The Shady Behaviors That Ruined Leonardo DiCaprio's Reputation Forever

Leonardo DiCaprio was once the prince of Hollywood. A token male ingénue, DiCaprio dominated the '90s film scene and has had an impressive resume over the years. He even received a well-earned Academy Award for his work in "The Revenant" in 2016. Suffice it to say, DiCaprio has made an indelible impression on the industry. However, his talent hasn't dismissed his questionable behavior over the years.

In the last decade, we've seen a downturn in his activity in Hollywood. Simultaneously, the movie star's popularity has also declined. Lately, his incomparable acting skills haven't been enough to save his reputation. In June 2025, DiCaprio was seen burying his head in a baseball cap to conceal his appearance at the now-infamous wedding of Jeff Bezos and Lauren Sánchez Bezos, which totaled over $50 million. His friendship with the billionaire incentivized internet users to get out their pitchforks and torches, crying hypocrisy against the well-known environmentalist. Not only that, DiCaprio's dating history has been rendered a meme, with Sabrina Carpenter even putting his face on a cake when she turned 25. 

Could this be the downfall of the Hollywood royal? These problematic actions over the years might be taking its toll on his career and rep. 

With a certain cachet acquired from his early acting days, Leonardo DiCaprio became somewhat of a nocturnal legend in the New York club scene by the late '90s and early 2000s. He hung out with the likes of Toby Maguire, Kevin Connolly, Lukas Haas, Harmony Korine, and David Blaine, among others, according to a 1998 profile from New York Magazine. DiCaprio and his pack wreaked havoc across Manhattan, proclaiming themselves as the "P***y Posse." It's not a name that could fly in today's culture, which is likely why the "Shutter Island" actor attempted to sweep many details of their group under the rug.

The posse's antics were documented in a 1996 low-budget, low-profile indie film called "Don's Plum." The flick was largely improvised, with producer Dale Wheatley once calling it "a love letter to our friends," per the New York Post. The film took place in a Los Angeles diner, where a group of friends — played by the posse — met every week with a new set of women. One line illustrates one theme of the production, with DiCaprio yelling, "I'll f***ing throw a bottle at your face, you godd*** wh*re." That line is likely one of the many reasons DiCaprio, along with Maguire, settled in court against David Stutan, another of the film's producers, to ensure that their project never saw the light of day. Unfortunately for them, Wheatley posted the film online in 2016, and now it is accessible to anyone on YouTube.

Leonardo DiCaprio's suave, Romeo-esque charm is why a cliché number of women flocked to him in his 20s. However, the Hollywood great has maintained his bachelor attitude into his 50s — and yet, the women have stayed the same age. DiCaprio's dating history has now snowballed into a phenomenon, which theorizes that he refuses to date any women older than 25. A Reddit user even made a chart to show that the ages of his previous girlfriends — including Gisele Bündchen, Blake Lively, Camila Morrone, and more — were capped at 25 years old. According to a source who spoke to Page Six, DiCaprio has a reason for his serial dumping. "By the time girls reach 25, they're looking for more — they're looking to get married and settle down," they revealed, adding, "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."

In a shocking turn of events, however, DiCaprio has been with his girlfriend, Vittoria Ceretti, since 2023, with Ceretti having turned 27 in 2025. Has DiCaprio been influenced by the incessant vitriol about his love life, or has he actually found the one? Perhaps both? Nonetheless, their massive age gap is still fueling internet trolls. "Woah she's over 25, is Leo ok?" one Instagram user wrote. "Not the 24 years age difference!" another said. Needless to say, two years above his usual age range is still a cringeworthy number.

No matter how much Leonardo DiCaprio yearns for a normal life, his A-lister status inhibits such privacy. It might be the reason why DiCaprio seemingly has a reputation for being cold toward his devoted fans, who wait for him outside of airports and cafés, just for a chance to see his face and maybe even snag a selfie. Unfortunately for those seeking a moment with the star, DiCaprio reportedly doesn't hand out freebies. During Paris Fashion Week in June 2025, fans deemed him rude after DiCaprio reportedly shunned a flock of admirers asking for photos.

He has been infamously dismissive toward his fans from the get-go. In 2005, a female Leo lover approached the actor at Chicago's O'Hare airport, looking for an autograph. However, DiCaprio refused to give her the time of day. "I don't sign autographs for anyone anymore – unless I get paid," DiCaprio reportedly told her (via Digital Spy). When she wouldn't compensate the millionaire actor, he reportedly told her, "Then you're not getting an autograph."

Leonardo DiCaprio has championed environmental advocacy for as long as he has had influence. In 1998, at 24 years old, DiCaprio launched the Leonardo DiCaprio Foundation to protect wildlife and promote conservation efforts. He has worked with several prominent organizations, including the Natural Resources Defense Council, International Fund for Animal Welfare, and the World Wildlife Fund. DiCaprio has narrated documentaries about climate change and was even named a United Nations Messenger of Peace in 2014.

An impressive resumé on his part, but DiCaprio has seemingly transitioned from hero to hypocrite. While preaching climate action and sustainability, DiCaprio has had no problem cruising on jet skis and flying private over the years. His relationship with Jeff Bezos has seemingly been the tip of the iceberg. In August 2025, DiCaprio and Vittoria Ceretti joined Bezos and Lauren Sánchez Bezos on the Amazon founder's multi-million-dollar superyacht, which, according to Indiana University (via the New York Post), produces over 7,000 tons of carbon emissions.

The public isn't letting him get away with it. A promotional video for a documentary DiCaprio produced is being flooded with comments on social media about the hypocrisy of his lifestyle. "Hero in movies Villain in real life," someone wrote on Instagram. Another said: "Amazonia? Or AMAZON?? How was Jeff's wedding??!!"

The disturbing allegations against Sean "Diddy" Combs were assessed in the rapper's 2025 trial, after being indicted on charges including racketeering and sex trafficking (two charges on which he has since been found not guilty). Many A-listers were named during the high-profile trial, including  Leonardo DiCaprio. Text messages between Diddy and his ex-assistant mention DiCaprio's name in the context of a poker game. The former Diddy employee wrote in a message to her boss (via Fox News): "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." The "Don't Look Up" actor's interactions with the rapper seemingly went beyond games of poker, with resurfaced images from Diddy's infamous "White Parties" revealing DiCaprio's attendance at least one in 1998.

Photos from Diddy's all-white parties.

What do you notice? pic.twitter.com/7X24z14rIJ

— Creepy.org (@creepydotorg) October 28, 2024

In a 2017 interview with Vogue, Diddy even name-dropped DiCaprio as a guest at the "White Parties." When he told the interviewer that his parties were going to make a comeback, the man behind the camera asked, "Who's the person that's number one on the invitation list?" Diddy gave one name: "Leonardo DiCaprio." DiCaprio has received a lot of flak from people online since, with one X, formerly Twitter, user even harshly musing, "Makes sense considering the age group he prefers."