Leonardo DiCaprio kicked off his diverse career when he was a kid, first appearing in a couple of TV series and features before What’s Eating Gilbert Grape, The Basketball Diaries, Romeo + Juliet, and, of course, Titanic, catapulted him onto the A-list, making the young actor one of the biggest movie stars in the world. Since then, DiCaprio has been a household name, stacking up his cinematic roles, nominations, and awards, even finally winning his first Oscar for Best Actor in 2015’s The Revenant.
Tobey Maguire’s career began in a similar fashion, starting young in the child acting scene, though his professional life didn’t quite take off the way DiCaprio’s did after they both appeared in 1993’s This Boy’s Life when they were teenagers. Maguire, best known for playing Peter Parker in Sam Raimi’s Spider-Man trilogy that kicked off in 2002, has a handful of acclaimed movies under his belt. In 2010, Maguire earned a Golden Globe nomination as Best Actor for his performance in the drama Brothers and only did a few more projects after that before seemingly stepping away from the acting world to focus on producing.
DiCaprio and Maguire could have easily ended up as Hollywood rivals, as they were constantly going after the same roles ever since they were kids. Instead, the two formed a quick bond nearly 30 years ago and never looked back, even during times of controversy. This is the truth about Leonardo DiCaprio and Tobey Maguire’s relationship.
Leonardo DiCaprio and Tobey Maguire's friendship is a tale as old as time
The actors have been friends for over three decades, dating back to when the up-and-coming stars were not even teenagers yet. According to a profile DiCaprio did with Esquire in their May 2013 issue, the ease of the two becoming best friends had a lot to do with the fact that they had so much in common. DiCaprio and Maguire were both raised in Los Angeles by single mothers, for example, and were both navigating the LA world of child acting in a competitive Hollywood environment.
According to Esquire, DiCaprio sought out a friendship with Maguire when the two stars were only 12 years old. The actor was apparently heading home from school when he spotted Maguire filming a TV show in Los Angeles, recognizing the other boy from auditions for other projects. DiCaprio told Esquire that he “literally jumped out of the car” after telling his mother to stop, and excitedly began yelling “Tobey! Tobey!” to grab Maguire’s attention, sparking the beginning of a real friendship.
Maguire told Esquire that DiCaprio’s sense of purpose is what makes him successful personally and professionally, saying, “You don’t become as successful as Leo if you don’t know how to get what you want,” even friends. DiCaprio shared that when he wants someone to be his friend, “I just make them my friend,” and the rest is history.
Leonardo DiCaprio and Tobey Maguire are founding members of the infamous P***y Posse
According to Complex, DiCaprio’s infamous group began with Leonardo DiCaprio, Tobey Maguire, Kevin Connolly, and Lukas Haas. They were known to chase girls, set off stink bombs at Sky Bar, sneak into Victoria’s Secret events, and make last-minute trips to Vegas if they weren’t working or partying in Hollywood. It didn’t take long for people in the industry to give the group a nickname, referring to the guys as the P***y Posse.
The group was apparently formed by DiCaprio as a way to protect himself from certain people, though, according to Complex. In 1996, DiCaprio told Detour that he “can’t stand bad***es” and prefers having “sweet people around.” The group, which, according to PopSugar, has included other celebrities such as Jay R. Ferguson, David Blaine, Jonah Hill, and Orlando Bloom, and, over the years, has also served as a crew of young actors building friendships and a solid support system. An anonymous source told New York Magazine that some of the actors in the group “have completely lost their careers,” so “all they do now is hang out with Leo.” Between the VIP treatment and lifelong friendships, that doesn’t sound like a bad gig.
The Posse has also been known to get into trouble over the years. According to NY Mag, DiCaprio and Ferguson allegedly assaulted actor Roger Wilson on one occasion, for example, and a young DiCaprio was reportedly spotted once throwing litter onto cars off of the Brooklyn Promenade.
The '90s indie film Leonardo DiCaprio and Tobey Maguire never want you to see
Controversy only makes the heart grow fonder, right? Over 20 years ago, DiCaprio and Maguire collaborated with a handful of friends to make a black-and-white movie titled Don’s Plum. According to Vanity Fair, it’s the one movie both actors never want their American fans to see. Don’s Plum was filmed in the summer of 1995 and part of 1996, over six total days, featuring Kevin Connolly and Scott Bloom alongside the best friends, as well as Amber Benson, Heather McComb, Meadow Sisto, and Jenny Lewis. One of the movie’s producers, Dale Wheatley, told the New York Post that DiCaprio became “immediately apprehensive” when they found out the ad-libbed short was being turned into an indie feature. According to the NYP, the movie was ultimately banned from the U.S. after the duo counter-sued the creators in 1998.
Wheatley violated the 1999 settlement after posting the movie on the internet in 2014 where it stayed for 16 months. According to the NYP, Wheatley accused DiCaprio and Maguire of being the “bully posse,” calling them “terribly intimidating with their power and their influence.” Wheatley also alleged that the lawsuit had less to do with the movie’s subject matter or the film’s length, and more to do with Maguire “feeling that Leo had outshined him.” A spokesperson for DiCaprio reached out to the New York Post stating that Wheatley’s comments are “decades-old lies” fabricated “in an effort to gain publicity and unlawful financial gain.”
Leonardo DiCaprio and Tobey Maguire love starring in movies together
Being best friends for 30 years comes with its perks, and when you’re both movie stars, this includes getting to collaborate on cinematic projects. Setting aside the controversial indie film that the duo treats like Voldemort’s name, the first big movie the actors starred in together was 2013’s The Great Gatsby adaptation.
According to an interview with The Associated Press (via The Oklahoman), the stars had wanted to work together for a long time, but it didn’t feel right until The Great Gatsby came along. Writer and director Baz Luhrmann remarked that DiCaprio and Maguire have “a true partnership,” which meant the duo was determined to be “brutally honest with one another” as they collaborated on the movie together. DiCaprio told the outlet that he and Maguire would constantly ask each other how they felt about a scene, carrying out their “very own distinct private conversations about everything.”
According to that same interview with The Associated Press, Maguire said he and DiCaprio have maintained a healthy balance between the movie industry and their friendship, including seemingly endless support for each other’s work. For example, DiCaprio apparently had a party to celebrate Maguire’s stellar performance in the 2009 drama Brothers, which also starred Jake Gyllenhaal. DiCaprio told the outlet that having “similar upbringings” and “humble beginnings” while being so enthusiastic and ambitious drew them closer together and only made their work life stronger.
Leonardo DiCaprio and Tobey Maguire are… neighbors?
You know you’re tight with your best friend when you end up as neighbors. According to an interview with The Associated Press (via The Oklahoman), Maguire and DiCaprio used to live next door to each other. The fun fact was revealed when Maguire was discussing how his pal contacted him in order to discuss The Great Gatsby, and Maguire said thanks to their respective homes’ close proximity, “it wasn’t a far journey,” telling DiCaprio he could “be over in 30 seconds.” According to Sheltr Group, DiCaprio and Maguire used to live in The Bird Streets in Los Angeles, described as “luxury living for the young and wealthy.”
Living in close proximity seems to have strengthened an already solid bond as the duo not only worked closely together to make The Great Gatsby the project they had envisioned, but in having each other’s backs in all walks of Hollywood life. According to that same interview with The Associated Press, the duo knows they can rely on each other when they need advice, including chats about every movie they do. “Every single choice I’ve made, I’ve talked to Tobey about and vice versa,” shared DiCaprio. “We’ve had endless conversations about certain projects and argued with one another and supported one another along the way.”
Leonardo DiCaprio and Tobey Maguire's wild yacht parties
According to Vanity Fair, the two friends love partying it up on expensive yachts. For instance, the publication reported in 2016 that the duo traveled to Ibiza, Spain along with a few other friends after attending a fundraising event for the Leonardo DiCaprio Foundation. Vanity Fair also claimed that, at the time, a grainy photo from a long-lens camera had been shared online, capturing the friends enjoying the view of the vista. The media outlet noted that DiCaprio and Maguire are known to travel together, and as history repeats, their yacht parties seem to be a tradition following DiCaprio’s fundraising events for his environmental foundation.
The following year, People reported that DiCaprio and Maguire, again with a group of friends, had been spotted partying on a luxury yacht called the Impromptu in the south of France off the coast of St. Tropez. The trip was apparently a celebration after another successful night for the Leonardo DiCaprio Foundation’s fundraising charity event in the area. according to Vanity Fair, swimsuit model Nina Agdal had been among the group of friends during the previous yacht trip and had been rumored to be dating DiCaprio. According to People, the 2017 yacht party was sans Agdal after the two apparently split up after dating for a year, reportedly resulting in DiCaprio spending more time with friends like Maguire following the breakup.
Leonardo DiCaprio and Tobey Maguire are not competitive with each other
DiCaprio and Maguire have seemingly never allowed the pressure of Hollywood to affect their friendship. People reported that when the two first met during the arduous auditioning process, it was for the TV series Parenthood, in which DiCaprio landed the lead role and Maguire had a couple of lines on the one-season series. According to PopSugar, Maguire lost out on two other roles to DiCaprio, one in Critters 3 and the other in This Boy’s Life. Going after the same roles and often being bested by DiCaprio has apparently never damaged their friendship, nor did it prevent them from becoming as close as they are. Maguire told People: “Leo and I have a lot of trust and respect for each other. We have a close friendship and I definitely have an affection for Leo.”
According to an interview with The Associated Press (via The Oklahoman), a key aspect of DiCaprio and Maguire maintaining a strong relationship in the world of Hollywood is a pact the two made long ago that if one of them got a lead part in a project they were both interested in, the other would help their friend get a supporting role. After DiCaprio got the lead part opposite Robert De Niro in This Boy’s Life, for example, Maguire appeared in the feature, playing a friend of DiCaprio’s character.
Uncle Leo to Tobey's kids
DiCaprio might not be a father himself, but apparently his softer dad side comes out as he plays Uncle Leo to Maguire’s kids. According to People, DiCaprio has taken on an uncle role with Maguire’s young children, Ruby and Otis, flexing his father figure muscles. Even though the ladies man doesn’t have any kids of his own, a source told the media outlet in 2016 that DiCaprio is “a natural” with the kids, including paying them lots of attention, “cutting up their food,” and tagging along for “family friendly activities” with Maguire and his wife at the time, Jennifer Meyer.
According to People’s source, the love affair is two-sided as Maguire’s kids apparently adore Uncle Leo. “They will visit the beach, or grab Sunday brunch. Leo is great with Ruby and Otis,” the anonymous source shared, including that DiCaprio is very hands-on and would make a great dad himself.
Leonardo DiCaprio and Tobey Maguire are saving the environment, one gala at a time
According to the Leonardo DiCaprio Foundation website, the organization supports projects worldwide that “build climate resiliency, protect vulnerable wildlife, and restore balance to threatened ecosystems and communities.” The foundation holds an annual gala in St. Tropez, France, featuring auction items that include art, celebrity memorabilia, and travel adventures.
Maguire is a regular attendee at the event, such as when he came out to support his friend at the fourth annual gala in 2017, where Kate Winslet also appeared for a Titanic reunion, as reported by People. During the third annual gala in the previous year, Maguire also attended as one of the event chairs alongside other stars such as Cate Blanchett, Robert De Niro, Penelope Cruz, Jonah Hill, Edward Norton, and Charlize Theron, as reported by Forbes.
DiCaprio’s foundation and annual gala is not the only charity the duo have supported together. In 2017, DiCaprio and Maguire were spotted by the Storm Shadow Crew at the Fashion For Relief Fashion Show charity event in support of Save the Children in Cannes, France. In 2018, DiCaprio held another charity auction, this time at Jackson Park Ranch in Santa Rosa, California, raising millions more for the environment with, you guessed it, Maguire among more than 300 guests, as reported by Sonoma Magazine.
Leonardo DiCaprio and Tobey Maguire are average pals who live glamorous life-styles
Despite the Hollywood lifestyle full of yacht parties and lucrative charity events, the old friends say they have an average friendship. Maguire told People that he and DiCaprio “have a lot of trust and respect for each other,” and that they are “like any other buddies.” The two share plenty of laughter, talks, and have a lot in common, especially their passion for basketball.
The two are known to frequent basketball events, and according to PopSugar, the duo has attended Lakers games together for years. They also enjoy the occasional dinner date night, such as when they went out to grab a bite to eat in West Hollywood with each other’s families including Maguire, his children, his estranged wife Meyer, and DiCaprio’s parents, as reported by Daily Mail. Of course, the buddies also enjoy hanging out with their mutual famous friends, such as Orlando Bloom, who was spotted grabbing a bite to eat, snacking on some ice cream, and going on a stroll with DiCaprio and Maguire in New York City, as reported by People. Who wouldn’t want to spend time around the close-knit friends?
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