The Shady Behaviors That Ruined Leonardo DiCaprio's Reputation Forever

Leonardo DiCaprio was once the prince of Hollywood. A token male ingénue, . 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, . Simultaneously, the movie star's popularity has also declined. Lately, his incomparable acting skills haven't been enough to save his reputation. at the now-infamous 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 . 

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 . Unfortunately for them, Wheatley posted the film online , 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, , 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. .

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 , 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. to protect wildlife and promote conservation efforts. He has worked with several prominent organizations, . DiCaprio has narrated documentaries about climate change and .

An impressive resumé on his part, but DiCaprio has seemingly transitioned from hero to hypocrite. While preaching climate action and , . His relationship with Jeff Bezos has seemingly been the tip of the iceberg. In August 2025, , 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 . 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 .

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."