How Leonardo DiCaprio Gets Away With It

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What is it with our affection for famous actors who don’t want to be famous actors? It’s a unique kiss of reputational death for a public figure to be too interested in being a public figure. The more an actor eschews public affection, the more affection we have for him—Cillian Murphy, for example, now promoting his Netflix movie Steve, is making a meal out of hating public attention as a part of the movie’s promotional cycle. But has anyone been more famous and yet less entrenched in fame than one of the most celebrated actors in the world, recognizable even by a nickname, an undeniable face since he was a kid wearing flannel and denim on ’80s shows? No one hates and therefore courts fame quite like an actor with no real interest in it, and Leonardo DiCaprio has, for his entire career, remained dutifully disinterested in a main part of the gig.

You know him already: delicate hairless jaw in the ’80s and ’90s, hair falling effortlessly over his forehead like Tuxedo Mask’s, Siberian husky blue eyes, lips lightly pursed as if he has a secret (the secret is he knows you want to fuck him). For Gen X and elder millennials, DiCaprio was the blueprint for an attractive straight white man, someone sensitive enough to get you to cry with him in Romeo + Juliet but still masculine enough to make you clench your jaw with desire when he danced with Rose in Titanic. Even going back to 1998, Seventeen magazine labeled him “the reluctant Romeo” in their cover story, right after Titanic came out and made nearly $53 million domestically at the box office on its opening weekend. Former co-stars, casting directors, magazine editors, hairstylists, and crew members waxed poetic about DiCaprio’s dual charm and inconspicuousness. “He’s one of those young men who doesn’t want to be a movie star,” a casting director told the magazine. “He really wants to be known for his acting, not for his looks.” Kate Winslet called him “the world’s most beautiful-looking man, but yet he doesn’t think that he’s gorgeous.” Alan Thicke called him a “cutup, clown, and lighthearted free spirit” on the set of Growing Pains. An old teacher called him “disruptive in a charming way.”

“What’s his secret?” Seventeen asked when DiCaprio was just 23. “Leonardo is a thinking, sensitive girl’s heartthrob. He exudes a vulnerability that girls crave.”

Now 50, DiCaprio has had the kind of career trajectory most overly buff male leads could only dream of: child star to teen heartthrob to prestige-drama actor to climate activist, all while remaining mostly scandal-free. Through it all, DiCaprio has somehow maintained a game audience of Scorsese-heads and squealing 42-year-old girl-women with a decades-long crush. People want to see his movies and root for him at the Oscars. DiCaprio is no stranger to awards-bait, and his latest movie, One Battle After Another, is premiering to rave reviews. Even the lesbians love him.

But take a closer look at his more recent record, and DiCaprio starts to get a little slimy. At his big age, he seems pathologically incapable of dating a woman older than 27. His filmography remains pretty unimpeachable, but his record as a climate activist is a joke; lately, he’s been spending time on megayachts with Jeff Bezos and Lauren Sánchez. (Much like Katy Perry, fellow Bezos friend and bleeding-heart Democrat, DiCaprio stumped for Kamala Harris while Bezos killed op-eds in the Washington Post supporting her presidential candidacy.) His relationships with the uber-rich go well beyond the founder of Amazon—his friendship with fugitive businessman Jho Low landed DiCaprio in at least one deposition. His latest business stunt is his co-financing of a luxury hotel near Tel Aviv, one being built not too far from an active genocide.

Leo might be the last true Gen X star, someone who’s managing to get away with it all. He’s an untouchable Hollywood actor who only works on the most impressive prestige projects with select directors, and who can fuck around without ever seeming to find out. Fellow big-time movie stars like Tom Cruise and Johnny Depp and Brad Pitt have incurred some light reputational damage, either for rumors around their own cultish behavior or allegedly abusing their wives or children. But DiCaprio has evaded almost all criticism, and almost all retribution. His hypocrisy is noted, but never really held against him. While other famous people have all been raked over the coals for their participation in the Sánchez-Bezos wedding (all women, no less), DiCaprio skated on by from behind a black baseball cap.

How does he manage to get away with it all? Is he just the right age—and perhaps the final age—for an actor who can double-dip as both a pious liberal and a member of the indulgent class? Are his movies actually just that good? Or is there something pleasing for us, as a rapt audience, in watching a guy be an Actor’s Actor without being all that harmful or annoying? Our Overton window for bad male behavior has moved so much in the past decade; is it so bad that this 50-year-old multimillionaire has a penchant for dating women barely old enough to rent a car?

Child stars come in a few forms, but DiCaprio is the luckiest version of them: no drug scandals, no noisy affairs, no children, no marriages, no divorces. Born and raised in Los Angeles in the mid-’70s, he started acting in commercials like this ’80s-era ad for Bubble Yum and this one for Kraft Cheese as a kid. DiCaprio wasn’t a child star in the way we think of it now—a kid crowded by a parent pushing him to make YouTube shorts or to become an influencer, though his high school drama teacher said his mother was “determined” to make him “a famous television and movie star.” In the early ’90s, he was cast as yet another precocious kid on ABC’s Growing Pains before getting the first of several lucky breaks, when he was cast alongside another Tiger Beat fixture, Johnny Depp, in What’s Eating Gilbert Grape. His role, as the intellectually disabled son of a physically disabled woman (a movie unlikely to be made today), got him his first Oscar nomination when he was still just a teenager.

But oh, nothing turned DiCaprio into “Leo”—a household name said, ideally, with a heavy, yearning, virginal (for me, at least) sigh—quite like his 1997 role as Jack in Titanic. In one movie—back when he was still an unknown, and when a three-hour movie about a boat by James Cameron was considered a huge gamble—he rewrote the rules of what a leading man should be. He lacked the punchable jaw or heaving pecs of an action star of the era, and instead made audiences fall in love with a gentler version of a man. “DiCaprio, 23, doesn’t have the size or muscled body of most movie heroes; he’s very young, slender, even rather delicate,” read New York magazine’s review. “DiCaprio’s cockiness is completely engaging (there’s a fundament of gallantry and decency in it).” Review after review of Titanic called DiCaprio “feminine,” not said as an insult but more with bewilderment. Male reviewers and audiences seemed to be wondering out loud: Women like this? 

Letting go of that flotsam and drowning in the Atlantic Ocean was the first in a career of stellar role choices. In fact, DiCaprio has hardly ever done a bad movie; since Titanic’s release almost 30 years ago, he has acted in 22 movies, and there’s not one true bomb among them. Catch Me If You Can, The Departed, Gangs of New York, The Wolf of Wall Street, Django Unchained, The Revenant, Once Upon a Time in Hollywood—DiCaprio has perfected the role of an unforgivable, highly suspect, morally duplicitous man either at the height of his power or at the nadir of his competence. In this clear way, DiCaprio has set himself apart from other actors around his age: He makes good movies that people want to see, and that reviewers want to lavish praise upon.

But he also picks characters with clear, unmistakable rot, and surely opposites attract even in art. Could someone actually evil play a slave owner in Django Unchained? Could a real liar be so good at playing a master con artist in Catch Me If You Can? DiCaprio has never been more pathetic than when playing a mostly ignored scientist who eventually cheats on his very nice wife with a cruel television news anchor in Don’t Look Up; at the same time, he was dutifully unmarried and doing whatever the fuck he wanted because he could. His characters are often morally compromised (Blood Diamond) or delusional (Shutter Island) or despairing beyond repair (Inception) or terrified (The Departed). Only sometimes do they get catharsis, and only in a cruel way: His character in Catch Me If You Can gets to work with the FBI, but not before losing everything he scammed so hard to get. His character in Gangs of New York kills and steals in order to maintain dominance. His character in Don’t Look Up dies, alongside everyone else. He’s such a good actor that DiCaprio doesn’t just feed into the myths about these characters (like the scammer with a heart of gold in Catch Me If You Can), but into the mythos around himself, too.

He’s rarely in comedies or romances—unless you count Don’t Look Up, which was more of a horror movie that continues to be a little too prescient about our current moment—and he frequently works with the same prestige directors over and over again. Six movies with Martin Scorsese, two with Quentin Tarantino, two with Baz Luhrmann, and one each with Steven Spielberg, Christopher Nolan, and Paul Thomas Anderson. It’s a page taken, it seems, from actors a decade DiCaprio’s senior: Brad Pitt, George Clooney, Tom Cruise. The bigger the movie star, the more he returns to the same director, creating a canon that speaks not just to creative interests but the stories the actor wants to tell. DiCaprio isn’t a mere participant in a movie, he’s a co-conspirator. He’s no longer a mere actor: He’s a director of our culture.

There is also an adroitness in the projects DiCaprio picks. He’s unflinchingly sincere in his performances, and he picks projects that demand such earnestness and good faith. In his latest movie, One Battle After Another, he plays a washed-up former revolutionary, out of whack and out of shape, now tasked with saving his teenage daughter from ruthless enemies. “DiCaprio is a perfect vessel,” the Atlantic wrote in their review. “He’s still plausible as the youthful action hero of the first chunk of the film, but he’s also loaded with pathos and expert comic timing.” It’s an underrated tactic for getting people to be more interested in your work than your sometimes-lurid personal life: Don’t shit where you eat, and be really good at your job.

You know the old joke, right? Leonardo DiCaprio gets older, but the girls he dates stay the same age. For the past 30 years, he’s been linked to women in their mid-20s while he’s aged his way into an AARP membership. In the ’90s, there were models like Naomi Cambell and Amber Valletta. In the early aughts, there were models like Gisele Bündchen and Bar Refaeli. In the 2010s, there were models like Erin Heatherton and Kelly Rohrbach. These days, he’s dating Italian pharmaceutical engineer Vittoria Ceretti. (Just kidding: She’s a model.)

Before Ceretti—who is a decrepit 27 years old—there was the Leo 25 Rule, since it seemed he had an age limit for who he’d date, capped at a tender 25. It’s even a joke within Hollywood circles. When Sabrina Carpenter turned 25 in 2024, she blew out candles on a cake with DiCaprio’s face on it alongside the caption from a meme about him: “Nooo don’t turn 25 your so sexy aha.”

There’s nothing inherently wrong or duplicitous about DiCaprio’s dating life. In fact, he seems to have taken a page out of the pre-Amal Clooney handbook: Make good movies, and enjoy your flavor(s) of the week. The women he dates, though young, are consenting adults, and there are virtually no substantive rumors about cruelty, abuse, unkindness, or even indifference between him and the women he courts. DiCaprio isn’t a pervert, just a cad, and a mostly traditional one: His version of womanizing is more reminiscent of early Hollywood tomfoolery than sexual manipulation. It’s almost a relief for an exhausted female audience to be able to enjoy a lightly slutty man without worrying too deeply about his secret malfeasance. You want to hurt a 45-year-old straight woman’s feelings? Tell her DiCaprio just got #MeToo’d.

Even if DiCaprio is a quasi-famous lothario, it’s still hard to track his personal romantic history with the sincere excellence of his artistic work. There were several members of the “Pussy Posse” in the late ’90s—that is, the group of young men running around Hollywood back then, as coined by New York magazine—who seemed perfectly suited to the gang. Kevin Connolly, who would later star in Entourage, and exhausting magician David Blaine were unofficial members, and yes: That makes sense. But DiCaprio’s participation is but a tidbit in the grand story of his celebrity. Now he’s the guy who won an Oscar for that bear movie instead of being the top-ranked Pussy Posse member.

In his romantic exploits, DiCaprio may have the most in common with Jack Nicholson than with any other male actor of the past 50 years. Notorious for being a Hollywood bachelor, Nicholson also spent most of his life single but in the company of much younger, very beautiful women, like Lara Flynn Boyle or this host of nameless, supine models on a boat in the south of France in 2009 when he was 72 years old. Publicly known as a very single, very horny old man, Nicholson got away with it by being insanely charismatic—go watch him in 2003’s Something’s Gotta Give and tell me you don’t want to fuck him, you coward!!!—but also by refusing to answer any questions about it.

What also helps re-create his mythos is that DiCaprio too eschews most press. The closest we get are a few weeks around the release of a new movie, but his interviews hew tightly to the topic at hand. More often than not, DiCaprio is busy highlighting his female co-stars, like he did in countless interviews with Lily Gladstone to promote Killers of the Flower Moon.

And in that prestige, Leo stays safe, not just from too much incisive critique about his personal life, but from the degradation of his public brand, his public image, and his public perception as a real actor. He doesn’t do many domestic advertisements, save a few ads for luxury cars or Rolexes, or some old Japanese credit card spots. Any brands he associates himself with are highbrow enough that it boxes out the average consumer anyway. Meanwhile, you’ve never seen a DiCaprio tweet or Instagram post, a podcast series or a newsletter. He’s staunchly offline, and so we only hear from him through his work and a few errant tabloid stories.

It’s a tale as old as Hollywood glamour! He’s just having fun, and who does it hurt if we have fun with him?

In 2016, DiCaprio talked about climate change during his Oscars acceptance speech: “Climate change is real,” he said. “It is the most urgent threat facing our entire species, and we need to work collectively together and stop procrastinating.” DiCaprio has spent much of his adult career lending his name to environmental missions, like in the late ’90s when he founded the Leonardo DiCaprio Foundation. (The organization continues to be referenced by other climate groups, but it’s unclear what it does exactly.) What DiCaprio mostly employs is his star power, to bring attention to droughts or deforestation. Within the confines of the attention economy, he often uses the keen interest in him well. Remember when Ryan Gosling went to the 2005 MTV Movie Awards in a T-shirt that just said “DARFUR”? That move was, spiritually, all Leo.

But nearly 10 years after DiCaprio made that speech at the Oscars, his record in climate activism would take a public and obvious hit. Earlier this year, he was seen covering his face with his omnipresent black baseball cap on his way to the opulent, wasteful, and disruptive wedding of the third-richest man in the world. Few are taking their daily cues on climate change from famous actors, but it certainly reeked of a particular kind of hypocrisy.

Plenty of celebrities were criticized for attending Jeff Bezos’ wedding to Lauren Sánchez, not least because Bezos had been so instrumental in Donald Trump’s reelection. The wedding was a vivid display of an oligarch’s climate selfishness; Bezos has long considered himself a climate activist, too, while also causing direct harm to the environment. In 2023, Bezos and DiCaprio entered the Protecting Our Planet Challenge, wherein a $200 million donation in partnership with the Brazilian government was earmarked to help achieve zero deforestation in the Amazon. It certainly didn’t seem to work: The next year, a University of Maryland study said 2024 was the worst year for deforestation around the world thus far. Meanwhile, transportation pollution wrought by Bezos’ Amazon has surged.

Still, it wasn’t DiCaprio who received the lion’s share of criticism for joining Bezos on his wedding blitz, even as he’s put both his money and his mouth on the line for climate change reform. Instead, it was mostly women: Oprah, Gayle King, Katy Perry, the Kardashians. Female celebrity is oft held to account more than the men are, but somehow, DiCaprio’s glaring hypocrisy was hardly considered. Why would Kim Kardashian owe us more moral clarity around Bezos’ brand of brutalizing capitalism than the guy who invested in two different cell-based meat companies?

DiCaprio was similarly Teflon-like when he got wrapped up in the investigation around Malaysian billionaire (and now, fugitive) Jho Low. In the spring of 2023, DiCaprio testified that Low had plans to donate millions of dollars to Obama’s 2012 campaign—which is, of course, very illegal for a foreign entity to do. But Low threw his money around DiCaprio in a few ways, including toward his charitable organizations, and in helping fund The Wolf of Wall Street. One New Year’s Eve, Low flew DiCaprio and a group of others between Australia and Las Vegas so he could celebrate two new years in one night.

But DiCaprio’s involvement with a billionaire’s scam didn’t mar much of his reputation. Frankly, none of his personal life choices or charity work or famous friends have changed his box-office bankability or his likeability.

It remains to be seen if DiCaprio’s latest venture will turn viewers off. DiCaprio currently has a 10 percent stake in a new “eco-hotel” being built near Tel Aviv. The 365-room hotel includes commercial spaces, restaurants, and a yacht marina accessible directly through the hotel. How eco-friendly could a 14-story hotel be? Well, it’s being “designed” for “sustainability,” and in 2018 DiCaprio said the project would “serve as a model for environmentally friendly hotel development for the entire world.” But clear climate concerns aside, how eco-friendly can anything be if it’s built on occupied land?

Put aside the actual acting for a minute, and DiCaprio is almost a parody of a famous actor. He courts attention but only in the ways he wants: charity work on a topic almost everyone can agree on (trees = good), but not in a way that impacts his personal relationships with billionaires. He seeks privacy in his dating life while also maintaining a pretty mundanely common one: He’s a man in his 50s who likes young, pretty women. This public performance of morality twined with a greasy romantic history might make DiCaprio feel unwholesome, but the work is so good that it obfuscates any queasiness an audience may have. Maybe his choice of roles is intentional in that way—he can live however he wants so long as the work is superior, and so long as discussion of that work is more interesting than discussion of his personal choices.

But it’s not that Leo didn’t want to be a famous actor, like people said about him when he was in his early 20s and just taking off as the star of Titanic. He did, because the only way to get Gen X–famous was to really want it, and to court it. He just plays the game of aloof artist perfectly, and in a way that no contemporary actor can quite achieve. Guys like Glen Powell or Austin Butler can’t engage audiences by being unknowable the way DiCaprio is, or by avoiding the gaze of the internet. What works for him is the kind of thing that works against a younger actor: distance, disinterest, and disengagement.

In 2015, Martin Scorsese directed a 15-minute-long short film as an ad for the Studio City Macau Resort, featuring DiCaprio along with Brad Pitt and Robert De Niro. DiCaprio and De Niro play slightly less interesting versions of themselves both auditioning for the same role in Manila. De Niro, an established member of the nouveau Rat Pack of the ’70s and ’80s, is quarrelling with the younger but still spiritually similar DiCaprio: two blowhard actors loudly trying to impress a director who came of age during Hitchcock’s prime.

But it’s not a regular ad, is it? It’s a Scorsese ad. A Scorsese film. And even though it’s just an advertisement for some hotel, it somehow feels different. It’s more prestigious. Here’s DiCaprio again, selling you something you don’t need, and likely can’t afford. Somehow, you don’t mind hearing the pitch.