It's certainly no coincidence that Entourage star Kevin Connolly also happens to be a member of Leo's very own . . . you know. The two have been close since the late '90s, so much so that Leo was even a pallbearer at the funeral of Kevin's mother in March 2009.
Cutest best friends in Hollywood? Leonardo DiCaprio and Kate Winslet have come a long way since starring in 1997's Titanic. The actors forged a friendship while filming the 11-time Oscar-winning movie.
Sure, their camaraderie was noticeable during the Cannes press circuit for Once Upon a Time…in Hollywood, but their mutual respect and praise for each other's performances barely registered as anything more than normal costar behavior. Then came the news that Pitt and DiCaprio were real-life friends.
Entourage's Kevin Connolly on Leonardo DiCaprio's 'Pussy Posse' | WWHL
Who is the best friend of Brad Pitt?
Not only are George Clooney and Brad Pitt 2 of Hollywood's sexiest and most brilliant actors, but they also embody the ideal bromance. They first met on the set of Ocean's Eleven, and they've been buddies for almost 20 years.
The attention on DiCaprio's love life began in 1994, when he was linked to model Bridget Hall. He went on to date Gisele Bündchen, Blake Lively and Camila Morrone, who is 23 years his junior.
Did Leonardo DiCaprio actually draw Rose in Titanic?
No, Leonardo DiCaprio isn't actually drawing in Titanic
In this scene, which has since become a classic, where Jack (Leonardo DiCaprio) draws Rose (Kate Winslet) lying naked in front of him, the actor is unfortunately not the one who actually does the drawing.
His mother is German and his father is of Italian and German descent. His maternal grandfather, Wilhelm Indenbirken, was German, and his maternal grandmother, Helene Indenbirken, was a Russian immigrant living in Germany.
When it comes to celebrity bromances, none of them compare to Leonardo DiCaprio and Tom Hardy's friendship. The two first met on the set of their 2010 film Inception, and have been pals ever since.
The lifelong friendship of Tobey Maguire and Leonardo DiCaprio. Due to the fact that they were both child actors when they met, Leonardo DiCaprio and Tobey Maguire were destined to be best friends.
Leonardo DiCaprio and Tobey Maguire's friendship has been one of the longest to last in Hollywood. They have been best friends since they were just child actors in the 80's. And maybe this is one of the reasons that both the actors were destined to be best friends.
While filming the movie "Blood Diamond", he worked with 24 orphaned children from the SOS Children's Village in Mozambique. There was one little girl he made a close connection with and he decided to adopt her.
Jonah Hill and Leonardo DiCaprio have a fascinating friendship. The two worked together on Martin Scorsese's The Wolf of Wall Street and most recently teamed up with Adam McKay for Don't Look Up.
Neither party ever confirmed if they were dating. However, if they were indeed a thing, Rihanna would've been the second oldest woman DiCaprio has ever been in a relationship with in public, as she was 27 in 2015. It remains unclear if the pair ever did have any romantic relationship.
Promise me you'll survive. That you won't give up, no matter what happens, no matter how hopeless. Promise me now, Rose, and never let go of that promise. Rose : I promise.
The film won eleven Academy Awards—tied for most for a single film—including Best Picture and earned the 22-year-old Winslet a nomination for Best Actress. She also received Golden Globe and SAG nominations for Best Actress. Winslet did not view Titanic as a platform for bigger salaries.
Despite playing a teenager, actress Kate Winslet was 20 when filming began in 1996. With Titanic's mammoth $200 million production lasting for 160 days, Winslet actually celebrated her 21st birthday during filming, making her four years older than the character she was portraying.
“By the time girls reach 25, they're looking for more — they're looking to get married and settle down,” they said. “That is not what Leo wants. He does not want a family and does not want to be around women who may press him for that.” They continued: “The minute a girl meets him, the clock is ticking.
By August 2023, DiCaprio had moved on and began spending time with Italian model Vittoria Ceretti. Hadid followed suit in October 2023 when she was seen with actor Bradley Cooper. From their first and last outing together, here's everything to know about Leonardo DiCaprio and Gigi Hadid's relationship.
How many times has Leonardo DiCaprio been married?
Leonardo DiCaprio has never been married, but the public still seems to have a pretty good pulse on his dating life (or so we think). DiCaprio is usually linked to someone, often a much younger model. We won't insert a joke about Leo's dating life. They've all been said already.
