Brad Pitt and Leonardo DiCaprio are two of the biggest movie stars of their generation. But they only shared the screen for the first time in 2019 on Quentin Tarantino’s Once Upon a Time… in Hollywood. However, while promoting the film they suggested that they might not get such an opportunity again.
Quentin Tarantino’s love letter to 1960s Los Angeles stars DiCaprio as a fading star struggling to stay relevant. Pitt plays his stunt double and best friend whose own career suffers as a result. And although the box office receipts and awards glory would suggest otherwise, the pair believe that this, in part, is a case of art imitating life.
Pitt and DiCaprio gave a series of interviews ahead of the release of Once Upon a Time… in Hollywood. And in several they mentioned the changes they’ve witnessed as they settle into middle age. Here’s a look at their budding bromance and how they no longer feel assured of their status in Tinseltown.
Although Pitt and DiCaprio hadn’t previously appeared on the big screen together, they have travelled in similar circles since the early 1990s. Before they shot to worldwide fame, they both appeared in ABC’s prime-time sitcom Growing Pains. And DiCaprio reportedly inspired Gwyneth Paltrow to become a vegan during her three-year relationship with Pitt.
In 2015, both actors appeared in The Audition, a short directed by Martin Scorsese. Doubling up as a commercial for the Studio City Macau resort, the film saw DiCaprio and Pitt appear as themselves alongside another Hollywood icon, Robert De Niro. However, they never actually spoke to each other on camera.
The two A-listers only exchanged dialogue for the first time when Quentin Tarantino cast them in 2019’s Once Upon a Time… in Hollywood. And Pitt told The New York Times that they instantly bonded over their shared experiences. He said, “It was pretty automatic. We both came on the scene around the same time, we have crossed paths many times, we have the same reference points.”
“I’ve always felt that you don’t understand the deal you’re making when suddenly you’re that lone gazelle on the plain and the herd’s gone, so to speak,” Pitt continued. “So there’s automatic comfort in having experienced the same thing in that way. That’s not a complaint in any way, I say that merely as fact. We have mutual respect and I know when an actor elevates a scene, so we carry that respect.”
Pitt continued to be effusive about DiCaprio at the Cannes Film Festival. He told reporters, “It was really great ease and really great fun. It’s that thing of knowing you’ve got the best of the best on the opposite side of the table holding up the scene with you and there’s great relief in that.”
And DiCaprio has been just as keen to sing the praises of his co-star. “Brad is not only a terrific actor, but he’s a professional,” he said at a Cannes press conference. “So when Quentin puts you in these improvised scenarios, we both have a foothold on our history and our character. I have to say it was incredibly easy – incredibly easy working with Brad.”
DiCaprio also enthused about Pitt while speaking to E! News ahead of the movie’s premiere. He said, “[Pitt’s] not only made great choices as an actor, not only is he extremely talented, but he’s incredibly easy to work with. And that’s the dynamic that I think both of us needed in this film.”
And the compliments continued when DiCaprio spoke to Deadline. He said, “What was very interesting about working with Brad was this strange inherent comfort and ease that we really both clicked into day one. It didn’t need a lot of prep work. We talked about the script, and we instinctively knew that dynamic and relationship, and who these guys were to one another.”
The pair also raved about each other when they both appeared on NBC’s Today. When asked whether he felt any pressure about appearing on screen with DiCaprio, Pitt replied, “Hell no, man. You don’t have to carry the whole thing. You’ve got these other great people who are the best of the best and are going to help carry that load. It’s actually a relief.”
Unsurprisingly, DiCaprio also agreed with his new best bud. He said, “I don’t think either of us thought about it in that context. It’s what’s best for the film.” He was also keen to praise Pitt, “I’ve admired the choices that he’s taken through his career. You’re trying to create a piece of art here.”
So why did it take so long for Pitt and DiCaprio to work together? Well, Pitt wasn’t in the mood to give a serious answer when asked by Extra. He quipped, “Yeah, I had a restraining order against him for a while… incident in ’94 we don’t like to talk about.”
Thankfully, Tarantino was a little more serious when he was asked by GQ Australia why he decided to bring the two actors together for the first time. Referring to Pitt, the director said, “I thought he would be terrific in this character because it needs a terrific actor. But it also needs a movie star, and particularly a movie star like Mr Pitt, a movie star that I think audiences like watching.
On the subject of DiCaprio, Tarantino said, “I absolutely had him in mind, but I didn’t know if I was going to get him. I’m not presumptuous. I mean, everyone in the world wants him.” Tarantino had previously worked with DiCaprio on Django Unchained and Pitt on another revisionist history tale, Inglourious Basterds.
The co-stars are said to have developed such a strong friendship that they have also started hanging out in their spare time, too. British newspaper The Sun claims that DiCaprio is a regular visitor to Pitt’s house where the pair indulge in their love of sculpting. An insider said, “Leo brings sandwiches over from their favorite place, Fat Sal’s and they spend their boys’ nights creating art until the early hours.”
Pitt and DiCaprio continued their very public love-in when awards season came around. At the Golden Globes, the former picked up Best Performance by an Actor in a Supporting Role for his turn as Cliff Booth. And in his acceptance speech he thanked his “partner-in-crime,” claiming that he would have “shared the raft” in a reference to that famous scene from Titanic.
An in-form Pitt then told the star-studded audience, “You know, before The Revenant, I used to watch, year after year, his co-stars accept awards and get up and thank him profusely. I know why. He’s an all-star, he’s a gent, and I wouldn’t be here without you, man. I thank you.”
Pitt continued to happily discuss his A-list bromance while on the red carpet of the Screen Actors Guild Awards later that same month. He even told PeopleTV that DiCaprio had given him a rather intimate nickname. “He calls me ‘Lover,’” Pitt revealed. “It’s a bit confusing, but I roll with it.”
And Pitt also spoke of his admiration for DiCaprio after the ceremony, describing him as “so committed.” The actor continued, “Like within a scene. You can play a scene at level one or 11, and he’s always pushing for the edge. He’s not protecting himself in any way. Sometimes, you will kind of put the reins on, but he’s literally throwing himself out there. He goes all the way and it’s really impressive.”
As you’d expect, the pair appear very keen on the possibility of working together again. “Of course,” was DiCaprio’s response when he was asked about the matter on NBC’s Today. Pitt even expressed his ideas of forging a Dean Martin and Jerry Lewis-style partnership to make several movies and a Christmas album. Although he said this with his tongue firmly in his cheek.
Of course, both parties will first work on various other projects separately first. DiCaprio has reportedly signed up to play cop Joe Petrosino in an adaptation of Stephan Talty’s true-crime book The Black Hand. He will also portray Leonardo da Vinci in a biopic of the artist produced by his own Appian Way company.
But da Vinci isn’t the only real life figure DiCaprio is due to take on. He will also bring Theodore Roosevelt back to life in a biopic of the United States President helmed by regular collaborator Martin Scorsese. DiCaprio will also team up with Scorsese on an adaptation of David Grann’s non-fiction book about the birth of the FBI, Killers of the Flower Moon.
And Pitt is arguably even busier than DiCaprio. He will serve as producer on no fewer than four films in 2020 alone. These include crime drama Kajillionaire, Sundance hit Minari, political comedy Irresistible and the adaptation of Joyce Carol Oates’ Blonde. And they aren’t the only Pitt projects in the pipeline, either.
Pitt is set to take on producer roles on the sequel to his zombie horror smash World War Z and TV drama Americanah. He will also serve as executive producer on The Underground Railroad, the big screen version of the novel The Curious Incident of the Dog in the Night-Time and a documentary about the late rock star Chris Cornell. But Pitt doesn’t seem too interested in appearing in front of the camera again any time soon.
Indeed, while Pitt is keeping busy behind the scenes, his acting schedule currently looks a little sparse. So why is one of the most bankable box office stars of his generation taking time out from the spotlight? Well, Pitt has hinted at the reasons in several interviews to promote Once Upon a Time… in Hollywood.
In a chat with Harry Smith of NBC, Pitt was asked whether he could relate to the downward turns that the two main characters in the Tarantino film were experiencing. He answered, “I think we’re all aware there’s a shelf life on this. But it’s really important to me the people I spend my time with and the artists that I respect.”
Pitt also showed just how self-aware he is during a chat with the Australian version of GQ magazine. Referencing his acting career, he remarked, “I keep doing less and less. I really believe that overall it’s a younger man’s game. Not that there aren’t substantial parts for older characters. I just feel, the game itself, it’ll move on naturally. There will be a natural selection to it all.”
And Pitt seems more than content with this natural selection. In fact, he also sees several benefits of aging in Hollywood. While on the red carpet of the 2020 Screen Actors Guild Awards, he told USA Today, “It’s amazing how much more relaxed you get the older you get, right?”
Unlike Pitt, DiCaprio hasn’t talked about taking his foot off the pedal when it comes to his acting career. The star is 11 years Pitt’s junior after all. However, he still accepts that he will now always be competing with Hollywood’s constant quest to find the next bright young thing.
DiCaprio told NBC, “You look at the trajectory, and the careers of some of the greatest actors that I’ve admired and they ebb and flow,” he said. “There’s good times, and there’s bad times, and hopefully you could just be in the race as a long-distance runner is the only hope – and not burn out.”
And although DiCaprio is still very much at the top of his game, he’s still well aware of how fickle the fame game can be. In an interview with ABC, he said, “I’ve grown up in this industry, I have a lot of friends that are actors… I know how hard it is to be successful in this industry.”
Referring to both himself and Pitt, DiCaprio added, “I think we both sort of instinctively understand that dynamic. That relationship of how isolating this industry can be being on sets months at a time disconnected from your family and friends. Those professional relationships kind of do turn into family they become everything to you while you’re there.”
In the same interview Pitt was also keen to point out that he and DiCaprio wouldn’t have careers if it all if it wasn’t for all the behind-the-scenes crew. He said, “To be able to do what we do there’s 100, 200, 300 people behind us all supporting this system and are hustling from job to job. And it’s perpetual, it’s continual and you know, it’s a job.”
DiCaprio also acknowledged how lucky he is in an interview with Deadline. He said, “I don’t know many stories of people of this industry where everything was immediately easy, navigating yourself through the industry. I grew up in this town, tried a lot to get into this industry when I was younger. I know who these guys are. I got my one lucky shot, and knock on wood, it went very well for me.”
“I do believe that opportunity presents itself at certain points in your life,” DiCaprio continued. “And it’s that old saying… you’ve got to be focused and prepared enough to seize those opportunities and be extremely lucky to be at the right place in the right time. You have to be ready and recognize those turning points in an actor’s life.”
Of course, despite the stars’ reservations, cinemagoing audiences still appear to be accepting Pitt and DiCaprio as leading men. Once Upon a Time… in Hollywood grossed more than $374 million worldwide, a figure that only Django Unchained surpasses on the Tarantino box office list. And the industry itself has also continued to shower them with accolades.
DiCaprio picked up the fourth Best Actor Oscar nomination of his career for his turn as Rick Dalton. The star had previously won for The Revenant and picked up nods for The Aviator, Blood Diamond and The Wolf of Wall Street. He was also recognized in the Best Supporting Actor category for his performance in What’s Eating Gilbert Grape?
Pitt, meanwhile, became hot favorite to pick up his first ever acting Academy Award for his supporting turn as Cliff Booth. The star had previously been Oscar- nominated for 12 Monkeys, The Curious Case of Benjamin Button and Moneyball. And he did share the Best Picture win for 12 Years as a Slave as a producer.