What Took Brad Pitt So Long to Have This Much Fun?

Brad Pitt, in a tux on the red carpet, looks at the camera with a slight smile.
Brad Pitt at the 77th Annual Golden Globe Awards at the Beverly Hilton Hotel in California on Jan. 5. Trae Patton/NBC/NBCU Photo Bank via Getty Images

Only in the past few years has Brad Pitt existed as a star without an equally famous woman by his side. And instead of rejecting the solo spotlight, of late he’s seemed to be playfully courting it. In recent weeks, he has joked about his “disaster of a love life” on Maron, quipped that Britain is newly single like him, and shown up at the Oscar nominees luncheon wearing a nametag. At the apex of a varied and scrutinized career, Pitt is grabbing headlines by taking his own public image for a joyride. You don’t say “any woman I stand next to, they say I’m dating” in your acceptance speech (ghostwritten or not) at the Golden Globes and then grasp the arm of the ex-wife you still share tabloid covers with unless you’re either a) up to something, perhaps squelching rumors or happy to ignite new ones of your own; or b) adjusting the minute calibrations that have largely governed your approach to playing the role of yourself. Or both. For a quarter century, Brad Pitt has been chafing at the constraints of “Brad Pitt”; if at the age of 56 he’s learning to collapse that distinction, the public seems ready to embrace the new Brad—as long as it buys the story.

One hesitates to say Brad Pitt is “back” because his fame has never ebbed, though his reputation—so warily managed for years—took a hit in his 2016 separation from Angelina Jolie. Instead of the family-minded humanitarian he’d been with her, he suddenly became legible as someone with addiction problems who might have raised a hand to his teen son Maddox. Angelina Jolie unquestionably “won” the divorce; her focus on the family won her the public’s sympathy. But America loves a (male) sinner who hits bottom and bounces back more than it loves a (female) saint. And Pitt’s 2017 repentance tour—which included a GQ profile that addressed his addiction issues and, obliquely, the incident that allegedly led Angelina Jolie to file for divorce—was vague enough to sustain that narrative. (The GQ spread included multiple shots of Pitt literally falling headfirst onto pristine sand dunes; the Icarus imagery couldn’t be clearer.) But something is shifting as the star moves into his haggardly handsome phase—a twinkly, knowing descent of sorts from his old Olympian heights. Two years later, Pitt has two new movies to promote, and he’s reportedly sober, looser, seemingly more playful about his own celebrity, and—this is key—single.

Triptych of Brad Pitt shirtless in Once Upon a Time in Hollywood, Fight Club, and Thelma and Louise.
Brad Pitt in Once Upon a Time in Hollywood, Fight Club, and Thelma & Louise. Photo illustration by Slate. Photos by Columbia Pictures, Twentieth Century Fox, and MGM.

That matters because male public images are much, much simpler to wrangle; Pitt has a lot more room to maneuver in than he would if he were presently linked to a female star who has a more challenging lane to walk. As Taylor Swift put it in the recent documentary Miss Americana, “The female artists that I know of have reinvented themselves 20 times more than the male artists.” She describes how hard it is for a woman to keep the public from getting bored of her: “Be new to us, be young to us, but only in a new way and only the way we want.” The conventional wisdom about Pitt has been that he defers to his female partner’s image. Maybe he did in recognition of this unfair dynamic; maybe he just found it easier to be in the passenger seat. Either way, it’s certainly the case that he adjusts his style and interests and blends chameleonlike into the women he attaches himself to. When he was with Gwyneth Paltrow, he had straight blond hair like hers. When he was with Jennifer Aniston, he grew honey-colored highlights. When Jolie wore her hair long and flowing, so did he, and when she slicked it back, he did too. Left to his own devices, Pitt seems to be experimenting with rueful self-disclosure in public while performing an extended cleanup tour. He’s on good terms with Aniston, the woman he wronged! He even pulled out of appearing at the BAFTAs at the last minute for “family obligations” (which the tabloid Sun reported involved a possible reconciliation with his estranged son Maddox). Brad didn’t even have to turn up at the BAFTAs; his acceptance speech (read by Margot Robbie) made headlines. It included the Brexit joke, a divorce settlement reference, a line on Prince Harry’s departure, even an amusingly informal “blah blah blah.”

Stars dream of the kind of positive press and public response Pitt has been getting. Part of what’s crowd-pleasing about his recent turn is that, despite some tells suggesting that Pitt is doing some Olympic-level Oscar campaigning, it feels refreshingly unfiltered. Pitt’s old celebrity playbook would’ve had him carefully controlling his face while watching Aniston onstage. The eruption of delight on both sides (and longing, some wondered hopefully) feels not just new but transgressive. It’s breaking the rules for how both have played this particular scandal-of-the-century game. Some things have always felt more authentically Brad, of course—his interest in architecture, the slight depressive edge (that appealingly hapless droop of his lower lip) that makes him seem like a secret sad boy putting on his sunny game face—but whatever this is, it’s new, and it’s more.

Pitt feels freshly accessible because of what we were used to getting, for so long—a clear caginess about the line between Brad Pitt the man and the characters he made famous. Indeed, the temptation to read Pitt’s films autobiographically is so overwhelming that his resistance to being so read is more than understandable. Early in his stardom, Pitt said that the character he most directly resembled was his breakout turn in Thelma & Louise, but many of his subsequent roles have made direct comparisons to his life almost too obvious to bother with. The Jolie-Pitts’ actual partnership was bracketed by Mr. and Mrs. Smith, which captured two people trapped in their roles finally getting to know each other and falling in love, and By the Sea, which featured a married couple in turmoil. In Snatch, he plays a goofball whose charm makes him easy to underestimate—he’s savvier than he looks, has a formidable power and also a drinking problem. In The Assassination of Jesse James by the Coward Robert Ford, Pitt plays a man who knows he can’t possibly live up to his own legend.

Pitt used to be more coy about echoes of this kind; he’d invite those comparisons in order to deny them. He collaborated with photographer Steven Klein on a photo shoot of him and Jolie as miserable 1960s suburbanites with five small children, but at the time was still denying they were in a relationship. The bizarre and striking set of photographs—which only exacerbated rumors that Pitt’s marriage to Aniston ended because he wanted a family and she didn’t—famously led Jennifer Aniston to observe “there’s a sensitivity chip that’s missing.”

Triptych of photos of Pitt and Gwyneth Paltrow, Pitt and Jennifer Aniston, and Pitt and Angelina Jolie.
Brad Pitt with Gwyneth Paltrow, Jennifer Aniston, and Angelina Jolie. Photo illustration by Slate. Photos by Ron Galella/Ron Galella Collection via Getty Images, Ron Galella Ltd./Ron Galella Collection via Getty Images, and Jeffrey Mayer/WireImage/Getty Images.

This is all to say that Pitt has been playing with his persona for a long time, but not always nicely, or kindly, or easily. Certainly not with this self-deprecating twinkle. The star’s attitude toward his own fame has been souring since his still-early Interview With the Vampire days, when he flirted with waitresses in front of reporters and threw a little shade at how Tom Cruise—a notoriously controlling presence on the set of that film—was handling his fame and his career. (“I tell you, the machine Tom runs is quite impressive,” he told Rolling Stone’s Chris Mundy for a 1994 profile that features him shirtless with long blond hair. “I wouldn’t want to live like that but still. … Listen, if you want to stay on top, you’ve gotta stay on top.”) In later years, as Pitt joined Cruise in the echelons of the obscenely famous, his affect bounced from denial to anguished gratitude to resigned acquiescence to depressive self-awareness. “What’s your angle?” he wearily asked Rolling Stone’s Chris Heath in 1999, when he was dating Jennifer Aniston. “I’m the guy who’s got everything,” he told him later. “I know. But I’m telling you, once you get everything, then you’re just left with yourself. I’ve said it before and I’ll say it again: It doesn’t help you sleep any better, and you don’t wake up any better because of it.”

Back then, Pitt took unflattering descriptions of his public image poorly. He got pretty angry with Heath when asked to respond to the widespread perception that the actor was dumb. Heath meant it as an image problem, but Pitt suspected there was someone with a grudge circulating the claim, and he couldn’t be talked out of it. He got angrier still when Heath suggested he hadn’t heard this rumor about himself because the people around him might just not tell him.

I don’t want to be put in the position where I have to defend my intelligence, because I’m not going to do it. … Why do you want to put that out there? We live in a fucking vacuum, man. What constitutes food for us has no place in the outside world, and that’s the bottom line.

This strange, unpolished moment in the Pitt annals is tantalizing because it betrays, among other things, the star’s frustration with—and confusion about—the insides and outsides that constitute his circles and his world since becoming famous. I don’t know what this means: What constitutes food for us has no place in the outside world. That it’s unedited and inaccessible makes it seem true.

Since his relationship with Jolie ended, Pitt has occasionally been more forthcoming about how he links his persona to his work. “I have so much attached to this façade,” he told GQ in 2017, gesturing at himself. He uses the same word—façade—almost immediately to refer to Glen McMahon, the character with a funny run who he plays in War Machine. The run to me was important because it was about the delusion of your own grandeur, not knowing what you really look like. All pencil legs, you know. Not being able to connect reality to this facade of grandeur.” The implication is obvious: Pitt is having a hard time connecting the indignities of being a real person to the grandiose image of himself. The ease of movement on-screen with which he’s rightly credited is real, but so is the difficulty he’s had inhabiting it offstage. Recent interviews are particularly clear about Pitt’s distaste for the story conventions that tend to plague leading men. “I could not get out of the middle of the frame,” he recently told the New York Times of playing Achilles in Troy. “It was driving me crazy.”

But when the Times asked him in that same interview whether he’s aware of how audiences might see his star identity resonating with a particular role, he replied—still! Improbably!—“The answer is no. I mean, I’m aware of when a director is using my persona really well. Fincher in Fight Club was twisting it. In Jesse James, it was pretty blatant. But no, I’m not really aware, and I’m not sure I should be.”

Pitt has been playing the role of himself for decades; whether he “should be” aware of how his persona is used and deployed is irrelevant. He simply is aware, and we know that because he’s frequently deployed it himself: He uses the story of and about his life to get public buy-in for things that matter to him. He and Jolie used their celebrity strategically, dragging paparazzi cameras with them to countries in crisis. (Jolie famously gave birth in Namibia with this aim in mind.) Pitt has used his star power to help smaller movies get made and marketed; by taking a smaller role or producing, he manages to get them exposure they might not otherwise have. He also used his celebrity to build houses after Hurricane Katrina. This effort was less successful: The sustainable homes Pitt’s Make It Right organization built for Katrina survivors were beautifully designed, but they’re allegedly falling apart now and plagued with mold, and the company, which allegedly made people sign nondisclosure agreements in exchange for getting settlements or repairs, faces a class-action suit. Persona-dependent do-gooding has its limits.

These days, he narrates himself less as a crusader and more as a solitary introspective sort who thinks a lot about fatherhood—all while, from the looks of it, campaigning as hard as he can for an Oscar and flaunting an experimental reconciliation of his private and public selves. He’s splashing around in the puddles of his own legend. This intense, varied, funny, full-on Brad-ness, in some ways, is a more natural fit for a guy whose laissez-faire Midwestern demeanor didn’t always comport with his past caginess, or with the defiant ambition of his younger and angrier career choices.

“You get older and you just get tired of protecting yourself or having any secrets. You know?” Pitt told Christiane Amanpour when she invited him to compare his mournful, trying-to-move-on character in Ad Astra to himself. “I mean we all carry, I think, great pains, great regrets. We’ve all experienced loss, we’ve all experienced great loneliness at times. And we’re good at packing that away, not dealing with it. Some are really good at getting through it and coming out the other side a more well-rounded, more confident and loving human being.”

It’s a series of sentences that could apply equally to the fictional role and the man behind it. The lachrymose tone of his 2017 headlines has given way to a comedic disregard for the guarded celebrity he used to pursue. And, if public acclaim is a measuring stick, it’s working for him. Brad Pitt is joking with the lads, hanging out with Leonardo DiCaprio, and making fun of everything and himself. A star, finally come down to earth, a bit looser, a bit more at home in himself, zipping up the gaps in his past with a combination of silliness and contrition. It’s a great solo act, one that very well might be strategic and cannily carried out. It also might be true.