As Harry Styles steps out with new lover Olivia Wilde, ALISON BOSHOFF examines her past

The One Direction star turned solo artist and actor met actress and director Olivia Wilde on the set of the forthcoming film Don’t Worry Darling

The One Direction star turned solo artist and actor met actress and director Olivia Wilde on the set of the forthcoming film Don’t Worry Darling

The ten-year age gap has drawn attention — and protests from some of his devoted fans — as Harry Styles‘s new love Olivia Wilde is 36 to his 26.

However, that’s far from the only gulf between Hollywood’s hottest new couple.

The One Direction star turned solo artist and actor met actress and director Olivia Wilde on the set of the forthcoming film Don’t Worry Darling.

Olivia has been married once — for eight years — and was also engaged to actor Jason Sudeikis, with whom she has two children, Otis, six, and Daisy, four.

By contrast, many of Harry’s romances — like the ones with pop star Taylor Swift and the late TV presenter Caroline Flack — have been relatively brief.

And, while Harry, who was brought up above a pub, left school in 2010 directly after his GCSEs, his new girlfriend is the descendant of several illustrious and interconnected English literary dynasties.

Olivia’s childhood was characterised by dinner parties at the family home in Washington DC attended by the likes of Mick Jagger, author Salman Rushdie and film-maker Stephen Spielberg.

Her British father works there as a journalist. The late writer Christopher Hitchens was her babysitter.

Her relations include Brideshead Revisited author Evelyn Waugh, the novelist Emma Tennant — half-sister of Colin Tennant, who was later Lord Glenconner — and a controversial Anglican bishop. The BBC’s former economics editor Stephanie Flanders is her cousin.

Olivia was also once married to an Italian prince, and through him is linked by marriage to the doomed Getty dynasty, as well as to the late actress Elizabeth Taylor.

Harry’s family are a shade more ordinary. He is the son of Des, who lives near Manchester and has worked in sales and marketing, and Anne, who ran a pub with her second husband and now does charity work.

Before finding fame with The X Factor, Harry had ambitions to be a florist or physiotherapist.

It’s fair to say that their early years experiences are poles apart.

Olivia has been married once — for eight years — and was also engaged to actor Jason Sudeikis, with whom she has two children, Otis, six, and Daisy, four

Olivia has been married once — for eight years — and was also engaged to actor Jason Sudeikis, with whom she has two children, Otis, six, and Daisy, four

At the age when she was ticking off Mick Jagger for sitting in ‘her’ chair at the dinner table, Harry was singing karaoke at the Elms pub in Pickmere, Cheshire, and living above the Antrobus Arms in Northwich, run by his stepfather, John Cox.

He went to the local comprehensive in Holmes Chapel and had a Saturday job at the local bakery.

By contrast, Olivia attended a private boarding school in Massachusetts that educated former U.S. presidents George H.W. Bush and George W. Bush.

Despite their very different social circles, the relationship is already said to be ‘very serious’ and he has apparently met her children.

So what is the story of Olivia Wilde’s intimidatingly successful family and what will they make of her charmingly ordinary pop star beau? 

The Daddy who is pals with Jagger 

Olivia says: 'Mick [Jagger] is a friend of my parents and once came to the house when he was touring. He was sitting in what was usually my seat at the table. I came downstairs not caring who this person was and demanded that he vacate my seat'

Olivia says: ‘Mick [Jagger] is a friend of my parents and once came to the house when he was touring. He was sitting in what was usually my seat at the table. I came downstairs not caring who this person was and demanded that he vacate my seat’

Her father is the distinguished documentary maker, author and journalist Andrew Cockburn. Born in London but brought up in County Cork, Ireland, Andrew has lived in America since 1979 with wife Leslie, who produces the news show 60 Minutes.

Andrew is the Washington editor of Harper’s magazine and has written for The New York Times and Vanity Fair. He co-produced the 1997 film The Peacemaker, starring George Clooney. 

Olivia says: ‘Because my parents were well-known journalists, our house in Washington DC was always full of artists, intellectuals and politicians.

‘We had an extraordinary long table in our dining room that was always packed with people, and my mum would make salmon for them.

‘Mick [Jagger] is a friend of my parents and once came to the house when he was touring. He was sitting in what was usually my seat at the table. I came downstairs not caring who this person was and demanded that he vacate my seat.

He just looked at me and said ‘Go to bed’ in a very sweet way. I knew from the way everyone reacted that there was something special about this guy.

‘Everyone was laughing because I demanded that Mick Jagger leave the table.’

Olivia, whose childhood summers were spent in Ireland, idolises her father — but changed her surname to Wilde in honour of Oscar Wilde and the many writers in her family.

She says: ‘It wasn’t a rejection of my name, but I wanted to establish some independence from my family name and from their work. They are very political and pick battles with different people, some of whom are very prominent in the film world, and it was very muddy for me.

‘You never know who will take things personally.’

A brother in arms with Hemingway

Olivia’s grandfather was the renowned radical British journalist Claud Cockburn.

The son of a British Consul General, Claud was an Oxford graduate, journalist on The Times and leading member of the Communist Party of Great Britain.

He wrote for the Daily Worker communist newspaper under an alias. He reported on the Spanish Civil War, and was heavily criticised as Stalinist and biased by George Orwell in his 1938 memoir Homage To Catalonia.

Olivia says: ‘I didn’t know my grandfather, Claud Cockburn, but he was an amazing journalist. He was friends with Graham Greene and fought in the Spanish Civil War with Ernest Hemingway. He died right before I was born, but it’s bizarre — everyone had such a powerful relationship with him and he was such a huge influence on the family that I always feel as though we had this really intense relationship.

‘He was definitely a huge inspiration to us all.’

The brideshead branch of family

ITV’s production of Evelyn Waugh’s Brideshead

ITV’s production of Evelyn Waugh’s Brideshead

Brideshead Revisited writer Evelyn Waugh is another relation. 

Olivia says: ‘My family are all incredible. Evelyn Waugh was my grandfather’s cousin.’ 

The novelist and Claud Cockburn share a common ancestor: Lord Cockburn, a Scottish lawyer who was the Solicitor General in Scotland from 1830 to 1834. He had five daughters and six sons.

One daughter, Catherine, married literary critic and publisher Arthur Waugh and had sons Evelyn and Alec, also a novelist.

One of his sons, Henry, had a son called Francis, who was a judge in India. Francis also had a son, whom he called Henry, and this Henry was British Consul General in India, and was Claud Cockburn’s father. 

Model for cabaret’s divine Sally Bowles

Olivia’s grandfather Claud romanced Jean Ross, the war correspondent, fashion model and cabaret singer.

Jean was the inspiration for the fictional character Sally Bowles, created by writer Christopher Isherwood in his novella of that name. It was made into a musical and then the 1972 film Cabaret, starring Liza Minnelli (below).

As a war correspondent for the Daily Express during the Spanish Civil War, Jean witnessed the siege of Madrid while pregnant with Claud’s child. He left her when their daughter Sarah was three months old — he was still married to his first wife. Within months, Claud had started a new relationship with Patricia Arbuthnot — Olivia’s grandmother — and started a family with her.

Jean later said that ‘having a man around was like having a crocodile in the bath’.

She disliked the apolitical and ‘crude’ characterisation of Sally Bowles and found it offended her principles. She died in 1973.

Jean was the inspiration for the fictional character Sally Bowles, created by writer Christopher Isherwood in his novella of that name. It was made into a musical and then the 1972 film Cabaret, starring Liza Minnelli (pictured)

Jean was the inspiration for the fictional character Sally Bowles, created by writer Christopher Isherwood in his novella of that name. It was made into a musical and then the 1972 film Cabaret, starring Liza Minnelli (pictured)

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The Italian Prince and Liz Taylor 

When she was 18, Olivia Wilde met film-maker Tao Ruspoli, an Italian prince. His father was Alessandro, known as Dado, a notorious Italian playboy in the 1950s and 1960s who was said to be the inspiration for Fellini’s classic film La Dolce Vita.

Dado married three times and counted Salvador Dali, Truman Capote and Brigitte Bardot among his friends. His full title was the 9th Principe di Cerveteri, 9th Marchese di Riano, 14th Conte di Vignanello and Prince of the Holy Roman Empire — although, as Wilde says, ‘it’s only a papal title’.

Tao was the offspring of a liaison with actress Deborah Berger, whom Dado never married.

Tao was raised in Rome and Los Angeles. He has a degree in philosophy from University of California, Berkeley.

When he met Olivia, he was living on an old school bus and they married on board the bus in 2003 after just six months together.

Olivia says: ‘I got married on a school bus in Venice Beach. We were hippies and we were living on a school bus, and it was a totally spontaneous decision.

‘At the wedding we had our two best friends and the justice of the peace. My parents found out months later, but they weren’t upset. We had a big party at their farm in Virginia and a party at Tao’s family castle in Italy as well.’

They were divorced after eight years of marriage. Olivia, who by then had landed TV roles in The OC and House and film roles in Tron and Cowboys & Angels, dumped him. 

She says: ‘The trauma of the divorce has been humbling. And for the first time, I’m a little wobbly.’

There followed rumoured flings with actors Justin Timberlake, Ryan Gosling and Bradley Cooper.

After the marriage ended, Tao said: ‘I’m in a state of total crisis. My wife has just left me after nearly ten years together and my whole world has crumbled. I’m about to lose my home, my adopted family, everything I care about.’

Through this first marriage, Olivia also has links to the Getty dynasty.

Tao’s brother Bartolomeo married Getty heiress Aileen, who found fame as one of the first publicly HIV-positive role models.

Aileen Getty, the daughter of philanthropist and oil heir Sir Paul Getty, had previously been married to Liz Taylor’s son Christopher Wilding and continued to work with Taylor to support the HIV-positive community.

Aileen and Bartolomeo are now divorced. 

Our man in the Middle East 

Olivia’s uncle is Patrick Cockburn, who is an award-winning Middle East correspondent for the Financial Times and The Independent, and also an author and commentator. He was one of the few journalists to remain in Iraq throughout the first Gulf War.

He is married to Jan Montefiore, a professor of English literature at Kent University.

She is a daughter of the late Bishop of Birmingham, Hugh Montefiore.

Hugh, from a prominent Jewish family, converted to Christianity after having a vision of Jesus while at Rugby School. 

Her cousin the economics whizz 

The BBC economics editor for five years, Stephanie Flanders is also a part of the Cockburn dynasty — she and Olivia Wilde share a grandfather.

Stephanie’s mother, Claudia Cockburn, is the daughter of Hope Cockburn, who was grandfather Claud’s first wife.

This makes Stephanie and Olivia cousins because their parents are half-siblings.

Claudia Cockburn was a disability activist who married Michael Flanders of the comedy singing duo Flanders and Swann.

Stephanie now works for the investment bank JP Morgan.

Mustique connection

She was the elder daughter of Christopher Tennant, 2nd Baron Glenconner, and his second wife, Elizabeth. Colin Tennant, who owned Mustique and was great friends with Princess Margaret (right with Colin), was Emma's half-brother

She was the elder daughter of Christopher Tennant, 2nd Baron Glenconner, and his second wife, Elizabeth. Colin Tennant, who owned Mustique and was great friends with Princess Margaret (right with Colin), was Emma’s half-brother

Olivia Wilde’s late uncle Alexander Cockburn was married to the author Emma Tennant.

She was the elder daughter of Christopher Tennant, 2nd Baron Glenconner, and his second wife, Elizabeth. Colin Tennant, who owned Mustique and was great friends with Princess Margaret (right with Colin), was Emma’s half-brother.

Alexander Cockburn, who died in 2012, emigrated to the U.S. and worked as a journalist like his brother Andrew. A socialist who later identified as an anarchist, Alexander edited the political newsletter CounterPunch and wrote for The Village Voice.

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Additional reporting: Barbara McMahon

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