Inside Leonardo DiCaprio and Brad Pitt's Decades-Long Bromance

While they’ve technically only starred in one movie together, Leonardo DiCaprio and Brad Pitt’s friendship has been going strong for decades. Both the Once Upon A Time in Hollywood co-stars got their start in the same TV sitcom, and ran in the same circles before their 2019 appearance in the Quentin Tarantino-directed film, which also featured Margot Robbie and Austin Butler. Once these BFFs starred in the same movie, however, their bromance was taken to the next level.

In addition to raving about each other and their “pretty automatic” friendship during interviews and red carpet appearances, DiCaprio and Pitt have invested in their relationship off the Hollywood circuit. The “partners in crime” even have (pretty intimate) nicknames for each other, and regularly hang out to make pottery and eat sandwiches together. Talk about bro goals.

From crossing paths throughout the years (including the little-known project they starred in together before Once Upon A Time in Hollywood) to becoming besties who pump each other up on and off the red carpet, here’s a look back at DiCaprio and Pitt’s friendship timeline.

1980s/1990s: Both DiCaprio and Pitt start their acting careers on the same TV show

The Killers of the Flower Moon actor and the Babylon star revealed that they broke out into Hollywood in the same ‘80s sitcom – Growing Pains – although they missed each other by a few years.

In a July 2019 interview promoting Once Upon A Time in Hollywood on the Today show, Pitt shared that they’d discovered their unlikely connection. “We did start on the same television show,” he said, to which DiCaprio chimed in, “I mean, we’re talking decades ago.”

Pitt appeared in two episodes of the ABC sitcom in 1987 and 1989, while DiCaprio played Luke Brower from 1991 to 1992.

September 1995: DiCaprio and Pitt pose for photos in the early Noughties

The A-listers were both part of the Hollywood elite in the early 2000s; DiCaprio’s star power was only growing from his roles in Titanic, Aviator, and The Departed, while Pitt was enjoying his post-Fight Club fame and filming the Ocean’s franchise movies, Troy, and Mr. & Mrs. Smith. 

It’s unclear exactly when the stars were introduced – there are a few photos of them at events in the late '90s and early 2000s – but Pitt said their friendship was “pretty automatic,” in part due to their similarities.

“We both came on the scene around the same time, we have crossed paths many times, we have the same reference points,” he told The New York Times about their history in a May 2019 interview. “We have mutual respect and I know when an actor elevates a scene, so we carry that respect.

2015: DiCaprio and Pitt both appear in Martin Scorsese’s $70 million short film together

Fresh off his Wolf of Wall Street success, DiCaprio teamed up with Scorsese once again for what was then rumored to be the most expensive commercial ever made. The Audition – which was an ad for City of Dreams and Studio City casinos in Manila and Macau – showed DiCaprio and Robert DeNiro duking it out after they realized they’d both been called to audition for the same role. However, at the last minute, Pitt swooped in to steal the part.

June - November 2018: Filming for Once Upon A Time in Hollywood takes place

Pitt and DiCaprio, along with co-stars like Margot Robbie, Margaret Qualley, Austin Butler, and Luke Perry, headed to Los Angeles to recreate the summer of 1969.

May 22, 2019: DiCaprio and Pitt  pose with their arms around each other at Cannes

"It was really great ease and really great fun," Pitt told reporters about working with DiCaprio at a Cannes press conference, per Us Weekly. "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."

The feeling was mutual, as DiCaprio also raved about the “terrific comfort and ease” he had working with Pitt.  “We kind of grew up in the same generation, got our start around the same time,” he said, calling Pitt “not only a terrific actor, but a professional.”

“I have to say it was incredibly easy — incredibly easy working with Brad,” he said. “And I think we together forged, hopefully, a great cinematic bond in a film about our industry together.”

That same day, the Django Unchained told The New York Times that the pair’s friendship had some similarities to that of his and Pitt’s characters in the movie.

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

July 2019: Pitt calls DiCaprio “great fun” in an interview

Pitt opened up about their friendship off-screen and what it was like working together with DiCaprio in a July interview with GQ, saying, "We kind of popped at the same time."

He also shared his admiration of his co-star’s talent, adding, "This is a guy who's really giving and really goes for it, so you know it's great fun being able to spar with that caliber of actor. And he's just great fun."

July 22, 2019: Pitt quips that a “restraining order” was the reason the two hadn't previously worked together at the Once Upon A Time in Hollywood’s LA premiere

The Inglorious Basterds star was all jokes while walking the red carpet at the LA premiere for his new movie. When asked about working with DiCaprio, he quipped, "He's a good egg, and I'm really happy the restraining order was lifted off of me, so we were able to work together.”

“No, he's a great egg,” he continued. “We come from the same circles and I really admire his taste and his choices. I'm really happy this one lined up for us."

The Oscar winner couldn’t resist teasing what audiences could expect from DiCaprio’s performance. "His character in this is hilarious," he added. "He throws one of the best tantrums ever laid down on film."

DiCaprio also talked about his relationship with Pitt on the red carpet, reiterating how easy it was for them to relate to their roles. “We both live in Los Angeles and this is about the changing of the culture in the late '60s, and we understand these dynamics of these professional relationships that also turn into families," he said.

Also July 22, 2019: Reports claim that DiCaprio and Pitt enjoy making ceramics together

A source told The Sun that the real-life best friends enjoy “boys nights” while taking part in one of Pitt’s favorite hobbies: making sculptures.

"Brad's got his own sculpting studio at his house, and Leo loves coming over to use it," the source reportedly told the publication. "They sometimes hang out with Brad's artist pals, but other times it's just the two of them.”

The source also suggested that the actors have a go-to place where they like to eat together.  “Leo brings sandwiches over from their place, Fat Sal's, and they spend their boys' nights creating art until the early hours,” they added.

Pitt previously opened up about his love of sculpture and how getting into the art form helped him heal after his divorce from Angelina Jolie.

“If I'm not creating something, doing something, putting it out there, then I'll just be creating scenarios of fiery demise in my mind," he told GQ Style in 2017, revealing that he’d been wanting to get into the hobby for 10 years.

“I'm making everything. I'm working with clay, plaster, rebar, wood. Just trying to learn the materials,” he added. “You know, I surprise myself. But it's a very, very lonely occupation. “

July 26, 2019: Once Upon a Time in Hollywood comes out

Tarantino’s highly-anticipated film was released to rave reviews from critics and viewers alike, who lauded the movie for its depiction of the golden age of film.

“What was entirely unexpected was that Once Upon a Time... in Hollywood would be such a moving film,” The New York Times wrote, “at once a love letter – and a dream – of the Hollywood that was.”

January 2020: Pitt reveals his nickname for DiCaprio during his Golden Globes speech shout-out

When the World War Z won the Golden Globe for best supporting actor in a motion picture, he called out his “partner in crime” during his acceptance speech. 

"I have to thank my partner in crime, LDC," he told the crowd. "Before The Revenant, I used to watch year after year his costars 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." He concluded his shout-out by poking fun at a popular debate from DiCaprio’s film, Titanic: “Still, I would have shared the raft,” he joked.

January 2020: Pitt hilariously shares DiCaprio’s nickname for him

On the red carpet at the Screen Actors Guild Awards, Pitt told People that DiCaprio calls him by a “confusing” moniker. “Lover. He calls me Lover,” Pitt said, explaining, “It’s a bit confusing, but I roll with it.”

He also talked about his “pretty easy” onscreen chemistry with DiCaprio, sharing, “You’ll find, with most of the guys, I would say we’re all pretty much rooting for each other, we all have respect for each other, we all have a good laugh with each other, and it plays.”

February 9, 2020: Pitt also calls out DiCaprio during his Oscars acceptance speech

While accepting an Oscar for best supporting actor, the Seven actor gave his co-star another hilarious awards season nod.

"Leo, I'll ride on your coattails any day, man,” he said during his speech. “The view's fantastic."