Highlights

  • Diddy's rise to fame happened almost overnight, forming close bonds with legends like Biggie and Tupac.
  • Despite friendships with rap greats like Jay Z and Nas, Diddy has also been in shocking feuds throughout his career.
  • Diddy has strong friendships with celebs like Jennifer Lopez and Will Smith, but also enemies like Aubrey O'Day and 50 Cent.

Sean Combs has been making music since his debut back in 1992, and fans are forever thankful for the work he has contributed to the world of rap. Combs has reshaped the music industry tremendously and has continued to do so for a long time.

Diddy's rise to fame seemingly happened overnight, as he skyrocketed to international fame and success only a year into his career. Considering his talent was as significant as it was, it was no surprise that he became close to rap legends, Biggie and Tupac. While those friendships were cut far too soon, he has managed to continue surrounding himself with like-minded, talented people.

Although he has become close to some of the greatest rappers of our generation, including Jay Z, Kanye West, Nas and Kendrick Lamar, he has also found himself in a multitude of feuds during his career, many of which are quite shocking.

With all that being said, here are 10 celebrities P. Diddy is friends with, and 10 he considers enemies!

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Updated March 2024: Sean "Diddy" Combs may have had his celebrity feuds over the years that have landed him in hot water at times, but nothing like what he is facing currently. Combs had his properties in Los Angeles and Florida raided by Homeland Security on March 25, 2024, due to an ongoing sex trafficking investigation and multiple victims bringing assault and abuse charges against Combs. To date, Combs has denied the allegations and has not been arrested.

20 Friends With: Naomi Campbell

Naomi Campbell and Sean Combs allegedly dated for a time

Naomi Campbell
via Instar

Naomi Campbell and Diddy have been thicker than thieves since the 90s. The two allegedly dated once upon a time. However, neither party wishes to comment on said rumors.

Despite the plausible romance, Naomi and Diddy share a special bond, one that the two have spoken about a number of times, claiming they are the best of friends.

19 Friends With: Jennifer Lopez

Sean Combs and Jennifer Lopez were able to become friends again after breaking up

Jennifer Lopez on the red carpet
via Instar

Combs has dated quite a few high-profile celebrities throughout his career. One of which is none other than Jennifer Lopez.

The two dated in 2000, when Diddy and JLo attended the Grammy Awards where she wore the iconic green Versace dress.

Despite their relationship not working out, the two have remained very close friends, and are spotted hugging and catching up whenever they cross paths.

18 Friends With: Will Smith

Will Smith and Sean Combs started in the music industry at the same time

Will Smith on the red carpet
via Instar

Diddy and Will Smith have found themselves to have quite a close friendship as well! The two debuted in the 90s and were well-versed in the rap industry. In addition to their work, Will and Diddy have been running in the same social circles for over two decades, sharing loads of great times at major parties, events and award shows throughout their careers.

17 (Was) Friends With: Notorious BIG

Sean Combs and Notorious BIG were the tightest of friends until Biggie was killed in 1997

Notorious BIG Juicy music video
via YouTube

When it comes to the world of rap music, there are only a few select artists that have truly shaped the industry forever, and one of those people is none other than Notorious B.I.G. Biggie and Diddy had been tight for nearly a decade prior to his passing, making their friendship one that we and certainly Diddy, won't ever forget.

16 Friends With: Pharrell Williams

Sean Combs and Pharrell Williams formed a friendship out of years of collaboration

Pharrell Williams on the red carpet
via Instar

Pharrell Williams and Diddy have not only collaborated together on a number of songs, but the two have kept things quite tight-knit between them for quite a while. They share a special bond, one that is clearly showcased whenever they are together.

In addition, they both debuted in the same year. However, Pharrell didn't officially come out with his own solo album until 2006.

15 Friends With: Ashton Kutcher

Ashton Kutcher and Sean Combs have been friends since Diddy was on Punk'd

Ashton Kutcher posing on a red carpet
via Instar

If there is one friendship of Diddy's that fans enjoy hearing about, it is with none other than his friendship with actor, Ashton Kutcher.

While the friendship may not be as well-known, Diddy and Kutcher have been friends since Diddy claimed he could not get punked by Kutcher. After he did, the two were instant friends. Ashton even inspired Diddy to run the NYC Marathon!

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14 Friends With: Usher

Sean Combs and Usher have multiple friends in common, which allowed the two to form a friendship

Usher
Via: Instar

When it comes to the music industry, it is safe to say that anybody who is anybody knows one another, and that is the case with Diddy and Usher. Not only are the two musicians close, but apparently, they even used to live together when Usher was 14 years old.

While the two work in different genres and came about at different times, it hasn't stopped them from forming a great friendship over the last decade!

13 Friends With: Lil Kim

Lil Kim and Sean Combs grew up in the music industry together and she is more like family to Diddy than a friend

Lil Kim on the red carpet
via Instar

While Diddy does not let just anybody into his social circle, one person who will always have a spot at his dinner table is Lil Kim.

The two grew up in the industry together, and have regarded each other like family! The two have worked together, performed together and have remained as close together since day one.

12 Friends With: DJ Khaled

After working on The Four together, DJ Khaled and Sean Combs formed a strong friendship

DJ Khaled
Wikimedia Commons

This is a friendship we can definitely get behind! DJ Khaled may be newer to the world of music than Diddy, however, he rose to the top quite quickly. Something Diddy can relate to.

DJ Khaled and Diddy have known one another for quite some time. However, it was their time spent working together on "The Four" that solidified their friendship!

11 Friends With: Mary J Blige

Mary J. Blige and Sean Combs have always had nothing but respect for one another

Mary J. Blige on the red carpet
via Instar

To wrap up the closest friends and relationships to Diddy, Mary J Blige is not to be forgotten!

Mary is hands down one of the most respected women in the world of music, and rightfully so.

Blige and Diddy both debuted in 1992, and have supported each other since the very beginning.

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10 Enemies: Aubrey O'Day

Aubrey O'Day blamed Sean Combs for the breakup of Danity Kane

Aubrey O'Day on the red carpet
via Instar

Diddy and Aubrey O'Day first met during Diddy's time working with Danity Kane, which O'Day was a member of.

Three years after the group was formed, O'Day and another member of the girl band, D. Woods, were fired by Combs. While Combs went on air to say that O'Day's attitude needed to be humbled, in the years since, O'Day claims it was because she refused to "do things" that were expected of her outside of recording and doing interviews to promote the band and the albums. Given all the recent allegations against Diddy, this statement seems to hold a lot more weight.

Most recently, Combs sent the members of Danity Kane NDAs, according to O'Day, so that Bad Boy and Combs would not be spoken about disparagingly in return for the rights to their music.

9 Enemies: 50 Cent

50 Cent and Sean Combs have been feuding for years

50 Cent attends the 2012 American Music Awards
Via: Instar

50 Cent has found himself in verbal altercations with quite a few artists. Combs is one of them.

50 Cent and Diddy have had it out for one another for almost as long as 50 Cent has been in the entertainment industry. Be it the way Diddy dresses, hugs, talks about Notorious BIG, or collaborates with other artists, 50 Cent is not here for it. To say he dislikes Diddy is an understatement.

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8 Enemies: Drake

Drake and Sean Combs got into a physical altercation over a song

Drake on the red carpet
via Instar

Drake has become one of the hottest rappers in the music industry over the last several years. Many even compared the Canadian rapper to Diddy and Jay Z.

While comparing never goes well, it appears things took a bad turn when Diddy and Drake had a physical altercation over a song! The dispute was over the song '0 To 100'. However, Diddy denies the allegations that he ever touched Drake, whereas Drake and other celebs, including Charlemagne tha God, claim that he saw it happen for himself!

7 Danity Kane

"Sexist" comments from Sean Combs to members of Danity Kane caused a rift

Danity Kane on the red carpet
via Instar

Danity Kane looked like they were going to be the next great girl group when they were signed to Bad Boy in 2004. However, in 2008 when O'Day and D. Woods were fired, the dynamic of the group changed. They were never able to recapture the sound the original five had when Diddy signed them.

However, what the group can agree on is that they have encountered "sexist" remarks from Diddy and those around him over the years, at the very minimum. Because of this controversy, Diddy distanced himself from the group, who eventually disbanded in 2009. While there was a brief reunion in 2014, it did not turn out well, and the group broke up again.

In 2020, O'Day, Shannon Bex, and Dawn Richard released new music together under the Danity Kane name but have not done anything since. As such, the status of the group is unknown.

6 Enemies: Jay-Z

Sean Combs and Jay-Z were close until Jay-Z had a fight with Kanye West

Jay Z at The Harder They Fell premiere 2021
Via: Depositphotos

Jay-Z and Diddy have been tight since the two first broke out in the 1990s. Despite their long-lasting friendship though, it appears things went south when Jay-Z and Kanye West, who are both good friends with Diddy, fizzled.

The feud between Jay and Kanye affected Jay's relationship with Diddy negatively. So much so, the two did not talk for three years.

However, the two were spotted catching up at Diddy's 50th in 2019. As such, the two might be friends again.

5 Enemies: Eminem

Eminem wrote a lyric stating that Combs was responsible for Tupac's murder in 1996

Eminem on the red carpet
via Instar

This feud began quite a long time ago, and it appears Eminem went in for a very low blow towards Diddy. Eminem claimed that Diddy had the murder of rap legend, Tupac arranged. Eminem later revealed it was a joke, but Diddy was not laughing one bit. This was a serious accusation, and Eminem took things way too far.

4 Enemies: Kanye West

After being caught in the middle of the fight between Jay-Z and Kanye West, Combs' relationship with West became strained

Kanye West walking
Via Instar

When it comes to the world of rap, artists including Diddy, Kanye, Jay-Z, and various others all keep a tight-knit relationship. However, when things went south between Jay-Z and Kanye West, it appears Diddy got caught in the middle, completely straining his relationship with Kanye West.

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However, the situation was clearly squashed in the years after the falling out, as West attended Diddy's 50th birthday celebration.

3 Enemies: The Recording Academy

Sean Combs believes that the RIAA does not respect music that is put out by Black artists

Sean Combs at the Grammy Awards
via Instar

Diddy has been a staple figure in the music industry since he first debuted back in the early 1990s. He has changed the rap game in ways that have completely reshaped the industry as a whole.

However, when it comes to accepting Grammy's he doesn't think the Recording Academy is on his side, or any black artist for that matter. Diddy called out the Recording Academy in 2020, claiming that 'Black music is not respected by the Grammys'.

2 Enemies: Cassie Ventura

Cassie Ventura and Sean Combs broke up in 2018 and Ventura has since come out with a lawsuit against Combs for abuse and assault

Cassie Ventura at the Grammy Awards
via Instar

Cassie Ventura is without a doubt the woman we all thought would end up with a ring on her finger! But the ten-year relationship between the two finally ended in 2018 after being on and off for years.

In 2023, Ventura filed a lawsuit against Diddy stating that he "often punched, beat, kicked and stomped on [her], resulting in bruises, burst lips, black eyes and bleeding," in addition to sexual abuse, and blowing up Kid Cudi's car after learning that Cudi was romantically interested Ventura.

The case was settled the day after it was filed for an unknown figure.

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1 Enemies: Wendy Williams

Wendy Williams made a comment as a radio host about Sean Combs and he had her fired

What Happened To Wendy Williams?
via: Instar

Wendy Williams is notoriously known for throwing a lot of shade, to a lot of celebrities, and it appears Sean Combs is one of those celebs.

In the 1990s, Williams was a radio host who stated that she believed that Diddy was gay. A comment that did not sit well with Diddy. So much so that he got Williams fired from the station.

Things got tense in 2015 for Williams and Diddy when Williams claimed that Diddy used Ventura as a "possession" rather than a partner.

While Williams said she was over the feud in 2017, the two never reconciled.