di Caprio at 50: The Hollywood superstar may have finally broken Leo’s law (by dating a woman over 25), but this is why many believe his wild days won’t be over anytime soon

For most men, turning 50 is a milestone that might, perhaps, evoke fond memories of youthful indiscretions before marriage and family intervened.

But for Leonardo DiCaprio, who celebrates his half-century in eight days, there will be little time for reflecting on the ‘glory days’ of youth – because the Oscar-winning actor is still living life exactly like he did in his 20s.

While the once baby-faced star of Titanic and The Beach may be showing his age, the twentysomething women with whom he surrounds himself most certainly are not.

So notorious is the star’s habit of ditching much-younger girlfriends once they reach the age of 25, that many in Hollywood refer to it as ‘Leo’s Law’.

A producer who worked with the actor, who commands £20 million a movie, said: ‘Everyone in town jokes about ‘Leo’s Law’ because whenever you see him, he looks older but the women on his arm look exactly the same. They’re usually blonde, always great-looking and half his age. My Tupperware is older than some of his girlfriends!’

If DiCaprio’s 49th birthday is anything to go by – he is as infamous for his Great Gatsby-style partying as for the endless rotation of starlets on his arm – his 50th will be epic, even by the standards of a town used to celebrity excess.

The producer said: ‘Leo’s parties are legendary. Last year he took over a private event space in Beverly Hills and everyone from Lady Gaga to Beyonce and Jay-Z to Kim Kardashian were there.

‘Leo is usually on the sidelines, surrounded by beautiful young women, quietly watching and observing. But last year was a shocker because he got up and started rapping, which is the only time I’ve seen him put the spotlight on himself.’

DiCaprio’s official date for his 50th will be Victoria’s Secret model Vittoria Ceretti.

The pair recently celebrated their first anniversary and Vittoria, 26, is the first long-term girlfriend to break ‘Leo’s Law’ and survive his 25-year-old ‘cut off’.

His romances with the likes of Gisele Bundchen, Bar Refaeli, Blake Lively, Erin Heatherton and Nina Agdal all ended before their 25th birthdays.

Before Vittoria, he spent five years with TV actress Camila Morrone who starred in Amazon’s hit musical drama series Daisy Jones & The Six, but ditched her just weeks before she turned 25.

Then came a brief fling with model Gigi Hadid (an ‘ancient’ 27) who was rapidly followed by 23-year-old starlet Victoria Lamas, prompting her father, actor Lorenzo Lamas, to quip: ‘I told her to treat the relationship like a holiday. Enjoy it as much as you can for as long as it lasts.’

The relationship imploded after a couple of months.

DiCaprio met current girlfriend Vittoria at the Cannes Film Festival in May last year but the pair reportedly did not become serious until around 12 months ago.

The producer said: ‘He and Vittoria seem happy but she’s ‘old’ by his standards. Perhaps she’s the one who will finally get him to settle down? I doubt it.’

So why is DiCaprio seemingly unable to maintain a long-term loving relationship with a woman his own age? Some point to his unconventional childhood, blaming the ’emotional immaturity’ which occurs when a person become famous at a young age. 

Reputation manager Eric Schiffer said: ‘Leo was a child star who became a superstar with Titanic, which he filmed when he was 21 and came out when he was 23.

‘You often find people get ‘stuck’ at the age they became famous. Leo dated 23-year-olds when he became famous and he’s still dating them today. It smacks of emotional immaturity when a person cannot find deep, meaningful love with someone their own age.

‘One of life’s great joys is finding a partner you share common goals and interests with, that you can build a family with.

‘Leo seems to be stuck in an emotional time warp.’

Los Angeles marriage counsellor Molli McIlvaine goes further, describing the sight of a near-50-year-old dating much younger women as ‘cringe-inducing’.

‘Professionally, I find it questionable and unethical,’ she says. ‘The imbalance – financially, professionally, life-experience, and otherwise – between Leo and younger women creates an unhealthy and potentially abusive dynamic.’

She quotes the female comedian Ali Wong who observed that when an older man brings a younger woman to dinner ‘all the women of substance at the table are now mad at you because we have to babysit this b****!’

Leo was born to ‘hippy’ parents: German-born legal secretary Irmelin Indenbirken and comic book creator George DiCaprio.

The star’s mother revealed she chose his romantic first name when she was pregnant and he kicked her as she admired a Leonardo da Vinci painting in the Uffizi Gallery in Florence, Italy.

The pair moved to New York and then to Los Angeles where George became part of the ‘counter culture’ movement of the 1970s and was best friends with psychologist Timothy Leary, known as the ‘Godfather of LSD’.

They settled in Los Feliz, now a trendy suburb where stars such as Angelina Jolie and Brad Pitt live but, back then, was a crime-filled neighbourhood.

In an early interview, the actor recalled: ‘There used to be a major prostitution ring on my street corner, crime and violence everywhere. It’s hipster central, totally gentrified, now.’ Describing his upbringing as ‘Bohemian’, he said: ‘The earliest memory I have is me at some hippy concert with my dad and the band hadn’t come on.

‘There was an audience of hundreds of people chanting for the band and my dad scooted me on stage, I don’t know how old I was, probably three or so, and I got up there and tap-danced for hundreds of people.’ George and Irmelin split when their son was just a year old but they remained close and encouraged their only child to pursue his dreams of acting.

George remarried Peggy, a devout Sikh, who has become something of a fixture at DiCaprio’s movie premieres wearing her turban and flowing robes.

DiCaprio started his career with lucrative child modelling jobs and commercials for companies such as Matchbox toy cars. By 15, he was on the US television series Growing Pains and, at 16, was picked by Robert De Niro for coming-of-age drama This Boy’s Life, which lead to a string of critically-acclaimed independent films.

In 1996, he became a matinee idol playing the male lead in Baz Luhrmann’s Romeo + Juliet, before 1997’s Titanic – a $2.5 billion box-office triumph – made him the biggest star on the planet. He and his friends Tobey Maguire, the Spider-Man star, singer and model ‘Marky Mark’ Wahlberg, and actors Lukas Haas and Kevin Connolly, partied like rock stars while DiCaprio’s entourage – who crudely referred to themselves as ‘The P***y Posse’ – loyally defended him from the paparazzi and gold-diggers.

Wahlberg and Connolly would later write and create the HBO series Entourage based on their experiences of being around DiCaprio at that time.

Wahlberg once joked: ‘I will never admit which stories are real. They were wild times.’

Inevitably, of course, the posse grew up. Wahlberg, a devout Catholic, is now a father of four and has been married to wife Rhea Durham, a model, for 15 years.

Maguire married jewellery designer Jennifer Meyer, whose creations have been worn by Meghan Markle, in 2007 and had two children before divorcing

in 2020. A source said: ‘Tobey has always been one of Leo’s closest friends and since his divorce he’s been hanging out on yachts and partying with Leo again.’

A writer who has known DiCaprio since the Nineties says the star idolised Jack Nicholson, another notorious Hollywood womaniser who never settled down. ‘Jack became something of a mentor to Leo,’ he said. ‘People criticise Leo for being ’emotionally stunted’ but I don’t see it that way.

‘He’s living the dream. He’s worth tens of millions, has won an Oscar and dates beautiful young women. I genuinely think he’s happy.’ Another ‘mentor’ is Al Pacino who starred alongside DiCaprio in The Great Gatsby and Once Upon A Time In Hollywood.

Pacino, 84, also has a penchant for younger women, dating socialite Noor Alfallah, 30, who gave birth to his child Roman last year.

While the pair are no longer together, Pacino is said to ‘delight’ in his son.

The writer said: ‘Leo has mentors like Pacino and Nicholson who have always blazed their own trail, both professionally and personally. I don’t think Leo likes his reputation of being a womaniser.

‘I think it irritates him because he has so many other issues he’d prefer to focus people’s attention on.’ Like climate change.

DiCaprio is one of Hollywood’s most outspoken eco-warriors and heads his own charity, raising millions to fight global warming.

Yet, the writer adds: ‘It’s a sign of his immaturity that he preaches being an eco-warrior yet he takes private jets like other people take a bus.’ One dark cloud looming on DiCaprio’s horizon is his ‘association’ with rapper P Diddy who is in jail charged with heinous sexual crimes against young women and boys. Diddy vehemently denies all allegations.

When pictures emerged of DiCaprio at one of the rapper’s infamous ‘White Parties’, social media lit up. Friends of DiCaprio say it is preposterous to suggest he has ever been associated with any wrongdoing.

One source said: ‘I’ve been with Leo and I can assure you his women are always of legal age. He is swamped by girls wherever he goes. He may be nearly 50 but he’s catnip to women.

‘Of course he was photographed at Diddy’s parties. Everyone went. But Leo wasn’t friends with Diddy. That wasn’t his scene.’

To keep a low-profile, DiCaprio slips into restaurants and premieres through the back door, usually wearing a mask.

Last weekend, he went unnoticed at a Halloween party in New York until he removed his mask to sip his favourite Ciroc vodka – at which point he was ‘mobbed’ by gorgeous women.

Yet the jokes continue.

Hosting the Golden Globes award show in 2020, Ricky Gervais said DiCaprio’s movie that year was ‘so long that by the time it finished Leo’s date was too old for him’.

Director Edward Zwick, who worked with the actor on the thriller Blood Diamond revealed in his recent memoir: ‘One morning I walked into the make-up trailer and found him in the chair waiting for his turn and noticed he was paging through a Victoria’s Secret catalogue looking at the models. ‘What are you doing?’ I asked. 

‘Jenny [Jennifer Connolly, his co-star] was in the chair beside him. Without even looking over she said, ‘Shopping’.’