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Now Presenting: Leo and Brad Watch

Leonardo DiCaprio and Brad Pitt have been making their rounds in advance of their upcoming Quentin Tarantino film, ‘Once Upon a Time ... in Hollywood.’ But are the older actors equipped to navigate the modern viral-moment-thirsty press circuit?

Getty Images/Ringer illustration

The Hollywood bromance is a timeless tradition, one that has seen a recent evolution when it comes to promoting films on social media and beyond. Marvel has perfected the goofy, instantly viral bromance—as seen most recently by Jake Gyllenhaal and Tom Holland on the Spider-Man: Far From Home circuit—but it’s something else entirely to watch older, more prestigious actors try to engage in this new world of viral bits and cheery banter.

Enter Leonardo DiCaprio and Brad Pitt, who are starring in their first film together in Quentin Tarantino’s Once Upon a Time ... in Hollywood. Would the usual curated profiles, glossy photoshoots, and perfectly groomed red carpet appearances be enough for the movie’s rollout? Or would the demand for Twitter-friendly moments and memes win out in the end?

A week out from the film’s stateside debut, it seems that they’ve struck a tenuous balance between the two strategies. And so, for all our grizzled A-lister content needs, I present Leo and Brad Watch, an ongoing collection of the best, most pained promotional moments from the Once Upon a Time ... in Hollywood press cycle.

May 21: Esquire reveals that Brad Pitt has no concept of time.

In late May, right before Once Upon a Time ... in Hollywood hit Cannes, Esquire released the first in-depth interview with Brad, Leo, and Tarantino about the film. It was full of annoyingly handsome photosets and predictable monologues from Tarantino, but what stuck out was the possibility that Brad Pitt and Leonardo DiCaprio have no real concept of time.

“We’re all ’90s babies,” claimed Leo in the profile—an objectively untrue statement! Leo was born in 1974, and Brad and Tarantino were born in 1963. “We all kind of came of age in this industry about the same time,” Brad says. Sure, Jan.

Later in the profile, Brad and Leo discuss the late Luke Perry, who filmed his scenes for Once Upon a Time shortly before his death in March. “I remember my friend Vinny, who is in the film as well, we walked in and we both had this butterfly moment of like, “Oh my God, that’s Luke Perry over there!,” said Leo. Brad agrees: “‘That’s Luke fucking Perry!’ We were like kids in the candy shop because I remember going to the studios and [Beverly Hills, 90210] was going on and he was that icon of coolness for us as teenagers.”

Teenagers? Brad Pitt was 27 years old in 1990, when a 24-year-old Luke Perry got his start on Beverly Hills, 90210. Is Brad confused, or is he just trying to pretend he isn’t 11 years older than his costar? Unclear. Either way, off to a great start!

May 22: Brad and Leo bro it up in Cannes.

Now this part they could do in their sleep.

Brad and Leo arrived in Cannes in full movie star mode for the photocall and premiere of the film looking good as hell. The shades? Flawless. The page-boy cap? Dashing. The increasingly graying stubble? Impeccable. And the actual red carpet event? Divine.

May 29: Brad is apparently exhausted by press cycle, takes a nap in a Venice riverboat.

Apparently Cannes was tough on Brad, because he took off to Venice to get some z’s at the end of May. Think a celebrity taking a nap in public isn’t a worthy news event? Think again.

June 25: Leo’s own vacation is a little more chaotic.

A month later, Leo took a page out of Brad’s book, escaping to Malibu before the promo cycle amped up again. But his vacay wasn’t quite as relaxing—during a beach volleyball game with girlfriend Camila Morrone and Robin Thicke (sure!), Leo took a ball right to the face.

It’s not the first time Leo’s had a volleyball mishap, and it won’t be the last. Personally, I’m grateful.

July 12: Leo and Brad realize they both started on Growing Pains, and Brad still has no idea how old he is.

A quickly established talking point for Leo and Brad was the fact that they both started their careers on Growing Pains, though they didn’t cross paths on the sitcom. Or did they? (They didn’t, but Brad clearly has no idea.)

“’89, ’90,” Brad says in a Today Show interview, pointing to himself and then Leo to reference when they each appeared on the show. “I’m ’91, ’92,” Leo corrects. “Oh, were you?” Brad replies. “Maybe I was ’90 then.” Leo gives up: “I don’t know, we’re talking decades ago.” If you’re going to tell this story multiple times, figure out the dates, my guys! Brad, please buy a calendar.

July 15: Leo is horrified by his costar’s cinematic interests.

The age dynamic between Brad and Leo is made even more confusing when Margot Robbie joins the picture, as seen in a recent interview with all three on MTV News. When asked what movie they’d be ashamed to admit they’ve never seen, Brad says Gone With the Wind, and Leo loses his mind.

I can’t help but wonder whether Leo reacts the same way when his very young girlfriends admit their own cinematic blind spots. If he’s assigning Margot film studies homework, has Camila Morrone gotten the same treatment? How many times has he made her watch Citizen Kane?

Leo was less inclined to comment on his own film history, however—MTV then asked the trio to rule on the age-old question of whether there was enough room on the door at the end of Titanic, and Leo clammed right up.

“No comment” does not make for a viral moment, Leo. Do better!

Stay tuned for more Leo and Brad Watch leading up to Once Upon a Time ... in Hollywood—we’re still missing a truly iconic quote or gif-able moment from at least one of them.