For 3 a long time, Leonardo DiCaprio appeared untouchable, the concept of his downfall some sarcastically inconceivable punchline. Along with his boyish visage emblazoned upon a plethora of posters hugging the partitions of worldwide bedrooms and dorm rooms, the actor was Jay Gatsby for millennials and Romeo for Gen X. DiCaprio first burst onto the cultural zeitgeist on the age of 19 courtesy of the 1993 films “This Boy’s Life” (reverse longtime collaborator Robert De Niro) and “What’s Consuming Gilbert Grape” (reverse Johnny Depp). He earned Oscar and Golden Globe nominations for the latter, rapidly changing into Hollywood’s “it” boy of the ’90s because of “Romeo + Juliet,” “The Basketball Diaries,” and “Titanic.”

In a transfer to transcend his youthful intercourse image standing, DiCaprio gravitated towards darker roles and acclaimed administrators, reminiscent of Steven Spielberg, Christopher Nolan, Quentin Tarantino, and Ridley Scott. It was his collaborative relationship with filmmaker Martin Scorsese, although, that may dominate DiCaprio’s profession as a number one man, starting with 2002’s “Gangs of New York” and increasing throughout seven movies since. Within the midst of all of it, he received the Academy Award for Greatest Actor because of his grueling bodily efficiency within the 2015 movie, “The Revenant.” As soon as deemed the “Prince of the Metropolis” by New York Journal, DiCaprio had change into “king of the world.”

Issues look rather a lot totally different for DiCaprio 10 years after that Oscar win. He is solely appeared in three movies over the previous decade, with arguably extra consideration paid to his private life than his work.

The cultural panorama had a a lot totally different topography within the Nineteen Nineties than it does at this time, and arguably a way more sexist one at that. In these post-MeToo occasions, it is virtually unimaginable to think about a preferred actor getting away with main a self-described “P***y Posse” because it charged its approach by the world’s nightclubs like some irascible bull. Nevertheless, that is precisely what Leonardo DiCaprio did within the Nineteen Nineties and a part of the following decade, alongside fellow posse members Tobey Maguire, Lukas Haas, Kevin Connolly, David Blaine, Concord Korine, and others.

That ribald habits was mirrored within the underseen and semi-improvised movie “Don’s Plum,” starring posse members DiCaprio, Maguire, and Connolly. Filmed in 1995 and 1996, earlier than the actors’ most titanic successes, the black-and-white indie showcased the uncooked, nastier facet of the group. It apparently revealed a lot of their misogynistic “P***y Posse” habits that each DiCaprio and Maguire have actively fought to forestall the movie’s launch. They’ve claimed that “Don’s Plum” was made as a favor to a buddy and wasn’t supposed to be launched as a function. After David Stutman, one of many movie’s producers, alleged that they used their clout to dam its distribution, the 2 actors ended up settling for $10 million in an settlement which allowed for a restricted launch outdoors North America. That is necessary as a result of the movie (and lawsuit) previewed the habits that may result in DiCaprio’s descent.

It is one factor for Leonardo DiCaprio to social gathering with the “Pussy Posse” in his 20s, however that dance of debauchery seems to be totally different once you’re 50. A part of DiCaprio’s downfall is because of the truth that he is possible by no means shed his “Don’s Plum” days. Equally, courting a 17-year-old once you’re 20 (as DiCaprio reportedly did with Bridget Corridor in 1994) is extra socially acceptable than courting a 19-year-old once you’re 48, as DiCaprio was rumored to have achieved with Eden Polani. Enjoying Romeo begins to put on skinny at 50.

DiCaprio developed an unsavory status for courting fashions as much as the age of 25, churning by Victoria’s Angels like a human guidelines. DiCaprio’s age-gap relationships have been derisively known as Leo’s Regulation, and there was even a viral graph on Reddit that charts his doubtful courting historical past. Ladies who dated DiCaprio earlier than turning 25 embrace Bridget Corridor, Kristen Zang, Amber Valletta, Bijou Phillips, Gisele Bundchen, Anne Vyalitsyna, Blake Vigorous, Erin Heatherton, Toni Garrn, and Victoria Lamas. DiCaprio’s relationships with Bar Refaeli, Nina Agdal, and Camila Morrone ended shortly after they turned 25.

To paraphrase a line from Matthew McConaughey’s character within the movie “Dazed and Confused,” Leo will get older, they keep the identical age. Granted, Leo’s Regulation has exceptions to show the rule, specifically his relationship with 27-year-old Vittoria Ceretti. Nonetheless, DiCaprio continues to be ridiculed for what’s thought of his creepy tendencies.

Leonardo DiCaprio’s playboy historical past is just one ingredient of a seemingly extravagant way of life that has come below scrutiny over the previous decade, with the 50-year-old nonetheless partying prefer it’s 1999. Maybe it is merely a matter of envy, however the actor’s exorbitant, jet-setting methods have been criticized as not only a extended mid-life disaster however blatant hypocrisy, contemplating DiCaprio’s lifelong environmental advocacy and local weather change activism. The actor has been a notable voice in that motion, typically fairly actually, having narrated and co-produced a number of documentaries about local weather change. DiCaprio’s ardour for environmental causes has solely motivated his critics additional, who declare the actor hardly practices what he preaches.

DiCaprio’s frequent use of personal jets — which pollute as much as 14 occasions greater than business airways, in line with TIME – initially got here below fireplace in 2016 (arguably “12 months One” of DiCaprio’s downfall). That is when DiCaprio took a personal jet from Cannes to New York so as to obtain an environmental award from clean-water advocate Riverkeeper. He flew again to Cannes inside 24 hours, and the subsequent day took one other non-public jet to journey lower than eight miles, attending a gala in Antibes.

As if that wasn’t sufficient, DiCaprio events year-round on environmentally ruinous superyachts and was as soon as criticized for actually taking a helicopter from his yacht to dine and wine at a restaurant, in line with The Toronto Solar. Leo loves women and liquor, in any case.

Regardless of his obvious hypocrisy and the damaging indicators it sends, Leonardo DiCaprio has nonetheless raised some huge cash for environmental causes — or has he? The Leonardo DiCaprio Basis (LDF) was arrange in 1998 for a wide range of conservation efforts, however was comparatively small till becoming a member of the California Group Basis as a donor-advised fund (DAF) in 2008. Changing into a DAF has allowed the muse to keep away from transparency, making it virtually unimaginable to glean its precise funds. In line with the IRS, donor-advised funds can be utilized for “questionable charitable deductions” and “impermissible financial advantages to donors.”

All this has gotten the LDF and DiCaprio himself in scorching water with the federal government. In 2016, the LDF raked in a whopping $45 million in donations throughout only one gala on July 20, the place DiCaprio mingled with oligarchs reminiscent of Mohammed Al Turki and Dmitry Rybolovlev, and A-listers like Bono, Robert De Niro, Scarlett Johansson, and Arnold Schwarzenegger. That very same day, the Division of Justice filed a criticism investigating a large embezzlement case which concerned the LDF and DiCaprio, who was named as “Hollywood Actor 1,” however not charged.

The DOJ alleges that DiCaprio’s basis was used to embezzle tens of millions of {dollars} from a Malaysian sovereign wealth fund truly supposed for oil exploration, all as a part of “the biggest kleptocracy scheme thus far,” in line with the FBI. And DiCaprio was tight with the person behind all of it — Jho Low.

Leonardo DiCaprio and his basis each benefited vastly from a mysterious man named Low Taek Jho (aka Jho Low), the supposed mastermind behind the 1MDB scandal, which refers back to the billion-dollar Malaysian sovereign wealth fund. A tough-partying massive spender, Low would’ve match proper into DiCaprio’s “Pussy Posse,” however as a substitute of conventional handsomeness and Hollywood success, Low had cash, and many it. “Billion Greenback Whale,” a e book concerning the present fugitive from justice, alleges that Low spent $85 million on events between October 2009 and June 2010 alone. Siphoning tons of of tens of millions of {dollars} from the Malaysian state, Low paid DiCaprio a $250,000 price to hitch him, in line with ongoing federal investigations.

Starting in November 2009, DiCaprio was paid to social gathering internationally with Low, together with an $11 million “playing bender” in Vegas, in line with The Hollywood Reporter. Low and his associates supposedly gifted DiCaprio a $9.2 million Basquiat portray, a $3.2 million Picasso, and Marlon Brando’s Academy Award for “On the Waterfront,” which was bought for $600 thousand (by way of Artnet); DiCaprio needed to give up these things to the federal government.

Maybe the weirdest a part of DiCaprio’s relationship with Low is the truth that the latter supplied monetary backing for the previous to painting an notorious monetary felony. Irony of ironies, Low contributed tens of millions of (possible embezzled) {dollars} to assist finance “The Wolf of Wall Avenue.” But, it is uncertain that DiCaprio can give up to the federal government the acclaim he obtained for that movie.

Whereas Jho Low would be the most infamous amongst them, Leonardo DiCaprio has gotten shady by proxy because of relationships which have contributed to the deterioration of his status. A number of of those scandalized collaborators had been concerned in Crimson Granite Footage, which helped produce “The Wolf of Wall Avenue” and later paid $60 million to settle an investigation into its involvement with Low and the 1MDB scandal. They embrace producers Joey McFarland, who needed to forfeit $14 million in earnings and presents to the federal government, and Riza Aziz, who needed to forfeit $107 million. Each males obtained a shoutout from DiCaprio throughout his Golden Globes acceptance speech in 2014, saying, “Joey, Riz and Jho, thanks for not solely being collaborators, however for taking a threat on this film.”

The entire 1MDB scandal even introduced DiCaprio to the courtroom, the place he was ordered to testify in a federal trial involving Low, embezzlement, and Prakazrel “Pras” Michel, a founding member of The Fugees. Michel, who usually partied with DiCaprio and Low, was convicted on 10 counts concerning the funneling of cash from the Malaysian authorities’s sovereign account. DiCaprio testified that he’d first met Michel backstage at a live performance within the late ’90s, and stated of Low, “I used to be given the inexperienced mild by my group in addition to my studio,” in line with The Guardian. “He was a authentic enterprise individual eager to spend money on the film.”

Dana Giacchetto was a fair shadier determine in Leonardo DiCaprio’s posse. Dubbed “the stockbroker to the celebs,” Giacchetto handled myriad main megastars and their tens of millions. “Leo DiCaprio is like my little brother,” Giacchetto advised The Hollywood Reporter in April 2014, regardless of being sentenced to 57 months in jail for fraud in 2000 and reportedly dropping cash for purchasers, together with DiCaprio. Earlier than that, although, DiCaprio was deep with Giacchetto, even dwelling in his SoHo loft within the late ’90s. DiCaprio skipped the 1998 Oscars (which “Titanic” swept) to as a substitute social gathering with Giacchetto.

Giacchetto was a member of DiCaprio’s “P***y Posse,” which tailored to extra politically appropriate occasions by rebranding because the “Wolf Pack.” Members even had an precise necklace replete with a howling wolf pendant. Artwork supplier Helly Nahmad was one other member, and one more shady buddy who ended up in jail.

A detailed buddy of DiCaprio’s, Nahmad was accused of being a part of a multi-million-dollar cash laundering scheme involving high-stakes poker video games attended by DiCaprio and others. His 2014 plea deal led to Nahmad paying greater than $6.4 million and receiving three years of probation after his jail sentence. Nevertheless, Nahmad was later pardoned by Donald Trump on the finish of his first administration; Nahmad additionally occurs to personal the 51st ground of Trump Tower in New York. Nonetheless, DiCaprio continued to social gathering along with his buddy, boarding a personal jet with him in 2023 (by way of the Each day Mail).

As if Leonardo DiCaprio’s relationships with shady pals (and a few downright criminals) weren’t sufficient, the actor’s public status would undergo an additional extreme blow after his title was dragged into the Sean “Diddy” Combs controversy. Whereas the media was specializing in the fallen rap star’s intercourse trafficking and racketeering trial, older images resurfaced, which revealed DiCaprio laughing and smoking with Diddy throughout certainly one of his so-called “White Events,” held yearly from 1998 to 2009.

Individuals additionally pointed to a 2017 Vogue video interview the place Diddy claimed that he would revive the White Events. The reporter asks, “Who’s the individual that’s primary on that invitation record?” Diddy replies with only one title – “Leonardo DiCaprio.” The actor’s title additionally got here up in textual content messages that had been a part of the courtroom proceedings, in line with Fox Information, being talked about by Diddy’s ex-assistant concerning a high-stakes poker recreation. “Leo [DiCaprio] grabbed my pink bedazzled BlackBerry, and also you stated, ‘That Titanic mom f***er would not know s***. He received 10K, I received 650K.'”

Diddy’s White Events and poker video games don’t implicate DiCaprio in any approach concerning the “freak-offs” and felony allegations. Nonetheless, DiCaprio’s bruised status and public downfall have made it straightforward for denizens of the web to take a position concerning the extent of DiCaprio’s connections. “Is smart contemplating the age group he prefers,” wrote one X consumer on the time, echoing the feelings of many social media customers (by way of FandomWire).

Alan Thicke, Leonardo DiCaprio’s one-time co-star in “Rising Pains,” advised The Washington Submit in 2015, “Leo is a type of guys everybody rooted for … nearly anybody would inform you they get pleasure from celebrating by proxy.” Effectively, that was simply earlier than the aforementioned “12 months One” of DiCaprio’s downfall, and at this time, even a seemingly innocuous picture of the actor having fun with a Wimbledon tennis recreation brings out on-line haters.

On July 11, 2025, the Wimbledon X (previously Twitter) account posted a picture of DiCaprio, Rolex on wrist, sitting within the bleachers throughout a tennis match, captioning the {photograph} by writing, “Leonardo DiCaprio having fun with a Titanic tussle at SW19.” That is all, no extra, no much less. Regardless, the remark part included a wide range of unfavorable criticism concerning the actor, from jokes about his courting life to his perceived environmental hypocrisy. “Pretend environmentalist who loves his massive non-public jets and yacht events,” commented one consumer. “Leo attending Wimbledon to witness Novak’s #25 after which he’ll cease watching tennis,” wrote one other. “Did local weather pillock use a personal jet or a diesel powered yacht to get there?” requested a critic.

Whereas there have been actually some impartial and even constructive feedback, the truth that a very harmless and arbitrary picture of DiCaprio garners a lot hate as of late some see this as clear proof of the actor’s public downfall.  Some tweets summarizing the general sentiment of the remark part: “High Diddy Shopper,” “The place’s his buddy Jho Low?” and “Ewww creep.”

Nowadays, Leonardo DiCaprio appears to acknowledge the contempt with which the general public perceives him. That is in all probability why he makes an attempt to obfuscate his look when he is out and about, particularly when he is participating in his most critiqued habits, sometimes carrying a masks and a darkish baseball cap that is pushed additional down than Chuck Schumer’s glasses. As an illustration, the famous environmentalist was berated for attending the lavish marriage ceremony of Lauren Sanchez and Jeff Bezos. Regardless of actively making an attempt to keep away from recognition, virtually carrying his hat on prime of his face, DiCaprio was nonetheless lambasted for his determination.

DiCaprio was certainly one of many celeb friends on the three-day marriage ceremony, which reportedly price round $20 million. That is barely a fraction of a share of what Bezos had constituted of founding Amazon, one of many world’s greatest polluters, with its manufacturing of 16.2 million metric tons of carbon dioxide every year. That is particularly why DiCaprio was criticized for his attendance, contemplating how vocal he has been about local weather change advocacy. “I’ve had two nice passions in my life. That has been appearing, and the safety of the pure world and getting the message out concerning the local weather disaster,” DiCaprio advised Deadline in 2022. “I believe there is a worldwide sense of hysteria about the truth that the powers that be, the non-public sector, governments, do not make the transition quick sufficient.” Apparently, DiCaprio exempts Bezos from “the powers that be.”

Maybe much less focus can be positioned on Leonardo DiCaprio’s private life and connections if he truly starred in additional films. On the time of writing, he has solely appeared in three movies over the previous decade, starting with ’12 months One’ of the actor’s downfall. He obtained various quantities of popularity of these footage (“As soon as Upon a Time in Hollywood,” “Do not Look Up,” and “Killers of the Flower Moon”), which usually distract DiCaprio’s disdainful detractors when they’re launched. Even those that dislike DiCaprio’s performances usually need to admit that he stars in high-quality films.

Despite the fact that he is making fewer movies than ever, and regardless of his ongoing public downfall, DiCaprio continues to be demanding unrealistic quantities of cash for them, often between $20 and $30 million for lead performances. The actor has been in pay disputes over his small look within the proposed sequel to “As soon as Upon a Time in Hollywood,” turning down $3 million for simply at some point of filming. Possibly that is one of many explanation why another celebrities cannot stand him.

It stays to be seen whether or not DiCaprio’s latest movie, “One Battle After One other,” will sway public discourse in any approach. Contemplating the virtually audible groans each time DiCaprio is talked about as of late, it might be honest to say his downfall is everlasting. Then once more, there’s all the time time to develop up, even in your 50s.