Next Sunday evening, Leonardo DiCaprio will find himself in a theater a short distance from his childhood home, eagerly anticipating whether he will be awarded the Best Actor Oscar for his role in One Battle After Another.

This marks his sixth nomination for the prestigious award, equalling the record held by acting legends like Daniel Day-Lewis and Richard Burton. Interestingly, DiCaprio is still relatively young at 51.

Regardless of the outcome, DiCaprio is likely to skip the celebratory after-parties. Over the years, he has maintained a low profile, earning comparisons to Hollywood icon Howard Hughes. Having portrayed Hughes in Martin Scorsese’s 2004 film The Aviator, DiCaprio has expressed that it’s a film he revisits often. Much like Hughes, he now tends to avoid places where the media might be lurking.

And honestly, I can’t fault him for that. If anyone deserves blame, it might just be me.

DiCaprio occupies a unique and intricate role in our cultural landscape. Renowned for his acting prowess, he is a favorite among directors. Paul Thomas Anderson, upon winning the Bafta for Best Director for One Battle After Another last month, offered a heartfelt thanks to DiCaprio. Beyond acting, he is a fervent environmental advocate, a socialite known for extravagant yacht parties, and a private island owner. He even attended Jeff Bezos’ wedding. While many see him as the ultimate dream partner, others criticize his preference for dating significantly younger women.

At the Golden Globes in January, host Nikki Glaser humorously remarked on DiCaprio’s impressive career, noting his countless iconic roles, collaborations with top directors, three Golden Globes, an Oscar, and jested about his relationship history, saying, “And the most impressive thing is you were able to accomplish all that before your girlfriend turned 30.”

You could see why he might not want to be in the public eye that much.

I do not like to think that I contributed to the fact that he has increasingly retreated and done very few lengthy interviews in the last quarter of a century. But I imagine I did.

Because I spent a night with DiCaprio in Los Angeles for a Time magazine cover story in 2000 about his upcoming movie The Beach, which was really about what it was like to be the biggest celebrity in the world. It had been two years since his last film, Titanic, had come out.

I was 28. He was 25. To my surprise, we were both nervous. Me because he was Leonardo DiCaprio. He because he was Leonardo DiCaprio. The more he exposed parts of his personality in the press, he explained, the less effective they’d be when he used them in a character.

‘I want to be as dry and drab and as boring as possible,’ he told me.

We met at 6.30pm on a Sunday at the Chateau Marmont, West Hollywood, in a room that the film studio booked just so we could sit there. And that’s all we did. Because DiCaprio was too worried about revealing anything. 

Eventually, it got so bad that we watched TV. This was back in the days of channel flipping, and he landed on What’s Eating Gilbert Grape?, the 1993 film that earned him his first Oscar nomination at 19. He perfectly recreated the character, who had an intellectual disability, for me. We also drank a pot of oolong tea from room service. And then milkshakes. He dismissed any reason to leave the room. We sat quietly. It was not going great.

Eventually, I expressed my nervousness about not having anything to write about. Which surprised him. He figured I’d come in with an angle. I told him that I didn’t. And I was worried I wouldn’t be able to come up with one.

For the first time, he said, he felt included in the process of being written about. He suggested I write about how environmental concerns motivated his upcoming film, The Beach, which centred on the search for a Thai island unspoiled by humans.

He got excited and told me he’d show me the journal entries he wrote while shooting the movie in Thailand. Two days later, he faxed me two pages of it, which included sentences such as, ‘The carbon dioxide in the Earth’s atmosphere is having disastrous and irreparable effects on our climate.’

When he went to the bathroom, I looked down at his open wallet – which I truly did not touch – and saw a membership card to a mid-range supermarket chain called Ralphs. 

I did not believe a man getting paid $20million (£15million) a film was bargain-shopping for groceries. He insisted he was. I suggested we finally leave the hotel room and do some shopping. He refused. Then I offered to pay for all the groceries he could buy. He found this impossible to refuse.

He called his friend, the actor Ethan Suplee, who met us at the hotel. Then DiCaprio got his car from the hotel garage and drove us all to the Rock & Roll Ralphs, just a mile down Sunset Boulevard from the Chateau Marmont.

He put on a Puma baseball cap and some glasses to go with his baggy drawstring pants, T-shirt with a devil on it, and a chain holding a cross his grandmother used to wear. We went inside and… no one noticed. The two actors ran around the supermarket, DiCaprio riding inside the cart, later lifting it over a cereal display, and not once being spotted by fans.

I paid for his $155.36 groceries (using his membership card for savings), which included two packs of waffle mix ($4.07 each), four Canada Dry ginger ales ($1.19 each), a sweet ginger teriyaki glaze ($4.57) and two beef tenderloin cuts ($7 each). I helped load the bags into his trunk in the parking lot, said goodbye, and headed to my hotel.

Back in New York, I wrote a profile about DiCaprio’s commitment to the environment, quoting liberally from his earnest journal entries. The editor of the magazine read it and told me: ‘I didn’t send our youngest entertainment writer to Los Angeles to hang out with a Hollywood heart-throb for an article about global warming.’ My piece, he explained, was supposed to be fun.

In a panic, I wrote a parody of the tabloid magazines of the time, annotating the Ralphs receipt with ridiculous personality analysis based on each purchase. I circled the yogurt on the receipt and wrote, ‘At first, he mocked yogurt as “wussy” but then he noticed the high-protein content and the manufacturer’s environmental content.

“I commend this Stonyfield Farm stuff,” he said.’ When the issue came out, with the headline What’s Eating Leonardo DiCaprio?, his publicist called to say how great the article was.

Then he called back.

DiCaprio was furious. I had bamboozled him. I had tricked him into trusting me by pretending I was going to write about the environment, and instead shallowly analysed his personality based on his soda purchases. I was another member of the deceitful press.

He complained about this for years, telling Vanity Fair in 2004, ‘He prints my grocery list… I seemed like the most immature, juvenile punk in all of these articles that were written about me.’ He’d run into people who worked at Time and asked if they knew me. One of my best friends went with, ‘Vaguely. He works in the office’. And then agreed about what a b*****d I am.

So, for years, I’ve avoided him. Which you wouldn’t think would be hard. But I somehow moved from New York to Los Feliz, the tiny part of LA where he grew up.

When my wife took me to look at an open house on our block in 2021, DiCaprio was checking it out too (possibly for his mother, for whom he wound up buying a different Los Feliz home). Luckily I – like those Ralphs shoppers – didn’t notice him because he had his baseball cap pulled low, but I was eager to leave as soon as my wife told me.

 And I get nervous whenever I go to my local Los Feliz Branch Library, which has a ‘Leonardo DiCaprio Computer Center’ funded by the star and decorated with signed posters of him from 1998. Though he has an apartment in New York and an island off Belize, he lives in the same Hollywood Hills area as I do. He bought his dad a house there, too.

What I should have done back in 2000, which now seems obvious to me, was to call his agent and explain that my editor didn’t like the stuff we had agreed on about the environment.

But he was Leonardo DiCaprio, and my carefully negotiated night with him was long over. Contacting him seemed as impossible as… contacting Leonardo DiCaprio. Plus, engaging a subject about what was going to be written about him seemed like the kind of thing that real journalists at Time would disapprove of. And the rewrite happened so fast. And… I should have told him.

He, as you might have heard, has nevertheless recovered nicely from my betrayal. And he has become one of my favourite actors.

In the Time article I wrote, ‘Nothing happens besides deliberation in the brownie-mix aisle… and a good deal of time spent choosing steaks. And quite a few minutes debating the merits of ginger-ale brands. And waffle mixes. And protein bars. DiCaprio is the Hamlet of Ralphs.’ And I wasn’t totally wrong in analysing him as Hamlet-like. ‘The thing he hates most in life is making a decision,’ Baz Luhrmann, who had directed him in 1996’s Romeo + Juliet, told me for the article. ‘It’s a pain to get Leo to commit to anything in life, particularly a role.’

But those decisions have been great, including One Battle After Another, in which his performance as a former radical is packed with sadness, hope, frustration, humour and the redemption of parental love. As always, his presence is intense, his brow prepared to furrow, his finger ready to poke defiantly in the air.

It’s what Spielberg once told The New York Times after shooting Catch Me If You Can: ‘The thing I often say to Leo is, “Don’t ever lose that little boy in you who can get his feelings hurt so effortlessly. That’s going to serve you well as an actor.”’ If I’d known that about him, maybe I’d have been more careful. Instead, he has figured out how to protect himself and his work by not letting the press hurt his feelings.

And next week, win or lose, we’ll be reminded how well that has served him as an actor, just as he said it would 26 years ago.

Here’s what we DO know about Leonardo DiCaprio 

He only dates models in their 20s

In Variety’s ‘Actors on Actors’ interview late last year, Jennifer Lawrence made a jab about DiCaprio’s history of dating very young women. ‘I’d really love seeing you be a dad,’ she joked about his role in One Battle After Another. ‘I’m so sad that you don’t have a teenage daughter. You’d look great with one.’ He grimaced and shifted in his seat. Sources had previously told Us Weekly that ‘he doesn’t see himself ever getting married’ and is ‘indifferent’ about having children.

His current girlfriend, Italian model Vittoria Ceretti, 27, is one of his oldest yet. The two met in 2023 at the Cannes premiere of his film Killers Of The Flower Moon when DiCaprio was 48, Ceretti 24. His previous girlfriends include model (and The Night Manager star) Camila Morrone, who was 20 when they met in 2017; model Nina Agdal, who was 24 when they dated in 2016; and, model Toni Garrn, aged 20 when they dated in 2014. To date, Hollywood’s most famous commitment-phobe has never been linked to a woman older than 30.

Romance doesn’t seem to be DiCaprio’s strong point, anyway. According to a previous conquest, his bedroom antics are, to put it mildly, peculiar: when he spots someone he likes in a bar, his bodyguard taps the girl on the shoulder and invites her to his hotel room. There, he reportedly strips alone in the bathroom, switches off the lights and puts headphones on during the act, then gets an assistant to send the girl home in a taxi.

He’s an eco warrior… well, mostly

To give DiCaprio credit, he was talking about the environment long before much of Hollywood. In 1998 he set up the Leonardo DiCaprio Foundation (now Re:Wild), a non-profit focused on protecting conservation zones, which has since donated more than £80 million to over 200 projects.

In 2007, he released the documentary The 11th Hour, speaking to 50 world-leading experts about ways to save the planet; and in 2014 he called the UN to action, saying, ‘The time to answer the greatest challenge of our existence on this planet is now.’ In 2016 he met Pope Francis at the Vatican to discuss their shared commitment to environmental protection. He also bought Blackadore Caye, a private island off Belize, for around £1.25 million in 2005, where he’s apparently planning to open a luxury eco-resort highlighting the island’s nature reserves. It was meant to open in 2018, then 2020, then 2021. As of 2026 it is still unopened (and largely unbuilt).

His one Oscar win, so far, came in 2016 for the Western thriller The Revenant. In his acceptance speech, he called climate change the ‘most urgent threat facing our entire species’ and raged against the ‘politics of greed’.

A couple of months later, he travelled 8,000 miles to pick up an environmental award via private jet. Last summer he was snapped aboard Jeff Bezos’ £370 million superyacht – which generates 7,000 tons of carbon emissions per year, roughly 447 times the entire annual carbon footprint produced by your average person.

He still has his teen friends

When asked about DiCaprio’s friends in 2013, a Hollywood producer told Esquire, ‘How normal is it for anyone to have the same friends he had when he was 13 years old? Things change. But for Leo, nothing ever really changes.’

His closest friend, Tobey Maguire (aka the 2000s Spiderman), has been around even longer. According to DiCaprio, when the two were about 11, he spotted Maguire out the car window, making a TV show on a street in LA.

He told his mum to stop the car, and ‘literally jumped out. I was like, “Tobey! Tobey! Hey! Hey!” And he was like, “Oh, yeah – I know you. You’re… that guy.” But I just made him my pal. When I want someone to be my friend, I just make them my friend.’

The pair met fellow actors Kevin Connolly and Lukas Haas as teenagers and became the ‘Pussy Posse’, notorious for their rowdy, girl-crazed lifestyle (the group regularly attended Sean Combs’ ‘white’ parties). 

They’re still DiCaprio’s closest friends: he was spotted dancing with Maguire at a Super Bowl after-party last month and is ‘Uncle Leo’ to the actor’s kids. He’s so close to Connolly that he was a pallbearer at his mother’s funeral in 2009. Apparently, they have rebranded themselves as ‘The Wolf Pack’, with one 2016 Oscars-goer saying they were ‘howling like wolves all night. They kept chanting, “Wolf Pack, Wolf Pack, Wolf Pack!”’

DiCaprio has had the same manager, Rick Yorn, since he was signed at 19 in 1993; and he has stayed close with Titanic co-star Kate Winslet, who he gave away at her 2012 wedding. And there are other special ‘colleagues’: Teyana Taylor, his One Battle After Another co-star; and Brad Pitt from Once Upon A Time In Hollywood.

But close friends? Like that producer told Esquire, it’s the same handful of boys he met as a teenager.

He loves his mum

DiCaprio is – unsurprisingly, given his dad moved out when he was a year old – a mummy’s boy. It was Irmelin Indenbirken who raised him, working as a legal secretary to support the family. When he turned ten, she would drive him three hours a day from their rough East LA neighbourhood, so DiCaprio could attend a fancy school rather than the local one. Most evenings, she’d take him to auditions. Thirty years on, while picking up a gong at the 2014 Golden Globes, he called his mum (and date for the evening) a ‘walking miracle’.

She has been his date to numerous other awards ceremonies, including the Oscars when he won in 2016 and this year’s Baftas, where he joined his One Battle After Another castmates on stage to collect the Best Film trophy. His gifts to her include a £5million LA home and a VRAI lab-grown diamond necklace, worth tens of thousands.

He’s now reclusive

For all the superyachts and supermodels, a source says: ‘Leo has realised he functions best when he steps away completely. He wants quiet, he wants stillness – and he’s not pretending otherwise.’ Another insider put it more bluntly: ‘He’s not out there courting fame any more – he’s out there avoiding it.’ He’s rarely photographed without a cap, face mask and sunglasses, refuses all event appearances unless he’s campaigning for awards season, and lives like a ‘hermit’ between jobs, rarely leaving the house.

It’s not just personal preference, but a considered career move. He has said that, after Titanic, ‘I was like, OK, how do I have a long career? I feel like the best way is to get out of people’s faces.’

He takes acting seriously

While many of his peers signed up for lucrative franchises like Marvel, DiCaprio’s priority has always been fewer films, bigger directors and heavyweight roles. He has spoken often about wanting to work with ‘the best of the best’, teaming up repeatedly with Martin Scorsese, Quentin Tarantino and Baz Luhrmann, and waiting years between projects until the right script comes along.

When he commits, he commits completely. For The Revenant, he ate raw bison liver, slept inside animal carcasses and endured sub-zero temperatures when filming. For The Wolf Of Wall Street, he spent months studying real-life traders to perfect the film’s manic, hedonistic energy. Co-stars and crew routinely describe him as intense, focused and relentlessly prepared – the first to arrive on set and the last to leave. In his Baftas speech last month, One Battle After Another director Paul Thomas Anderson said, ‘Leo asks you all the right questions and, as any director knows, that makes you find the right answers.’

It seems to have paid off. Six Best Actor Oscar nominations, one win (so far), and a reputation as one of the greatest actors of a generation. Just don’t expect him to be showboating like Chalamet on the red carpet. As he told Deadline last year: ‘It is about saying, “I want to be here for a long time. I don’t want to be overexposed.”’

Words: Scarlett Dargan