Stories about DiCaprio's antics have become the stuff of Hollywood legend, particularly after he joined forces with other up-and-coming actors like Tobey Maguire, Lukas Haas, and Kevin Connolly, forming a sort of band of brothers as they all tried to make it.
Other members of the so-called “Wolf Pack” besides DiCaprio, 48, and Maguire, 47, include Lukas Haas, Kevin Connolly, Vincent Lareska and Richie Akiva. Founded in the '90s, the crew was previously known as the “Pussy Posse,” as revealed in an infamous 1998 New York magazine article by Nancy Jo Sales.
Leonardo DiCaprio Gets Embarrassed When Kissed As A Teenager During His 'This Boy's Life' Interview
Did Kate Winslet and Leonardo DiCaprio get along?
Kate Winslet and Leonardo DiCaprio's chemistry in Titanic made its way offscreen as well. The Oscar-winning actors starred in the classic film early in their careers and have remained close friends since they played Jack and Rose in James Cameron's romance drama.
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.
Recently, Sydney revealed that she had a crush on her Once Upon A Time In Hollywood co-star, Leonardo DiCaprio. During an interview with IMDb, the Anyone But You star stated that Leonardo DiCaprio was her first movie star crush when she saw him for the first time in a movie.
Their romance was short-lived and by later that year, they called it quits, per E! News. In 2017, “Gossip Girl” executive producer Joshua Safran mentioned Lively and DiCaprio's former fling in an interview with Vanity Fair.
The model and actress was considered to be “the love of his life” according to The New York Daily News. DiCaprio dated Zang for fifteen months and took her as his date to the Romeo + Juliet premiere.
Sources say Paramount hoped the audience behind the series would have grown from Season 1 to Season 2, but due to the dual Hollywood strikes, the likelihood of that happening was cut short since production was stopped. Season 2 would've arrived roughly two years after Season 1 debuted.
He is the only child of Irmelin Indenbirken, a legal secretary, and George DiCaprio, an underground comix artist and distributor; they met while attending college and moved to Los Angeles after graduating. His mother is German and his father is of Italian and German descent.
Who was in the Posse? The group allegedly included stars like David Blaine, Tobey Maguire, Jay Ferguson, Josh Miller, Ethan Suplee, and Scott Bloom. But the leader was unquestionably DiCaprio. From the mid to late 1990s, DiCaprio took his squad out partying all over New York City.
Leo. Radiant and charismatic, Leo gravitates toward friends who share the spotlight. Aries and Sagittarius, Fire signs, match Leo's enthusiasm and zest for life. Gemini and Libra, Air signs, add a touch of intellectual flair and engaging conversations.
The primary sign Leos find it difficult in getting along with is Taurus. Taurus moves at a steadier speed than Leo making it difficult for the Bull to pause and rest, which causes disappointments between the two. The second sign Leos might battle with is Scorpio.
Is named after Leonardo Da Vinci because he first kicked in his mother's womb when she saw Leonardo Da Vinci's artwork at the Uffizi Gallery, his artist father felt it was apt. His paternal grandfather's middle name happens to be Leon. Robert De Niro and Jack Nicholson are his favorite actors.
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.
The couple first crossed paths in 2010 while filming “Green Lantern.” Lively and Reynolds were love interests in the movie, but were romantically linked to others in real life at the time: Lively was dating her “Gossip Girl” co-star Penn Badgley and Reynolds was married to Scarlett Johansson.
Sophie Dodd is a freelance writer for PEOPLE. She previously worked as an editorial assistant at PEOPLE from 2018 to 2022. Leonardo DiCaprio and Gigi Hadid had a brief romance. The Revenant actor and the model first made headlines when they were spotted together at a New York Fashion Week afterparty in September 2022.
Did Kate Winslet have a crush on Leonardo DiCaprio?
"It's so disappointing for people to hear that, because in the soap opera of the Kate and Leo story we fell in love at first sight and had a million snogs, but actually we never did.
Has Leonardo DiCaprio ever dated someone older than him?
Documented most succinctly in this now infamous chart, all of his high-profile relationships have been with women under the age of 25. His last relationship, with actor and model Camila Morrone, ended this past August, shortly after she turned 25.
Are Kate Winslet and Leonardo DiCaprio good friends?
In 1997 a decades-long friendship between Kate Winslet and Leonardo DiCaprio was born when they starred together in Titanic. Their close bond has become internet lore, and now British actress Kate has given a rare glimpse into what their friendship looks like after 26 years.
Leonardo DiCaprio spent some quality time with his friends this weekend! The 48-year-old Oscar-winning actor was seen hanging out with longtime BFF Lukas Haas and other pals on Saturday night (March 25) in downtown Manhattan in New York City.
The longtime friends were photographed going to Hotel Plaza Athénée in Paris on Wednesday, where they were attending an event with LeBron James. DiCaprio, 48, was photographed talking on his phone while entering, and Maguire, 47, followed behind, also wearing a Los Angeles Dodgers baseball cap and mask.
