Leonardo DiCaprio controversial behaviors have drawn intense public scrutiny in recent years, casting a shadow over the actor’s longstanding Hollywood reputation. From questionable social circles in the ’90s to conflicts over his environmental activism and romantic life today, DiCaprio’s actions continue to generate heated discussions throughout 2025.
Despite winning acclaim, including an Academy Award for The Revenant in 2016, DiCaprio’s career and public image have faced significant challenges. His attendance at Jeff Bezos and Lauren Sánchez Bezos’s extravagant wedding in June 2025 sparked outrage due to his friendship with the billionaire, fueling accusations of hypocrisy from environmental advocates. Meanwhile, his recurring pattern of dating much younger women and rumored dismissiveness toward fans have only deepened the controversy surrounding the actor.
Early Career and the Infamous “P***y Posse”
In the late 1990s, Leonardo DiCaprio gained prominence not only through his acting but also as a fixture in New York’s nightlife, where he mingled with figures like Toby Maguire, Kevin Connolly, Lukas Haas, Harmony Korine, and David Blaine. This group, which dubbed themselves the P***y Posse, became notorious for their wild behavior around Manhattan‘s club scene.
Their escapades were captured in the 1996 independent film Don’s Plum, a largely improvised story about a group of friends who regularly met in a Los Angeles diner. Producer Dale Wheatley described the movie as
a love letter to our friends,
according to the New York Post. However, the film’s raw content, including violent outbursts such as DiCaprio’s line,
I’ll f***ing throw a bottle at your face, you godd*** wh*re,
led DiCaprio and Maguire to contest its release legally.
The two actors reached a settlement with producer David Stutan to prevent the film’s distribution, keeping its controversial content out of public view for years. Despite their efforts, Wheatley uploaded Don’s Plum to YouTube in 2016, making the unfiltered glimpse into DiCaprio’s early social life accessible worldwide—a move that resurfaced debate about the actor’s past conduct.
Patterns and Public Perception of DiCaprio’s Relationships
DiCaprio’s personal life has attracted significant attention, especially his long-observed tendency to date women under the age of 25. Throughout his career, this pattern has become so conspicuous that it evolved into a widespread internet meme. High-profile ex-girlfriends like Gisele Bündchen, Blake Lively, and Camila Morrone all reportedly fit within this age range, fueling theories about DiCaprio’s dating preferences.
A Page Six source offered insight into DiCaprio’s reasoning:
By the time girls reach 25, they’re looking for more — they’re looking to get married and settle down,
they explained.
That is not what Leo wants. He does not want a family and does not want to be around women who may press him for that.
However, in 2023, DiCaprio began a relationship with Vittoria Ceretti, who turned 27 in 2025, sparking further online backlash. This deviation from his usual preference caused people to question if the actor’s public image affected his choices or if Ceretti is genuinely an exception. Social media users did not hold back, with one commenting,
Woah she’s over 25, is Leo ok?
and another adding,
Not the 24 years age difference!
This extended age gap has continued to fuel the scrutiny and debate on his dating habits.
Incidents of Disdain Toward Admirers
Despite his fame, DiCaprio has developed a reputation for being distant or even dismissive toward fans who seek his attention. His desire for privacy as an A-list celebrity clashes with fans’ enthusiasm, sometimes resulting in tense encounters. At Paris Fashion Week in June 2025, several fans called out DiCaprio’s behavior, labeling it rude after he reportedly refused multiple photo requests.
This aloofness is not new. In 2005, at Chicago‘s O’Hare airport, DiCaprio refused to sign an autograph for a female fan, telling her,
I don’t sign autographs for anyone anymore – unless I get paid,
as reported by Digital Spy. When she declined to pay, he bluntly said,
Then you’re not getting an autograph.
Such incidents contribute to a public image that many perceive as cold and unapproachable, damaging his relationship with those who admire his work.
The Actor’s Environmental Advocacy Versus Lifestyle Criticism
Leonardo DiCaprio has long been recognized for his environmental activism, founding the Leonardo DiCaprio Foundation in 1998 to support wildlife preservation and conservation programs. His collaborations include partnerships with the Natural Resources Defense Council, the International Fund for Animal Welfare, and the World Wildlife Fund. In 2014, the United Nations appointed him a Messenger of Peace, noting his commitment to climate change awareness.
Despite this record, critics accuse DiCaprio of hypocrisy because his personal lifestyle frequently contradicts his environmental stance. Although championing sustainability, he is known for using private jets and jet skis, activities notorious for high carbon footprints. Particularly controversial was his attendance at Jeff Bezos’s lavish wedding in June 2025, where he attempted to remain inconspicuous but failed to escape online backlash.
In August 2025, DiCaprio and Ceretti accompanied Bezos and Lauren Sánchez Bezos on the billionaire’s luxurious superyacht, which Indiana University scientists calculate produces over 7,000 tons of carbon emissions annually. Such actions sparked widespread criticism across social media platforms, with users commenting on promotional content for DiCaprio’s documentary production:
Hero in movies Villain in real life,
—Instagram user
Amazonia? Or AMAZON?? How was Jeff’s wedding??!!
—Instagram user
The public perception of DiCaprio as an environmental advocate is now fraught with skepticism, highlighting tensions between his philanthropic image and private conduct.
Connection to the Sean “Diddy” Combs Legal Case
Leonardo DiCaprio’s name also surfaced in the high-profile 2025 trial of musician Sean “Diddy” Combs, who faced charges including racketeering and sex trafficking, though Diddy was acquitted of the two latter accusations. Amid the legal proceedings, text messages between Diddy and his former assistant referenced DiCaprio in relation to a poker game.
The assistant wrote to Combs,
Leo [DiCaprio] grabbed my pink bedazzled BlackBerry, and you said that Titanic mother f***er doesn’t know s***. He won 10K, I won 650K.
This casual mention connected DiCaprio to the social circles under scrutiny during the trial.
DiCaprio’s association with Diddy dates back further, as photos revealed the actor attending Diddy’s famous White Parties in 1998. In a 2017 Vogue interview, Diddy spotlighted DiCaprio as the top invitee for the resurgence of these parties. When asked,
Who’s the person that’s number one on the invitation list?
Diddy answered with DiCaprio’s name, confirming the longstanding relationship between the two celebrities.
This connection has invited additional criticism online, with one X user sardonically noting,
Makes sense considering the age group he prefers.
DiCaprio’s social and professional affiliations continue to fuel debate about his character and choices.
Current Public Standing and Future Challenges
Leonardo DiCaprio controversial behaviors present a complex image of a celebrated actor whose personal and professional lives clash with public expectations. His once untouchable status appears eroded by accusations of hypocrisy, especially regarding environmental matters, mixed with his contentious behavior in social and romantic spheres.
As internet backlash intensifies, DiCaprio faces mounting pressure to reconcile these contradictions. The evolving narrative surrounding him suggests that the Hollywood actor’s future may depend on how he addresses these controversies, both in the public eye and through his actions.
With ongoing scrutiny from fans and critics alike, the impact on DiCaprio’s career and legacy remains uncertain, signaling a pivotal moment for one of Hollywood’s most recognizable figures.
