Leonardo DiCaprio seems to enjoy playing the real-life role of Hollywood’s ultimate bachelor. He parties on luxury yachts. He plays poker with his multimillionaire pals. He goes to the most exclusive members’ clubs, from The Bird Streets Club to The Ned. And he dates the world’s most famous models – the latest of whom happens to be fashion’s new “It” girl Vittoria Ceretti.

While his romantic relationships seem to change by the month – this summer alone there have been rumours of flings with everyone from Gigi Hadid to Neelam Gill – DiCaprio surely deserves credit for his consistency when it comes to his friend group.

These are the lucky friends who have remained a core part of Leo’s tight-knit circle:

TIGER WOODS

Who are Tiger Woods’ teen kids with ex-wife Elin Nordegren?

1. Tobey Maguire

Tobey Maguire and Leonardo DiCaprio met each other at the age of 12 and have been best buds ever since. Photo: @tobeymaguir/Instagram
One of Leo’s longest bromances is with Spider-Man actor Tobey Maguire. Their friendship dates back to the 1980s when they first got their start as child actors in the entertainment industry. Sweetly, the besties have spent the past few months living the lush life on megayachts, lounging at Club 55 Beach in France and attending Beyoncé concerts together.

2. Lukas Haas

Like Leonardo DiCaprio, Lukas Haas is an actor. Photo: @lukashaas/Instagram
Advertisement

The fellow actor, who recently starred in Babylon with Margot Robbie and Brad Pitt, also shares a tight bond with Leo. They’ve been spending more quality time together lately, as seen in recent paparazzi pics of their outings in NYC.

FAME AND CELEBRITY

What does Michael Jordan think of his son’s relationship with Larsa Pippen?

3. Vincent Laresca

Vincent Laresca is an actor who starred in Baz Luhrmann’s Romeo and Juliet alongside Leo DiCaprio. Photo: @vincentlaresca/Instagram

This actor is also one of Leo’s closest confidants and he was invited to join the Oscar-winning star to watch the elections at his Hollywood Hills compound back in 2020, according to Page Six.

Advertisement

He too has been spotted on lavish boats with Leo in recent years.

4. Richie Akiva

Richie Akiva has been dubbed the “King of New York Nightlife” and is a long term pal of DiCaprio’s. Photo: @richieakiva/Instagram

Once dubbed the “King of New York Nightlife” by Forbes, Richie Akiva is also a good pal of the Titanic actor. Per British media, he has hosted parties for celebs like Rihanna and Naomi Campbell, and was recently romantically linked to Love Island contender Arabella Chi.

His Instagram is dotted with plenty of A-listers like Justin Bieber, Jay-Z, Peggy Gou, Halsey, Alessandra Ambrosio and many more. Last week, Akiva and the Killers of the Flower Moon star reunited at Cipriani Wall Street for an event honouring Akiva, states British media.
Advertisement
CELEBRITY CHILDREN

Netflix’s Beckham: who are Posh and Becks’ 4 kids and where are they today?

5. Hillel ‘Helly’ Nahmad

Despite his reputation, the Once Upon a Time … in Hollywood actor has turned to controversial art gallery owner Hillel “Helly” Nahmad numerous times over the years. In August, he was spotted at Sardinia airport with the “disgraced” art dealer, as reported in British media.

Per The New York Times, Helly, who hails from an influential, ultra-rich family, served five months in federal prison in 2014 after pleading guilty to a charge related to a gambling ring, and was pardoned by then-president Donald Trump in 2021.

  • Leo DiCaprio loves partying, megayachts and models, but who does he hang out with these days? From Spider-Man bestie Tobey Maguire to Babylon actor Lukas Haas, both in the OG ‘Wolf Pack’
  • Many of his closest confidants are long-time friends, like Vincent Laresca and Richie Akiva, who hang out with celebs from Rihanna and Justin Bieber to Jay-Z and Alessandra Ambrosio