When Brad Pitt Met Leonardo DiCaprio: How the Last Two Movie Stars Finally Came Together for Once Upon a Time in Hollywood

It only took 30 or so years for this pair of Tinseltown's few remaining marquee names to share the screen.

By Billy Nilles Jul 26, 2019 10:00 AMTags
Brad Pitt, Leonardo DiCaprio, How the Last Two Movie Stars Finally Came TogetherGetty Images; Sony Pictures/E! Illustration

There are very few movie stars left in Hollywood.

With an industry that generates nearly all of its business on the back of marketable franchises, be they of the animated, superhero or Disney live-action adaptation variety, chock full of interchangeable actors and actress who spend much of their time inside the costume of a character more famous than they'll ever be, it feels as though there's simply no place for them any more. Long gone are the days when a movie could exist, let alone rule the box office, solely off the wattage of its top-billed actors.

And in an age where social media influencers carry more clout with certain subsets of the movie-going audience than most actors could ever dream of—if those movie-goers are even, you know, going to the movies anymore—the sun seems to be setting on the era of the movie star. Hell, with four of his last five movies being franchise installments, even Tom Cruise has given in to the new world order.

But like we said, there are still a few left. And at the top of that shrinking list, almost all by their lonesome, stand Leonardo DiCaprio and Brad Pitt

What Leonardo DiCaprio Has Learned About Brad Pitt

As two of the final few vestiges from the golden age of the movie star, a time before the swirling confluence of social media, a lack of interest in movies that aren't just adaptations of properties that'll succeed regardless of who's starring in them, and a generation that simply seems disinterested in any form of legacy media made them a dying breed, Pitt and DiCaprio have successfully pulled off what few of their contemporaries. They've not only managed to keep their heads above water, but they've proven that they are still box office draws whose work and personal lives people continue to care about—a duality necessary to be considered a true movie star. And they've done it without turning to the franchise machine that's ensnaring everyone just looking to get by in this new age of cinema. (Even Pitt's ex-wife Angelina Jolie has doubled down as she navigates her own career, returning in Disney's Maleficent: Mistress of Evil this fall before she joins the ever expanding Marvel Cinematic Universe with a role in 2020's The Eternals officially confirmed last weekend at San Diego-Comic Con.) DiCaprio alone has generated nearly $3.3 billion in global box office revenue with his 10 most recent films, as tabulated by The Hollywood Reporter.

With the July 26 release of Once Upon a Time in Hollywood, director Quentin Tarantino's love letter to a time in Tinseltown not unlike the one we find ourselves in now, where established actors found the ground rapidly shifting beneath them and their futures thrown into question, these two supernovas join forces for—if you can believe it—the first time in their thirty-plus year careers.

David Fisher/REX/Shutterstock

It's not that there haven't been run-ins between the two in their personal lives, however—Hollywood is a small world, after all, and Pitt's former flame Gwyneth Paltrow (with whom he dated from 1994 to 1997) did, in 2013, credit DiCaprio with planting the seed for her vegetarianism 20 years prior, lending credence to the idea that the two men were traveling in similar circles in the early days of their career—or near-misses in their professional ones.

Both actors did some of their earliest work, coincidentally, on the ABC family sitcom Growing Pains. Pitt guest-starred in two episodes, one in 1987 and the other in '89, playing two different characters, while DiCaprio recurred in the 1991-92 season as Luke Brower, the homeless boy taken in by the Seaver family.

"We did start on the same television show," Pitt told Today's Harry Smith during an interview alongside Tarantino and his co-stars DiCaprio and Margot Robbie earlier this month.

"I mean, we're talkin' decades ago," DiCaprio added.

And while their careers would take off from there, propelling them to an echelon of stardom most only ever dream of as they ruled the box office in films like Seven and Mr. & Mrs. Smith for Pitt and Titanic and Catch Me If You Can for DiCaprio, they each traversed the road of the movie star in ways all their own.

Pitt would hop from one high-profile relationship to the next, seemingly relishing his power couple status whether it was Paltrow, first wife Jennifer Aniston or second wife Jolie on his arm, before settling into the role of doting dad with his and Jolie's impressive brood, while DiCaprio has lived a bit of a playboy life, always linked to one model or another, while doing his best to steer focus away from who he's sharing a bed with. (He's notoriously tight-lipped about nearly all facets of his personal life.)

See How the Stars of Once Upon a Time in Hollywood Compare to the Real-Life Players

Both have found their passion projects, with DiCaprio devoting much of his time and status to environmental activism—he launched the Leonardo DiCaprio Foundation, devoted to promoting environmental awareness, all the way back in 1998—while Pitt, an avid architecture enthusiast, has worked to provide sustainable, affordable housing in areas in need.

Pitt eschews all social media—"Life's pretty good without it," he told E! News' Justin Sylvester when asked if he'd consider creating an Instagram account at the Once Upon a Time in Hollywood premiere this week. "I don't see the point"—while DiCaprio leverages his impressive follower tally (19.1 million on Twitter, 32.9 million in IG) to raise awareness for the global climate crisis.

DiCaprio approaches his roles with a studied intensity, pushing himself past the breaking point in films like The Revenant, which saw him fight a bear and finally won him an Oscar, while Pitt imbues his characters with an enviable amount of chill.


But despite the different ways each have approached their parallel tracks on the stardom express, it's the fact that they were both on those very tracks that bonded them almost immediately when Tarantino decided to re-team with his Inglorious Basterds and Django Unchained stars, pairing them as declining star of TV westerns Rick Dalton (DiCaprio's role) and his longtime stunt double, Cliff Booth (Pitt, naturally). 

"You come to Hollywood and you're basically isolated and left to your own devices," DiCaprio told The New York Times back in May. "[Rick and Cliff] rely on this friendship for everything. We immediately fell into those shoes. We understood that relationship [laughs] so quickly that on the first day, we were those guys."

As Pitt explained to the newspaper, it was their shared experiences that bonded them so quickly. "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," he said. "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. And, you know, my friend here [he gestures toward DiCaprio] has been the same. 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."

Brad Pitt Awards Leonardo DiCaprio With "Best Meltdown" for Once Upon a Time in Hollywood Scene

It's also what convinced Tarantino that each was perfect for their role.

Of his decision to cast Pitt as the stunt man, the director told GQ Australia this month, "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. Like a Steve McQueen or someone – you like watching him. You like watching the way he moves, you like watching the way he drives. This cool, masculine quality that a movie star can have – he has it. And he's had it for this whole last generation of actors."

And for DiCaprio, while it took some serious convincing on the actor's part to land him the villainous role he played perfectly in Django, Tarantino told The Hollywood Reporter that no such convincing needed to take place this time around. At least, not on DiCaprio's end. "I absolutely had him in mind, but I didn't know if I was going to get him," the director remarked. "I'm not presumptuous. I mean, everyone in the world wants him."

Kevin Winter/Getty Images

While both Pitt and DiCaprio have gushed about how working on the film allowed them the opportunity to work with late greats like Luke Perry, who pops up as actor Wayne Maunder in what would tragically be his last film role after passing away following a massive stroke, and Burt Reynolds, who was all set to play a pivotal role in the film before passing away during rehearsals, it also allowed them the opportunity to work together at long last. And it seems that, through the experience, a bromance has blossomed.

(It's here that we should note that DiCaprio and Pitt have both appeared in a commercial short film directed by Martin Scorsese in 2015 entitled The Audition, meant to promote the Studio City Macau resort and casino. In the film, DiCaprio and Robert DeNiro play themselves, competing for a role in a Scorsese film, but when they see the director meeting with Pitt, they give up the fight and go to the resort's spa. Pitt and DiCaprio exchanged no lines of dialogue in the piece.)

Once Upon a Time in Hollywood Premiere: See Every Look as the Stars Arrive

"He's not only made great choices as an actor, not only is he extremely talented, but he's [also] incredibly easy to work with and that's the dynamic that I think both of us needed in this film," DiCaprio told E! News at the film's premiere of working with Pitt. "We needed to have guys that implicitly knew this town, knew this industry and knew this type of relationship of, you know, guys that are professionals but then become family."

The comments echoed what DiCaprio told reporters during the film's press conference at this year's Cannes Film Festival in May. "Brad is not only a terrific actor, but he's a professional. 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. And I think we together forged, hopefully, a great cinematic bond in a film about our industry together."

And while Pitt joked with Extra about the reason why he'd only just worked with DiCaprio now—"Yeah, I had a restraining order against him for a while... incident in '94 we don't like to talk about," he told the outlet at the film's premiere with a laugh—he's been equally effusive about his time spent with his co-star.

"It was really great ease and really great fun," Pitt said while at Cannes. "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."

In fact, the two have gotten along so well that there's even gossip about the pair spending their free time together since filming wrapped. According to The Sun, DiCaprio and Pitt bonded over a shared appreciation of pottery, with a source telling the UK outlet, "Brad's got his own sculpting studio at his house and Leo loves coming over to use it. They sometimes hang out with Brad's artist pals, but other times it's just the two of them."

"Leo brings sandwiches over from their favourite place, Fat Sal's," the source continued, "and they spend their boys' nights creating art until the early hours."

While we're not sure sure we buy this delightful story, we do know that there's at least a glimmer of hope that this joining of forces between the two cinematic champs won't be a one-time thing.

Despite Pitt's recent admissions that he feels himself aging out of the industry—"I keep doing less and less," he told GQ Australia. "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"—he's also expressed a keen desire to team up with DiCaprio in the future.

"We have kind of the same reference points, we came on at the same time, have similar experiences to laugh about and I hope we get to do it again," he told reporters at Cannes. "It was great fun."

Hopefully they won't keep us waiting quite as long this time.

Once Upon a Time in Hollywood is in theaters now.