How Gwyneth told friends Brad Pitt is ‘dumber than a sack of s***’ and ‘has terrible taste in women’. Bombshell new book reveals truth behind star’s perfect facade – and dark underbelly of Hollywood relationships. Read it only here

In the autumn of 1994 Gwyneth Paltrow was offered two film roles. The first was the chance to play the wife of Brad Pitt, then at the height of his fame, in the thriller Se7en.

But shortly before she agreed to take the part, Gwyneth was also asked to star opposite Keanu Reeves in the crime comedy Feeling Minnesota. Undecided, she asked a friend for advice.

‘Well, who do you want to date?’ said the friend. ‘Brad Pitt or Keanu Reeves?’

Gwyneth chose Brad Pitt.

The relationship between the two, which would dominate the media for years, came quickly to fruition. Soon the couple were holding hands on set and leaning on each other, and smoking cigarettes together outside their trailers.

‘I don’t think she was in awe of his fame. I think she just liked him,’ remembers the film’s costume designer Michael Kaplan. ‘If they didn’t get together, it would’ve been a surprise. I think it was kind of love at first sight.’

Gwyneth’s father Bruce Paltrow, however, WAS in awe. After visiting the set, he said to one friend: ‘Can you believe my daughter? Oh my God. It’s f***ng Brad Pitt!’

Gwyneth Paltrow has been admired and envied by a massive global audience for three decades. Love her or hate her, we haven’t been able to look away.

Born to a successful television producer and a Tony Award-winning actress, Bruce Paltrow and Blythe Danner, Gwyneth seemed destined for fame from an early age. She attended elite private schools in New York and Los Angeles and was adored by her parents’ famous friends, among them her godfather Steven Spielberg.

Bruce and Blythe guided their firstborn to play bit parts in Chekhov plays and Greek tragedies as a child. They then steered her toward well-written, tasteful roles in her late teens. Nothing, it seemed, could stand in her way – and nor did it.

As the world knows, an enviable acting career soon followed – along with an Oscar for the 1998 Shakespeare In Love – and serious relationships with some of the world’s most famous men. Gwyneth then channelled her notoriety into her own lifestyle brand, Goop.

But although her perceived relatability would be crucial to her success, she hadn’t really lived a day as a ‘normal’ person. It wasn’t that Gwyneth didn’t try to understand average people. She simply had no point of entry into their lives. To her, they were always more like a theoretical construct.

Her regular pronouncements about poverty, obesity, divorce and nutrition revealed just how little she had in common with the masses, and have helped make Bruce and Blythe’s golden child one of the most polarising celebrities in the world.

That dual and complex fascination – hating Gwyneth and at the same time wanting to be her – has persisted ever since.

By the time filming began for Se7en, Brad Pitt was a global movie star who had a habit of falling in love with his co-stars – among them Geena Davis in Thelma & Louise.

All the privileges that had defined Gwyneth’s childhood – wealth, famous parents, private schools, Hollywood connections – were foreign to Pitt.

He had grown up in Missouri and was raised as a Southern Baptist by a father who owned a trucking company and a mother who worked as a school counsellor. Two weeks shy of earning a journalism degree at the University of Missouri, Pitt headed to Los Angeles to pursue acting.

Once there, he took odd jobs, including dressing up as a chicken for the chain restaurant El Pollo Loco. He had small roles on shows like Dallas and Growing Pains before landing his big break in Thelma & Louise. During the filming of Se7en, People magazine crowned him the ‘Sexiest Man Alive’.

Gwyneth hadn’t given Brad much consideration before then. ‘I thought he was very handsome from movies – you know, the way people are. But I also thought, Oh, he’ll just be one of those young Movie Star Boys. But he’s not. He’s a really good person. And I knew it that first day on the set.’

When filming ended Gwyneth and Pitt took a ten-day trip to St Barts, where they rented a private villa. Here, they didn’t have the same security protection they’d had on set, and they were photographed completely nude in broad daylight outside the property.

The villa was ‘in full view of a well-used footpath to the nearby beach’, according to a British tabloid newspaper that printed the photos on April 30, 1995. The images ran again a week later in the US National Enquirer, this time with strategic blurring.

After the photos came out, Madonna, who had once written to Bruce years before with a personal note telling Gwyneth to stop smoking, stepped up once again.

‘She’s experiencing the upsides and the downsides of being famous for the first time,’ she said. ‘That’s a lot for someone to take. So, I’m happy to help her.’

The two began a friendship that would last for well over a decade before ending abruptly during Gwyneth’s relationship with Coldplay front man Chris Martin (more of which tomorrow).

Gwyneth’s transition from working actress to A-lister coincided with her arrival at Miramax Films, the company owned by Harvey Weinstein. He had a reputation for making quality movies. He was also known as a mercurial bully.

Gwyneth would later recall meeting Weinstein in the mid-1990s at the Toronto Film Festival, when he stopped her to praise her work. She said she felt ‘legitimised by his opinion’.

In 1995, he offered her the part of Emma in an adaptation of the Jane Austen novel of the same name, the movie that would make her a star. For Weinstein, it was his opportunity both to hitch her to Miramax and to develop his own relationship with her.

‘He was in love with Gwyneth,’ Miramax producer Paul Webster would later say. ‘He thought of her as his next protege and was in his star-making mode.’

Gwyneth saw Weinstein initially as a mentor. She had been charmed and flattered by their encounter in Toronto. Now here he was, giving her the lead part in a movie specifically to make her as famous as she’d always known she’d be. But Weinstein soon revealed his true nature to her.

Before filming started, Gwyneth was told by her agent to meet him in his rooms at the Peninsula Beverly Hills hotel. She duly did so, understanding the location to be for privacy. ‘I bounced up there, I’m sort of like a golden retriever, all happy to see Harvey,’ she later recalled.

Toward the end of an otherwise fine, business-centred conversation, the dynamic changed. Weinstein, then around 43, put his hands on her, and suggested they move to the bedroom to give each other massages.

‘I was a kid. I was signed up. I was petrified,’ she later told The New York Times. Weinstein asked again to go to the bedroom.

Gwyneth found a way to excuse herself without offending her new boss. She told her agent and a handful of close friends and family, including Pitt, what had happened.

In New York on May 2, 1995, a few months before filming on Emma started, Pitt and Gwyneth attended the Broadway opening night of Hamlet, starring Ralph Fiennes.

Pitt knew how terrified Gwyneth had been after her encounter with her boss. He also knew she had signed on to do two movies for him. He decided to approach Weinstein, also a guest at the premiere.

‘At that moment, I was just a boy from the Ozarks on the playground… and that’s how we confronted with things,’ he recalled. He told Weinstein something to the effect of ‘If you ever make her feel uncomfortable again, I’ll kill you.’

Pitt returned to Gwyneth’s side and told her what he had said. She would go on to describe it as Pitt ‘energetically’ throwing Weinstein against the wall. ‘He leveraged his fame and power to protect me at a time when I didn’t have fame or power yet,’ she said.

After the confrontation Weinstein called Gwyneth. He screamed at her for what she would later remember as ‘a long time’, threatening to ruin her career. She told The New York Times that she feared she would lose the part in Emma and asked that their relationship remain professional.

Weinstein disputed her version of events. In an email, he admitted to asking Gwyneth for a massage and said that he apologised to her. He also claimed that he never threatened her after Pitt confronted him, and that he apologised to Pitt.

He believed Gwyneth forgave him for ‘making a pass at her’, explaining: ‘We could never have had the working relationship and friendship we had if she hadn’t forgiven me.’

That summer Brad accompanied Gwyneth to London for the filming of Emma. He had a backpack, and she had around five suitcases.

Had she travelled alone, the studio would have given her the same modest accommodation as the rest of the cast and crew. But Brad and Gwyneth together needed cover.

For part of the shoot, they were booked into a suite at the five-star Berkeley Hotel in Knightsbridge. Film bosses ensured that the hotel made special arrangements for Pitt, allowing him to dine in a T-shirt although gentlemen were required to wear jackets.

But despite outward appearances, cracks in the relationship were starting to show. During filming Gwyneth expressed doubts to one crew member that Pitt was right for her, and admitted that she had a crush on Hugh Grant.

She perceived herself as an Upper East Side girl with a fancy private-school education who’d grown up around Wall Street families, while he was a boy from Missouri born to religious, conservative parents. Pitt had attended church each week as a kid and been baptised at around nine.

‘Brad and I had very different upbringings,’ she told an interviewer. ‘So when we go to restaurants and order caviar, I have to say to Brad, “This is Beluga and this is Oscietra”.’

Then there was Pitt’s habitual tardiness, which drove Gwyneth — who was always punctual — crazy.

In addition, some of Gwyneth’s closest friends didn’t think she and Pitt were right for each other.

Pitt had spent his high school years going to Christian revivals where he’d ‘be moved by the Holy Spirit,’ he later said, while rock concerts were frowned upon.

Pitt started questioning his faith in college and declared himself an atheist, but Gwyneth could not relate to his family’s Christian devotion and poked fun at it with her friends.

The main thing she seemed to have in common with him was fame, which didn’t seem to those close to her like enough to hold a relationship together.

In March 1997 Gwyneth’s former classmate Caroline Doyle, the editor-in-chief of Russian Marie Claire, convinced her to attend a launch event for the magazine in Moscow. In a huge publicity coup for the magazine, Pitt joined her. Pitt was well known in Russia; Gwyneth was not.

They played the happy couple for onlookers. Gwyneth seemed ‘domesticated’ with Pitt, one friend said. She would cook dinners at home and make plans for them to do things as a couple.

But she would also go to designer showrooms to pick out clothes, and Pitt would say things like: ‘Do you really think you should wear that? Don’t you think that’s too sheer?’

Gwyneth was a star, and her life was becoming a series of perks. Shipments of free designer handbags and clothes started arriving at the town house she had recently moved into with Pitt.

She got free tickets for friends to fly on Concorde and a free stay at a top hotel’s presidential suite in Paris. When she went out to dinner, someone in the room would pick up the bill. The need for bodyguards became more frequent.

Underneath it all, the strains in her 18-month relationship with Brad Pitt were preoccupying her. After Emma came out, Gwyneth went over to makeup artist Kevyn Aucoin’s Manhattan apartment and cried about Pitt multiple times, tucked into the couch in the cavernous living room.

What she described seemed to Aucoin, according to someone with knowledge of his thinking, like Pitt might be verbally and emotionally abusive. He wanted to be with her but seemed to feel threatened by her success and all the attention she received.

Aucoin sensed that she was afraid to lose the leverage and security that came with being Pitt’s partner, and the public power of their relationship was muddled in her mind with the private experience of it.

His advice to Gwyneth was always frank, said someone close to him at the time: ‘You really need to end this.’

At the end of 1996 Gwyneth flew on a private plane to Argentina, where Pitt was filming Seven Years In Tibet.

One day he surprised her on the balcony of his rented house with a marriage proposal and a diamond engagement ring he had designed himself. They had been dating for two years. Gwyneth was 24 and Pitt 33.

Gwyneth’s friends for the most part thought Pitt was a really good guy and viewed her as a really good girlfriend to him. But they were still surprised that she said yes. While the relationship had momentum in the press, the two still seemed to have little in common. It was not to last much longer.

The public story of their breakup six months later focused on Pitt’s happiness: according to one report, he resented that Gwyneth was reining in his partying; another claimed that he was ‘burnt out’; and yet another alleged that Gwyneth had called off the wedding because Pitt was ‘nervous about such a serious commitment’.

What went mostly unacknowledged was that Gwyneth had valid reservations, but not about Pitt’s partying. Gwyneth and Pitt never publicly gave a concrete reason for their breakup, though two people recalled a rumour about it stemming from Gwyneth cheating on Pitt while she was filming the romcom Sliding Doors.

In her 2018 profile of Gwyneth for The New York Times Magazine, Taffy Brodesser-Akner claimed: ‘I heard that she had an affair with her Sliding Doors co-star John Hannah when she was with Brad Pitt.’

Asked about it the next year in Vanity Fair, Pitt dodged: ‘Isn’t it true of a lot of people? Since you started dating, there’s always been that period until you find the one you want to go the distance with?’

‘But you thought you had found the one,’ writer Cathy Horyn said. Pitt then looked away: ‘But I was wrong. You figure it out.’

In later interviews, Gwyneth blamed herself. In 2017, she said: ‘I f****d that up, Brad!’

‘I definitely fell in love with him,’ she told broadcaster Howard Stern in 2015. ‘He was so gorgeous and sweet. I mean, he was Brad Pitt! My father was devastated [when we broke up].

‘My father loved him like a son. I was such a kid. I was 22 when we met. It’s taken me until 40 to get my head out of my ass. You can’t make that decision when you’re 22 years old. I wasn’t ready, and he was too good for me.’

In August 2000, a reporter asked her how she felt about Brad Pitt marrying Jennifer Aniston the previous month. ‘Are you really asking me this question?’ Gwyneth replied, her eyes reportedly ‘daggers’. ‘I can’t comment on this kind of thing.’

In reality, Gwyneth confided to friends that she’d felt sad when she learned they were getting married. She was also fond of telling them that Brad ‘has terrible taste in women’.

Several years after her break-up from Pitt, Gwyneth became one of the faces of Estee Lauder, forming a cordial relationship with the founder’s granddaughter Aerin Lauder.

At one dinner, the two were talking about Pitt. According to someone who heard the discussion, Gwyneth allegedly told her: ‘He’s dumber than a sack of s***.’

While Gwyneth was reported to have met 26-year-old Ben Affleck in late 1998 at a dinner hosted by Harvey Weinstein, she had in fact met him the previous year during a Miramax press day for the film Good Will Hunting, which Affleck starred in alongside Matt Damon.

Affleck’s background was much more similar to Gwyneth’s than Brad Pitt’s. He was raised in Cambridge, Massachusetts, and his mother had attended a school on the Upper East Side, not far from Gwyneth’s alma mater Spence, and then Harvard. His father was a playwright and alcoholic who moved out when he was young.

Affleck himself was struggling with alcoholism and a gambling habit around the time he met Gwyneth. And while he was a better match for her intellectually, her friends had reservations about him, largely because of his addiction issues but also because he didn’t always seem to reciprocate her affection.

He was working out how to manage his newfound fame and had a group of mates he liked to hang out with. Her friends felt he at times seemed more interested in playing video games with the guys at his house than being with Gwyneth.

Though Affleck was not able to give her the same commitment and attentiveness she showed him, Gwyneth might have had a difficult time giving up their physical chemistry.

She spoke openly about how much she enjoyed their sex life – it was the ribald side of her that her friends knew well but that the public didn’t see.

She told Kevyn Aucoin that she loved it when Affleck performed a particular sex act on her: ‘I’m a very sexual person,’ she told Harper’s Bazaar in 2001.

In 2024, she went on the Call Her Daddy podcast and told host Alex Cooper that Ben was a ‘technically excellent’ lover.

But her relationship with Affleck began to deteriorate within only a few months. Her friends worried that when she prepared elaborate dinners for him, he would just decide to go out with his friends.

When Affleck was in Savannah, Georgia, to film Forces Of Nature alongside Sandra Bullock, the New York Daily News reported, ‘[S]pies say that while the couple is apart, Affleck has acquainted himself with one of the local beauties. ‘Tis said that the woman regularly stops by Affleck’s house and that the duo has been using his back-yard pool and not just for swimming.’ One of his friends denied anything was amiss with Gwyneth.

Gwyneth and Affleck broke up the next month. Even the intellectual attraction and their physical chemistry couldn’t overcome his self-destructive impulses, which may have even included cheating on her, according to one friend from the time.

After the end of the relationship, Gwyneth said: ‘I love men, even though they’re lying, cheating scumbags.’

BOOK CREDIT Adapted from Gwyneth by Amy Odell (Atlantic Books, £20), to be published July 31. © Amy Odell 2025. To order a copy for £18 (offer valid to 09/08/25; UK P&P free on orders over £25) go tomailshop.co.uk/books or call 020 3176 2937. 

TOMORROW Consciously uncoupling from Chris Martin – and Madonna.