quoted in a Vogue interview as saying, “I never want to stay too long in the ring so I end up punch-drunk. I didn’t want people saying, ‘She shoulda quit that show three years ago!’”

Lance Armstrong on the line: One of Oprah’s famous interviewsGetty Images
Lance Armstrong on the line: One of Oprah’s famous interviewsGetty Images

She has also acted and in 1985 delivered an Oscar-nominated performance as Sofia in Steven Spielberg’s adaptation of The Color Purple. Since then she has both starred in and produced a number of acclaimed films including Ava DuVernay’s Selma, A Wrinkle in Time and Lee Daniels’ The Butler.

Then there’s her production company, Harpo Studios, which is behind Dr Phil, Super Soul Sunday and Iyanla: Fix My Life. She also has her own publication, O, The Oprah Magazine, which according to Hearst Magazines had grown to a readership of eight million as of July 2020. With the addition of her five published books (three self-help books, a food and health book, and a memoir), you get a behemothic modern media empire.

Meeting of minds: Nelson Mandela and Oprah WinfreyAP
Meeting of minds: Nelson Mandela and Oprah WinfreyAP

Money Moves and Oprah’s net worth

Oprah is worth an estimated $2.6 billion (£1.8 billion) — largely thanks to the success of her daytime talk show. She also launched the cable channel OWN in 2011 and maintains a 25.5 per cent stake in the network worth more than $65 million (£46 million), according to Forbes. She also has a seven per cent stake in Weight Watchers and is brand ambassador for the company.

As for her property portfolio? Her main residence which she calls ‘The Promised Land’ is in Montecito, California and was purchased for a cool $50 million (£35 million) in 2001. The estate includes six bedrooms and fourteen bathrooms as well as a pool, stables and vegetable gardens. In 2015, she purchased an additional 23 acres of land for $29 million (£20.5 million), bringing her total acreage in the area to almost 70 acres. High profile neighbours include none other than Harry and Meghan as well as fellow daytime A-lister Ellen DeGeneres.

She also has over $40 million-worth (£28 million) of real estate in Hawaii as well as properties in Chicago, Colorado, and an $8.2 million (£5.8 million) property on Orcas Island, off the coast of Washington State.

Magical magnetism

Spiritual gurus, politicians, drug addicts, white supremacists, Michael Jackson — name any category of person and Oprah has likely had them on her couch. “There is a kind of magic about Oprah — a connectivity that draws people to her,” wrote British Vogue editor Edward Enninful.

Women on top: Oprah with then First Lady Hillary ClintonAFP via Getty Images
Women on top: Oprah with then First Lady Hillary ClintonAFP via Getty Images

What makes Oprah Winfrey so ‘magical’ is her ability to put people at the focus of her interviews rather than subject matter. She engages with her guests openly and expressively, punctuating their insights with an animated “aha!” and often asking them to repeat profound points. You get the sense that Oprah really roots for whoever she’s speaking to, an approach comfortable enough to break down Rihanna’s bolshy exterior and build up an excitement feverish enough to have Tom Cruise jumping on couches. She extends a warmth that can melt the most recalcitrant star.

As for the “bad guys”? When people want atonement, they go to Oprah. Following his doping scandal, Lance Armstrong found himself in front of Oprah. When Lindsay Lohan wanted to overhaul her party girl image, she sought refuge in Oprah. When author James Frey was found to have fabricated parts of his best-selling memoirs, it was Oprah’s hot-seat he cowered in.

Speaking to Vogue in 2017, Winfrey said, “There’s not a human being alive who doesn’t want — in any conversation, encounter, experience with another human being — to feel like they matter.” Though careful not to pardon the wrongdoings of her guests, she at the very least offers a platform for guests to speak their truths.

Power pals: Oprah and Michelle ObamaAFP via Getty Images
Power pals: Oprah and Michelle ObamaAFP via Getty Images

Politics and philanthropy

Oprah’s power to influence public opinion on everything from presidential candidates to book sales has been dubbed ‘The Oprah Effect’. Take Oprah’s Book Club, which is said to have been influential enough to send each selection straight to the best-seller list, including Leo Tolstoy’s Anna Karenina and four books from Toni Morrison, including Paradise and Sula.

Her endorsement of Barack Obama during his 2008 presidential campaign was said to have been so successful that without it, Obama may not have made it into the Oval Office. Though she took more of a backseat in subsequent elections, telling The Hollywood Reporter she was “quietly figuring out where I’m going to use my voice in support,” Joe Biden and Kamala Harris also appeared on Oprah’s platforms before winning the 2020 presidential election.

Could she be eyeing up the White House herself in the future? Most likely not — Winfrey has previously shot down rumours of any desire to run for president, telling InStyle magazine, “I’ve always felt very secure and confident with myself in knowing what I could do and what I could not. It’s not something that interests me. I don’t have the DNA for it.” Nevertheless, if she were to run, a landslide victory would be unsurprising considering her clout — and broad appeal across the disunited States of America.

She is also an ultra-philanthropist, who has donated millions of dollars to various charities including the Clinton Foundation, the Born This Way Foundation and Women for Women International. In the past year she’s also given $10 million (£7 million) to coronavirus relief efforts, as well as a venture to help Americans access food during the pandemic.

Hold Stedy: Oprah and life-long partner Stedman GrahamGetty Images
Hold Stedy: Oprah and life-long partner Stedman GrahamGetty Images

She founded the Angel Network in 1998 — since dissolved — which raised $11 million (£7.8 million) for people affected by Hurricane Katrina. Her Oprah Winfrey Foundation supports organizations that serve children, families, and communities, with a focus on youth education, and The Oprah Winfrey Operating Foundation was founded in 2007 to support education and career development for young girls in South Africa.

Lovers and friends

Fellow media heavyweights like Gayle King, Tyler Perry and Ava DuVernay count themselves as part of Oprah’s posse as well as the Obamas, spiritual guru Deepak Chopra and the late Maya Angelou.

Though unmarried, Oprah has been in a long-term relationship with Stedman Graham, an educator on identity leadership, author and speaker, since 1986.

In an essay published in O Magazine, Winfrey wrote, “I realised I didn’t actually want a marriage. I wanted to be asked. I wanted to know he felt I was worthy of being his missus, but I didn’t want the sacrifices, the compromises, the day-in-day-out commitment required to make a marriage work. My life with the show was my priority, and we both knew it.”

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