Since Sean “Diddy” Combs was one of the most powerful people in the music business for years, a lot is known about him. Fans know about who Diddy’s children are, what it was like to work for him, which legends he partied with, and about his strange relationship with 50 Cent. After Diddy’s homes were raided, people also found out about his enemies and about which stars would still support him. However, many observers still don’t know about Diddy’s relationship with Leonardo DiCaprio.
Of course, Leonardo has starred in so many hit movies that he’s become very rich and the media has obsessed over his personal life. Despite that, most observers have no idea that Leonardo has an embarrassing past with Diddy.
Diddy And Leonardo DiCpario Have A Well-Documented History Which Is Embarrassing Now
For many years, it seemed very clear that Sean “Diddy” Combs was one of the celebrities with the most connections. At that time, most people didn’t question things when they learned that Diddy was hanging out with their favorite celebrity.
Then, a series of accusations about the disturbing things that happened at so-called Diddy parties changed that forever. That only got worse when the authorities raided Diddy’s home, which was followed up by the rapper being arrested and put in prison.
Now, it is very clear that celebrities don’t want to be associated with Diddy in any way. That is a problem for some celebrities, like Leonardo DiCaprio who has a well-documented history with Diddy.
Over the years, there have been several times when it became clear that Diddy and Leonardo DiCaprio have a history of hanging out.
Which Celebrities Defended Diddy After At Least Some Of The Accusations Went Public, According to XXL Magazine?
- Slim Thug
- Uncle Luke
- Stevie J
- Floyd Mayweather
- Akon
- Tyrese Gibson
- Jason Derulo
One example of that is the fact that a September 2023 Daily Mail article featured a photo of Diddy and Leonardo together. That photo shows an obviously younger Leonardo and Diddy at one of the rapper’s white parties. Leonardo notably has a big smile on his face in the photo.
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While that photo of Leonardo DiCaprio and Diddy is noteworthy, it isn’t that meaningful taken on its own. However, there is other evidence that seems to indicate the duo had a lasting association.
Diddy’s 2023 and 2024 Lawsuits, According to Vulture | |
|---|---|
Lawsuit | Date Filed |
Cassandra “Cassie” Ventura V. Sean Combs | November 16, 2023 |
Liza Gardner V. Sean Combs | November 23, 2023 |
Joi Dickerson-Neal V. Sean Combs | November 23, 2023 |
Jane Doe V. Sean Combs | December 2, 2023 |
Rodney Jones V. Sean Combs | February 2, 2024 |
Grace O’Marcaigh V. Sean Combs | April 4, 2024 |
For example, People reported in December 2019 that Leonardo attended Diddy’s 50th birthday party. While Leonardo almost certainly wouldn’t want that to be focused on, him attending Diddy’s 50th birthday party isn’t necessarily that meaningful.
Leonardo going to Diddy’s 50th birthday doesn’t seem that noteworthy because of a YouTube video. In December 2019, Diddy published a video on his YouTube channel showing highlights of his 50th birthday party. There were so many celebrities shown in that footage that it would take too much space to list them all here.
It is also known that Diddy and Leonardo were together at another star-studded event because of Liam Payne.
According to
Britannica
, Sean “Diddy” Combs was born on November 4, 1969, which makes him 54 years old as of January 2025.
Britannica
also reports that Leonardo DiCaprio was born on November 11, 1974 and is 50 years old as of January 2025. That means that Diddy is five years and seven days older than Leonardo.
In May 2017, Liam appeared on The Graham Norton Show, as can be seen in a YouTube clip of his appearance. During his appearance on the celebrated talk show, Liam spoke about approaching Diddy, Jay-Z, and Leonardo.
I went over to say hello to P. Diddy and Jay-Z was there and, Leonardo DiCaprio sat at the door.
In addition to the reports about them, Diddy has also spoken about Leonardo during interviews.
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During interviews, Diddy spoke about partying with Leonardo on more than one occasion.
In September 2023, Yahoo! Entertainment reported on Diddy’s much-talked-about white parties. That article quoted from an interview Diddy gave to Oprah Winfrey that is no longer on her website. During that interview, Diddy spoke about partying with Leonardo as far back as the late-’90s.
“I had the craziest mix: some of my boys from Harlem; Leonardo DiCaprio, after he’d just finished
Titanic
. I had socialites there and relatives from down south. There were 200 people sitting out here, just having a down-home cookout.”
More than a decade later, Diddy again brought up partying with Leonardo during an interview. In December 2017, Diddy was asked 73 questions by Vogue, as can be seen in a YouTube upload of the discussion.
During the interview, Vogue’s interviewer stated that Diddy was preparing to have one of his white parties for the first time in a while. The interviewer then asked Diddy who the number one person to be invited to the party would be. In response, Diddy revealed that Leonardo was the first person he would invite to his party.
It is fascinating to note that Diddy said he was partying with Leonardo after Titanic was filmed, and he was going to invite him to a party in 2017. That would mean that Diddy and Leonardo were associated on some level for three decades. At least, it would mean that if Diddy’s claims about Leonardo were true.
Leonardo DiCaprio Reportedly Wasn’t As Close With Diddy As It Might Have Seemed
Despite all the evidence that Leonardo DiCaprio and Diddy have repeatedly hung out over the years, that doesn’t really prove much. After all, Diddy was never shy about name-dropping, and they could have only hung out a handful of times.
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In September 2024, The Daily Mail published a report about Diddy and Leonardo’s relationship. That article cited an insider who told the outlet that Leonardo and Diddy had “not been in contact” for years. Furthermore, the insider stated that the extent of their relationship was that Leonardo only went to a few of Diddy’s parties a long time ago.
“He attended a few of his parties back in the early 2000s — but literally everyone did. They were not freak offs. They were big house parties.”
While talking to The Daily Mail about the two men’s past relationship, the insider stated that Leonardo wasn’t involved in Diddy’s accusations. The insider also stated that Leonardo didn’t party like he used to, and he’d moved on with his life.
“Leonardo DiCaprio has absolutely nothing to do with any of this… [Leo] as moved way past his partying. He has nothing to do with any of that world, so for anyone to assume that he will get roped into this based on a few grainy photos that are more than 20 years old is ridiculous. Leo is focused on his career and his relationship and is not at all thinking about Diddy’s federal case, which he has nothing to do with.”
Based on the evidence that is publicly available, it certainly seems like part of the claims made by that insider aren’t true. After all, People reported that Leonardo attended Diddy’s 50th birthday party in 2019, which is a lot more recent than the early 2000s. That said, the main point that the insider was making can still be true.
Sean Combs – Diddy
- Birthname
- Sean John Combs
- Birthdate
- November 4, 1969
- Birthplace
- Harlem New York, NY
- Family
- Justin Dior Combs , Chance Combs , Jessie James Combs , King Combs , Love Sean Combs , D’Lila Combs
- Notable Allies
- The Notorious B.I.G.
- Height
- 5’10”
- @diddy
- Siblings
- Keisha Combs
- Parents
- Melvin Earl Combs, Janice Combs
- Net worth
- $800,000,000
- Professions
- Rapper , Musician
- Source of Wealth
- Actor, Fashion designer, Record producer, Singer, Film Producer, Television producer, Rapper, Entrepreneur, Musician, Screenwriter
- Nationality
- American
